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Advanced Dairy Chemistry pp 121–201Cite as

Galacto-oligosaccharides and Other Products Derived from Lactose

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Abstract

Lactose is the precursor for a number of compounds derived by chemical, physical or enzymatic conversion that have an established and expanding place in the health and food industries. These include lactulose and galacto-oligosaccharides both of which are manufactured in large tonnages worldwide. Lactitol and lactosucrose are produced commercially, but in much smaller amounts, while lactobionic acid is produced for limited industrial and medical applications and for research use. The only other lactose derivative of commercial interest is an isomer of galactose called tagatose in which there is an emerging interest as a sweetener.

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References

  • 3A Business Consulting. 2005. Global market analysis of whey and lactose products 2004–2009 (report published November 2005) J.M. Morks Gade 1, DK-8100 Aarhus C, Denmark.

    Google Scholar 

  • AACC. 2001. The definition of dietary fiber. Report of the Dietary Fiber Definition Committee to the Board of Directors of the American Association of Cereal Chemists. Cereal Foods World 46, 112–126.

    Google Scholar 

  • AACC. 2002. Method 32-33. Determination of trans-galacto-oligosaccharides in selected food products by ion- exchange chromatographic method. In: Approved Methods of the American Association of Cereal Chemists, 10th edition, p. 8.

    Google Scholar 

  • Abbadi, A., Gotlieb, K.F., Meiberg, J.B.M., Peters, J.A., Van Bekkum, H. 1999. New Ca-sequestering materials based on the oxidation of the hydrolysis products of lactose. Green Chem. 1, 231–235.

    Article  CAS  Google Scholar 

  • Adlerberth, I. 1999. Establishment of a normal intestinal microflora in the newborn infant. In: Probiotics, Other Nutritional Factors and Intestinal Microflora (L.A. Hansen, R.H. Yolken, eds.), pp. 63–78, Nestle Nutrition Workshop Series, Vol. 42, Nestec Ltd, Vevey. Lippincott-Raven, Philadelphia.

    Google Scholar 

  • Akiyama, K., Takase, M., Horikoshi, K., Okonogi, S. 2001. Production of galactooligosaccharides from lactose using a β-glucosidase from Thermus sp. Z-1 – recombinant production of thermostable β-glucosidase, purification, and use in galacto-oligosaccharide preparation, Biosci. Biotechnol. Biochem. 65, 438–441.

    Article  CAS  Google Scholar 

  • Alander, M., Matto, J., Kneifel, W., Johansson, M., Kogler, B., Crittenden, R., Mattila-Sandholm, T., Saarela, M. 2001. Effect of galacto-oligosaccharide supplementation on human faecal microflora and on survival and persistence of Bifidobacterium lactis Bb-12 in the gastrointestinal tract. Int. Dairy J. 11, 817–825.

    Article  CAS  Google Scholar 

  • Anon. 1997. Lactulose. Brochure of Morinaga Milk Industry Co., Ltd., Tokyo, Japan.

    Google Scholar 

  • Anon. 2003. Material Safety Data Sheet for Lactulose Concentrate, rev. 2, dated 18 Sept. 2003, Canlac Division of Solvay Pharma, Quebec, Canada.

    Google Scholar 

  • Asp, N.G., Burval, A., Dahlquist, A., Hallgren, P., Lundblad, A. 1980. Oligosaccharide formation during hydrolysis of lactose with Saccharomyces lactis lactase (Maxilact ®). II. Oligosaccharide structures. Food Chem. 5, 147–153.

    Article  CAS  Google Scholar 

  • AOAC International. 2006. Official Methods of Analysis, 18th edition revised. Method 2001.02.

    Google Scholar 

  • Bailey, R. (2008). Japan: An established market for nutraceuticals. Nutraceuticals World Nov. 2008.

    Google Scholar 

  • Bailey, R.W. 1965. Oligosaccharides, Pergamon Press, Oxford.

    Google Scholar 

  • Bakker-Zierikzee, A.M., Alles, M.S., Knol, J., Kok, F.J., Tolboom, J.J.M., Bindels, J.G. 2005. Effects of infant formula containing a mixture of galacto- and fructo-oligosaccharides or viable Bifidobacterium animalis on the intestinal microflora during the first 4 months of life. Br. J. Nutr. 94, 783–790.

    Article  CAS  Google Scholar 

  • Ballongue, J. 1998. Bifidobacteria and probiotic action. In: Lactic Acid Bacteria- Microbiology and Functional Aspects (S. Salminen, A. Von Wright, eds.), 2nd edition, Marcel Dekker, New York, pp. 519–587.

    Google Scholar 

  • Ballongue, J., Schumann, C., Quignon, P. 1997. Effects of lactulose and lactitol on colonic microflora and enzymatic activity. Scand. J. Gastroenterol. 32 Suppl. 222, 41–44.

    CAS  Google Scholar 

  • Beadle, J.R., Saunders, J. P., Wadja Jr., T.J. 1991. Process for manufacturing tagatose, US Patent 5,002,612. March 26, 1991. Assigned to Biospherics Inc.

    Google Scholar 

  • Beadle, J.R., Saunders, J.P., Wadja Jr., T.J. 1992. Process for manufacturing tagatose, US Patent 5,078,796. 7 January 1992. Assigned to Biospherics Inc.

    Google Scholar 

  • Benson, F.R. 1978. Sugar alcohols. In: Kirk-Othmer Encyclopaedia of Chemical Technology (E. Ecteroth, ed.), Vol. 1, 3rd Edition, pp. 754–778, Wiley, New York.

    Google Scholar 

  • Bertelsen, H., Andersen, H., Tvede, M. (2001). Fermentation of D-tagatose by human intestinal bacteria and dairy lactic acid bacteria. Microbial Ecol. Health Dis. 13, 87–95.

    Article  CAS  Google Scholar 

  • Bertelsen, H., Eriknauer, K., Bottcher, K., Christensen, J.S., Stougaard, P., Hansen, O.C., Jorgensen, F. 2006. Process for manufacturing of tagatose. US Patent 6,991,923 B2, issued Jan 31, 2006, assigned to Arla Foods Amba.

    Google Scholar 

  • Bertlesen, H., Jensen, B.B., Buemann, B. 1999. D-tagatose – a novel low-calorie bulk sweetener with prebiotic properties. World Rev. Nutr. Dietetics 85, 98–109.

    Article  Google Scholar 

  • Blum, S., Schiffrin, E. J. 2003. Intestinal microflora and homeostasis of the mucosal immune response: Implications for probiotic bacteria? Curr. Iss. Intest. Microbiol. 4, 53–60.

    CAS  Google Scholar 

  • Boehm, G., Stahl, B. 2003. Oligosaccharides. In: Functional Dairy Products (T. Mattila-Sandholm, M. Saarela, eds.), pp. 203– 243, Woodhead Publishing/CRC Press.

    Google Scholar 

  • Boehm, G., Stahl, B. 2007 Oligosaccharides from milk . J. Nutr., 137, Suppl 847S–849S.

    CAS  Google Scholar 

  • Boehm, G., Stahl, B., Jelinek, J., Knol, J., Miniello, V., Moro, G.E. 2005. Prebiotic carbohydrates in human milk and formulas. Acta Paed. 94 Suppl., 18–21.

    Article  Google Scholar 

  • Bolotin, A., et al. 2004. Complete sequence and comparative genome analysis of the dairy bacterium Streptococcus thermophilus. Nature Biotechnol. 22, 1554–1558.

    Article  CAS  Google Scholar 

  • Bongaerts, G., Severijnen, R., Timmerman, H. 2005. Effect of antibiotics, prebiotics and probiotics in treatment for hepatic encephalopathy. Med. Hypotheses 64, 64–68.

    Article  CAS  Google Scholar 

  • Booy, C.J. 1987. Lactitol – a New Food Ingredient. Bulletin 212, International Dairy Federation, Brussels, pp. 62–68.

    Google Scholar 

  • Bouhnik, Y., Raskine, L., Simoneau, G., Vicaut, E., Neut, C., Flourié, B., Brouns, F., Bornet, F. R. 2004a. The capacity of nondigestible carbohydrates to stimulate fecal bifidobacteria in healthy humans: a double-blind, randomized, placebo-controlled, parallel-group, dose-response relation study. Am. J. Clin. Nutr. 80, 1658–1664.

    CAS  Google Scholar 

  • Bouhnik, Y., Attar, A., Joly, F.A., Riottot, M., Dyard, F., Flourie B. 2004b. Lactulose ingestion increases faecal bifidobacterial counts: a randomised double-blind study in healthy humans. Eur. J. Clin. Nutr. 58, 462–466.

    Article  CAS  Google Scholar 

  • Bourlioux, P., Koletzko, B., Guarner, F., Braesco, V. 2003. The intestine and its microflora are partners for the protection of the host: report on the Danone Symposium “The Intelligent Intestine,” held in Paris, June 14, 2002. Am. J. Clin. Nutr. 78, 675–683.

    Google Scholar 

  • Bovee-Oudenhoven, I.M.J., Termont, D.M.S.L., Heidt, P.J., Van der Meer, R. 1997. Increasing the intestinal resistance of rats to the invasive pathogen Salmonella enteritidis: additive effects of dietary lactulose and calcium. Gut 40, 497–504.

    CAS  Google Scholar 

  • Brighenti, F., Benini, L., Del Rio, D., Casiraghi, C., Pellegrini, N., Scazzina, F., Jenkins, D.J.A., Vantini, I. 2006. Colonic fermentation of indigestible carbohydrates contributes to the second-meal effect. Am. J. Clin. Nutr. 83, 817–822.

    CAS  Google Scholar 

  • Bruzzese, E., Volpicelli, M., Squaglia, M., Tartaglione, A., Guarino, A. 2006. Impact of prebiotics on human health. Digest Liver Dis. 38 Suppl 2, S283–S287.

    Article  Google Scholar 

  • Burvall, A., Asp, N.G., Dahlquist, A. 1979. Oligosaccharide formation during hydrolysis of lactose with Saccharomyces lactis lactase (Maxilact ®) Part 1. Food Chem. 4, 243–250.

    Article  CAS  Google Scholar 

  • Camuesco, D., Peran, L., Comalada, M., Nieto, A., Di Stasi., L.C., Rodriguez-Cabezas, M.E., Concha, A., Zarzuelo, A., Galvez, J. 2005. Preventative effects of lactulose in the trinitrobenzenesulphonic acid model of rat colitis. Inflammatory Bowel Dis. 11, 265–271.

    Article  Google Scholar 

  • Carobbi, R., Bimbi, G., Cipolletti, G. 2001. Process for the preparation of a lactulose syrup by lactose isomerization. US Patent 6,214, 124, issued Aug 10, 2001, assigned to Inalco Spa.

    Google Scholar 

  • Carobbi, R., Miletti, S., Franci, V. 1985. Process for preparing lactulose from lactose, in the form of a syrup or a crystalline product. U.S. Pat. No. 4,536, 221, issued Aug. 20, 1985, assigned to SIRAC Spa.

    Google Scholar 

  • Carubelli, R. 1966. Transformation of disaccharides during borate ion-exchange chromatography. Isomerization of lactose into lactulose. Carbohydr. Res. 2, 480–485.

    Article  CAS  Google Scholar 

  • Challa, A., Rao, D.R., Chawan, C.B., Shackelford, L.1997. Bifidobacterium longum and lactulose suppress azoxymethane-induced colonic aberrant crypt foci in rats. Carcinogenesis 18, 517–521.

    Article  CAS  Google Scholar 

  • Chen, C., Li, L., Wu, Z., Chen, H., Fu, S. 2007. Effects of lactitol on intestinal microflora and plasma endotoxin in patients with chronic viral hepatitis. J. Infect. 54, 98–102.

    Article  Google Scholar 

  • Cho, Y.J., Shin, H.J., Bucke, C. 2003. Purification and biochemical properties of a galactooligosaccharide producing β-galactosidase from Bullera singularis. Biotechnol. Lett. , 25, 2107–2111.

    Article  CAS  Google Scholar 

  • Choi, J.J., Kwon, S.T., Oh, E.J. 2004a. Method for synthesis of galactooligosaccharide using Thermus caldophilus gk24 β-glycosidase and high-level expression system of recombinant Thermus caldophilus gk-24 β-glycosidase used in the same method – plasmid mediated gene transfer and expression in Escherichia coli for recombinant saccharide production. Korean Patent KR 2004033748, issued 28 Apr 2004.

    Google Scholar 

  • Choi, H-J., Kim, C.S., Kim, P., Jung, H-C., Oh, D-K. 2004b. Lactosucrose bioconversion from lactose and sucrose by whole cells of Paenibacillus polymyxa harbouring levansucrase activity. Biotechnol. Prog. 20, 1876–1879.

    Article  CAS  Google Scholar 

  • Chonan, O., Matsumoto, K., Watanuki, M. 1995. Effect of galacto-oligosaccharides on calcium absorption and preventing bone loss in ovariectomized rats. Biosci. Biotechnol. Biochem. 59, 236–239.

    Article  CAS  Google Scholar 

  • Codex Alimentarius. 1998. Food Labelling Complete Texts. FAO/WHO, Rome.

    Google Scholar 

  • Crittenden, R.G. 1999. Prebiotics. In: Probiotics: A Critical Review (G.W. Tannock, ed.), pp. 141– 156, Horizon Scientific Press, Wymondham, UK.

    Google Scholar 

  • Crittenden, R.G., Playne, M.J. 1996. Production, properties and applications of food-grade oligosaccharides. Trends Food Sci. Technol. 7, 353–361.

    Article  CAS  Google Scholar 

  • Crittenden, R.G., Playne, M.J. 2002. Purification of food-grade oligosaccharides using immobilised cells of Zymomonas mobilis. Appl. Microbiol. Biotechnol. 58, 297–302.

    Article  CAS  Google Scholar 

  • Croft-Hill, A. 1898. Reversible zymohydrolysis. J. Chem. Soc. LXIII, 634–658.

    Google Scholar 

  • Crout, D.H.G., Vic, G. 1998. Glycosidases and glycosyl transferases in glycoside and oligosaccharide synthesis. Curr. Opinion Chem. Biol. 2, 98–111.

    Article  CAS  Google Scholar 

  • Cummings, J.H., Macfarlane, G.T., Macfarlane, S. 2003. Intestinal bacteria and ulcerative colitis. Curr. Iss. Intest. Microbiol. 4, 9–20.

    CAS  Google Scholar 

  • Dbouk, N., McGuire, B.M. 2006. Hepatic encephalopathy: a review of its pathophysiology and treatment. Curr. Treatment Options Gastroenterol. 9, 464–474.

    Article  Google Scholar 

  • De Preter, V., Geboes, K., Verbrugghe, K., De Vuyst, L., Vanhoutte, T., Huys, G., Swings, J., Pot, B., Verbeke, K. 2004. The in vivo use of the stable isotope-labelled biomarkers lactose-[N-15]ureide and [H-2(4)]tyrosine to assess the effects of pro- and prebiotics on the intestinal flora of healthy human volunteers. Br. J. Nutr. 92, 439–446.

    Article  CAS  Google Scholar 

  • De Preter, V., Vanhoutte, T., Huys, G., Swings, J., Rutgeerts, P., Verbeke, K. 2006. Effect of lactulose and Saccharomyces boulardii administration on the colonic urea-nitrogen metabolism and the bifidobacteria concentration in healthy human subjects. Alimentary Pharmacol. Therapeutics 23, 963–974.

    Article  CAS  Google Scholar 

  • De Slegte, J., et al. 2002. Determination of trans-galactooligosaccharides in selected food products by ion-exchange chromatography: collaborative study. J. Ass. Off. Anal. Chem. Internat. 85, 417–423.

    Google Scholar 

  • Dombou, M., Tomioka, I., Tsurutani, R., Kitabatake, S., Nakajima, H. 1994. Method for production of a growth factor for Bifidobacterium sp. US Patent 5,294, 546, issued 15 March 1994, assigned to Unitika Ltd, Japan.

    Google Scholar 

  • Dorscheid, R.E., Krumbholz, M.J. 1991. Method of manufacturing lactulose. US Patent 5,071, 530, issued 10 Dec 1991, assigned to Duphar International Research B.V.

    Google Scholar 

  • Edwards, C.A., Parrett, A.M. 2002. Intestinal flora during the first months of life: new perspectives. Br. J. Nutr. 88(Suppl 1), S11–S18.

    Article  CAS  Google Scholar 

  • Fanaro, S., Boehm, G., Garssen, J., Knol, J., Mosca, F., Stahl, B., Vigi, V. 2005. Galacto-oligosaccharides and long-chain fructo-oligosaccharides as prebiotics in infant formulas: a review. Acta Paediatrica 94, 22–26.

    Article  Google Scholar 

  • Favier, C., Neut, C., Mizon, C., Cortot, A., Colombel, J.F., Mizon, J. 1997. Fecal beta-D-galactosidase production and bifidobacteria are decreased in Crohn's disease. Digestive Dis. Sci. 42, 817–822.

    Article  CAS  Google Scholar 

  • Ferchaud-Roucher, V., Pouteau, E., Piloquet, H., Zaïr, Y., Krempf, M. 2005. Colonic fermentation from lactulose inhibits lipolysis in overweight subjects. Am. J. Physiol. 289, E716–E720.

    CAS  Google Scholar 

  • Fernández-Bañares, F. 2006. Nutritional care of the patient with constipation. Clin. Gastroenterol. 20, 575–587.

    Google Scholar 

  • Finkelman, M.A.J. 1989. Yeast strain development for extracellular enzyme production. In: Yeast Strain Selection (C.J. Panchal, ed.), pp. 185– 223, Marcel Dekker Inc., New York.

    Google Scholar 

  • Fu, W., Song, K. 1993. Removal of boric acid catalyst in lactose isomerization. Chinese Patent CN 1,073,668.

    Google Scholar 

  • Fujimori, I. 1992. Pet food, US Patent 5,294, 458, issued Mar 15, 1994, assigned to Maruha Corporation and Ensuiko Sugar Refining Co., Ltd., Japan.

    Google Scholar 

  • Fujita K., Hara K., Hashimoto H., Kitahata S. 1990a. Purification and some properties of β-fructofuranosidase I from Arthrobacter sp. K-1. Agric. Biol. Chem. 54, 913–919.

    Article  CAS  Google Scholar 

  • Fujita, K., Hara, K., Hashimoto, H., Kitahata, S. 1990b. Transfructosylation catalyzed by β-fructofuranosidase I from Arthrobacter sp. K-1 Agric. Biol. Chem. 54, 2655–2661.

    Article  CAS  Google Scholar 

  • Fujita, K., Hara, K., Hashimoto, H., Kitahata, S. 1992a. Method for the preparation of fructose-containing oligosaccharide US Patent 5,089, 401, issued Feb 18, 1992, assigned to Ensuiko Sugar Refining Co Ltd., Japan.

    Google Scholar 

  • Fujita K, Kitahata S, Hara, K., Hashimoto, H. 1992b. Production of lactosucrose and its properties. In: Carbohydrates in Industrial Synthesis (M.A. Clarke, ed.), pp. 68– 76, Proc. Symp. Div. Carbohyd. Chem. Amer. Chem. Soc., Bartens, Berlin.

    Google Scholar 

  • Fujita, K., Hara, K., Sakai, S., Miyake, T., Yamashita, M., Tsunstomi, Y., Mitsuoka, Y. 1991. Effects of 4-β-D-galactosylsucrose (lactosucrose) on intestinal flora and its digestibility in humans. J. Jap. Soc. Starch Sci. 38, 249–255.

    Article  CAS  Google Scholar 

  • Garman, J., Coolbear, T., Smart, J.B. 1996. The effect of cations on the hydrolysis of lactose and the transferase reactions catalysed by β-galactosidase from six strains of lactic acid bacteria. Appl. Microbiol. Biotechnol. 46, 22–27.

    Article  CAS  Google Scholar 

  • German Culture Collection. 2007. www.dsmz.de/, accessed October 15, 2007.

  • Gibson, G.R., McCartney, A.L., Rastall, R.A. 2005. Prebiotics and resistance to gastrointestinal infections. Br. J. Nutr. 93, 31–34.

    Article  CAS  Google Scholar 

  • Gibson, G. R., Probert, H. M., Van Loo, J.A.E., Roberfroid, M.B. 2004. Dietary modulation of the human colonic microflora: updating the concept of prebiotics. Nutr. Res. Rev. 17, 257–259.

    Article  CAS  Google Scholar 

  • Gibson, G.R., Roberfroid, M.B. 1995. Dietary modulation of the human colonic microbiota – introducing the concept of prebiotics. J.Nutr. 125, 1401–1412.

    CAS  Google Scholar 

  • Gorin, P.A., Spencer, J.F.T., Phaff, H.J. 1964. The structures of galactosyl-lactose and galactobiosyl-lactose produced from lactose by Sporobolomyces singularis. Can. J. Chem. 42, 1341–1344.

    Article  CAS  Google Scholar 

  • Greenberg, N.A., Mahoney, R.R. 1982. Production and characterization of β-galactosidase from Streptococcus thermophilus. J. Food Sci. 47, 1824–1828, 1835.

    Article  CAS  Google Scholar 

  • Greenberg, N.A., Mahoney, R.R. 1983. Formation of oligosaccharides by β-galactosidase from Streptococcus thermophilus. Food Chem. 10, 195–204.

    Article  CAS  Google Scholar 

  • Griffiths, M.W., Muir, D.D. 1978. Properties of a thermostable β-galactosidase from a thermophilic Bacillus: Comparison of the enzyme activity of whole cells, purified enzyme and immobilized whole cells. J. Sci. Food Agric. 29, 753–761.

    Article  CAS  Google Scholar 

  • Grogan, D.W. (1991). Evidence that β-galactosidase of Sulfobus solfataricus is only one of several activities of a thermostable β-D-glucosidase. Appl. Environ. Microbiol. 57, 1644–1649.

    CAS  Google Scholar 

  • Guarner, F., Malagelada, J.R. 2003. Gut flora in health and disease. Lancet 361, 512–519.

    Article  Google Scholar 

  • Guth, J.H., Tumerman, L. 1970. Method of making lactulose. US Patent 3,546,206. Dec. 8, 1970, assigned to Kraftco Corp.

    Google Scholar 

  • Gyorgy, P., Norris, R.F., Rose, C.S. 1954a. Bifidus factor I. A variant of Lactobacillus bifidus requiring a special growth factor. Arch. Biochem. Biophys. 48, 193–201.

    Article  CAS  Google Scholar 

  • Gyorgy, P., Kuhn, R., Rose, C.S., Zilliken, F. 1954b. Bifidus factor II. Its occurrence in milk from different species and in other natural products. Arch. Biochem. Biophys. 48, 202–208.

    Article  CAS  Google Scholar 

  • Haarman, M., Knol, J. 2005. Quantitative real-time PCR assays to identify and quantify fecal Bifidobacterium species in infants receiving a prebiotic infant formula. Appl. Environ. Microbiol. 71, 2318–2324.

    Article  CAS  Google Scholar 

  • Haarman, M., Knol, J. 2006. Quantitative real-time PCR analysis of fecal Lactobacillus species in infants receiving a prebiotic infant formula. Appl. Environ. Microbiol. 72, 2359–2365.

    Article  CAS  Google Scholar 

  • Hansen, O.C., Jorgensen, F., Stougaard, P., Bertelsen, H., Bottcher, K., Christensen, H.J.S., Eriknauer, K. 2006. Thermostable isomerase and use hereof, in particular for producing tagatose. US Patent 7,052, 898, issued 30 May 2006, assigned to Bioneer A/S.

    Google Scholar 

  • Hara, K., Fujita, K., Yamashita, M., Tsunetomi, Y., Sakai, S., Miyake, T. 1992. Process for preparing lactosucrose high-content powder. US Patent 5,130, 239, issued July 14, 1992, assigned to KK Hayashibara SKK, and Ensuiko SKK.

    Google Scholar 

  • Hara, K., Fujita, K., Yamashita, M., Tsunetomi, Y., Sakai, S., Miyake, T. 1994a. Process for preparing a powder having a high concentration of lactosucrose and use of said powder. US Patent 5,296, 473, March 22, 1994, assigned to KK Hayashibara SKK.

    Google Scholar 

  • Hara, H., Li, S.-T., Sasaki, M., Maruyama, T., Terada, A., Ogata, Y., Fujita, K., Ishigami, H., Hara, K., Fujimori, I., Mitsuoka, T. 1994b. Effective dose of lactosucrose on fecal flora and fecal metabolites of humans. Bifidobacteria Microfl. 13, 51–63.

    Google Scholar 

  • Hardy, M.R., Townsend, R.R. 1988. Separation of positional isomers of oligosaccharides and glycopeptides by high-performance anion-exchange chromatography with pulsed amperometric detection. Proc. Natl. Acad. Sci., USA 85, 3289–3293.

    Article  CAS  Google Scholar 

  • Harmsen, H.J.M., Wildeboer-Veloo, A.C.M., Raangs, C.G., Wagendorp, A.A., Klijn, N., Bindels, J.G., Welling, G.W. 2000. Analysis of intestinal flora development in breast-fed and formula-fed infants by using molecular identification and detection methods. J. Pediatr. Gastroenterol. Nutr. 30, 61–67.

    Article  CAS  Google Scholar 

  • Heavey, P.M., Savage, S.A., Parrett, A., Cecchini, C., Edwards, C.A., Rowland, I.R. 2003. Protein-degradation products and bacterial enzyme activities in faeces of breast-fed and formula-fed infants. Br. J. Nutr. 89, 509–515.

    Article  CAS  Google Scholar 

  • Hicks, K.B. 1981. Ketose sugars from aldose sugars. U.S. Pat. No. 4,273, 922, issued Jun. 16, 1981, assigned to USA.

    Google Scholar 

  • Hicks, K.B., Parrish, F.W. 1980. A new method for the preparation of lactulose from lactose. Carbohydr. Res. 82, 393–397.

    Article  CAS  Google Scholar 

  • Hicks, K.B., Simpson, G.L., Bradbury, A.G.W. 1986. Removal of boric acid and related compounds from solutions of carbohydrates with boron-selective resin (IRA-743). Carbohydr. Res. 147, 39–48.

    Article  CAS  Google Scholar 

  • Holma, R., Juvonen, P., Asmawi, M.Z., Vapaatalo, H., Korpela, R. 2002. Galacto-oligosaccharides stimulate the growth of bifidobacteria but fail to attenuate inflammation in experimental colitis in rats. Scand. J. Gastroenterol. 37, 1042–1047.

    Article  CAS  Google Scholar 

  • Inchem. 2008. International Programme on Chemical Safety (IPCS) and the Canadian Centre for Occupational Health and Safety (CCOHS) website IPCS INCHEM. www.inchem.org/pages/jecfa.html accessed 17 April 2008.

  • IFST. 2007. Information Statement on Dietary Fibre. (Institute of Food Science & Technology Trust Fund, London, U.K.) 10 pages. www.ifst.org/, accessed 5 June 2007.

  • IDF. 1995. Provisional Standard. Milk. Determination of lactulose content. Enzymatic method. International Dairy Federation, Brussels, Standard 175.

    Google Scholar 

  • Ipatiew, W. 1912. Katalytische Reaktionen bei hohen Temperaturen und Drucken. XXV Berichte der Deutschen Chemischen Gesselschaft. 45, 3218–3226 [in German].

    Article  Google Scholar 

  • Ishikawa, E., Sakai, T., Ikemura, H., Matsumoto, K., Abe, H. 2005. Identification, cloning, and characterization of a Sporobolomyces singularis β-galactosidase-like enzyme involved in galacto-oligosaccharide production. J. Biosci.Bioeng. 99, 331–339.

    Article  CAS  Google Scholar 

  • IUPAC. 1996. Nomenclature of carbohydrates. Pure Appl. Chem. 68, 1919–2008.

    Article  Google Scholar 

  • Izume, M., Nagae, S., Kawagishi, H., Ohtakara, A. 1992. Preparation of N-acetylchitooligosaccharides from enzymatic hydrolyzates of chitosan. Biosci. Biotech. Biochem. 56, 1327–1328.

    Article  CAS  Google Scholar 

  • JECFA. 2008. Joint FAO/WHO Expert Committee on Food Additives. www.who.int/ipcs/food/jecfa/en/, accessed 17 April 2008.

  • Ji, E.S., Park, N.H., Oh, D.K. 2005. Galacto-oligosaccharide production by a thermostable recombinant β-galactosidase from Thermotoga maritima – Thermotaga maritima recombinant thermostable β-galactosidase production for galacto-oligosaccharide preparation. World J. Microbiol. Biotechnol. 21, 759–764.

    Article  CAS  Google Scholar 

  • Johansson, E., Hedbys, L., Mosbach, K., Larsson, P.-O. 1989. Studies of the reversed-mannosidase reaction in high concentrations of mannose. Enz. Microbial. Technol. 11, 347–352.

    Article  CAS  Google Scholar 

  • Jorgensen, F., Hansen, O.C., Stougaard, P. 2001. High efficiency synthesis of oligosaccharides with a truncated β-galactosidase from Bifidobacterium bifidum. Appl. Microbiol. Biotechnol. 57, 647–652.

    Article  CAS  Google Scholar 

  • Jouët, P., Sabate, J.-M., Cuillerier, E., Coffin, B., Lemann, M., Jian, R., Flourie, B. 2006. Low-dose lactulose produces a tonic contraction in the human colon. Neurogastroenterol. Motility 18, 45–52.

    Article  Google Scholar 

  • Juśkiewicz, J., Klewicki, R., Zdunczyk, Z. 2006. Consumption of galactosyl derivatives of polyols beneficially affects cecal fermentation and serum parameters in rats. Nutr. Res. 26, 531–536.

    Article  CAS  Google Scholar 

  • Kawakami, K., Makino, I., Asahara, T., Kato, I., Onoue, M. 2005. Dietary galacto-oligosaccharides mixture can suppress serum phenol and p-cresol levels in rats fed tyrosine diet. J. Nutr. Sci. Vitaminol. 51, 182–186.

    Article  CAS  Google Scholar 

  • Kawase, M., Pilgrim, A., Araki, T., Hashimoto, K. 2001. Lactosucrose production using a simulated moving bed reactor. Chem. Eng. Sci. 56, 453–458.

    Article  CAS  Google Scholar 

  • Kim, P. 2004. Current studies on biological tagatose production using L-arabinose isomerase: A review and future prospects. Appl. Microbiol. Biotechnol. 65, 243–249.

    CAS  Google Scholar 

  • Kirjavainen, P.V., Reid, G. 2006. The infant intestinal microbiota in allergy. In: Gastrointestinal Microbiology (A.C. Ouwehand, E. E. Vaughan, eds.), pp. 189– 205, Taylor and Francis, New York.

    Google Scholar 

  • Knol, J., Boehm, G., Lidestri, M., Negretti, F., Jelinek, J., Agosti, M., Stahl, B., Marini, A., Mosca, F. 2005. Increase of faecal bifidobacteria due to dietary oligosaccharides induces a reduction of clinically relevant pathogen germs in the faeces of formula-fed preterm infants. Acta Paed. 94, 31–33.

    Article  Google Scholar 

  • Kobata, A. 1996. Glycobiology. In: Encyclopaedia of Molecular Biology and Molecular Medicine (R.A. Meyers, ed.), Volume 2, pp. 446– 457, VCH, Weinheim, Germany.

    Google Scholar 

  • Kobayashi, Y., Kan, T., Terashima, T. 1990. Method for producing processed milk containing galactooligosaccharide. U.S. Patent 4944952. issued 31 July 1990; assigned to K.K. Yakult Honsha.

    Google Scholar 

  • Koizumi, S., Endo, T., Tabata, K., Ozaki, A. 1998. Large-scale production of UDP-galactose and globotiose by coupling metabolically engineered bacteria. Nature Biotechnol. 16, 847–850.

    Article  CAS  Google Scholar 

  • Kozempel, M.F., Kurantz, M.J. 1994. The isomerization kinetics of lactose to lactulose in the presence of borate. J. Chem. Tech. Biotechnol. 59, 25–29.

    Article  CAS  Google Scholar 

  • Kummel, K.F., Brokx, S. 2001. Lactitol as a functional prebiotic. Cereal Foods World 46, 424–429.

    CAS  Google Scholar 

  • Kunz, C., Rudloff, S. 1996. Strukturelle und funktionelle aspekte von oligosacchariden in frauenmilch. Z. Ernahrungswiss. 35, 22–31.

    Article  CAS  Google Scholar 

  • Kunz, C., Rudloff, S. 2002. Health Benefits of Milk-Derived Carbohydrates. Bulletin 375, International Dairy Federation, Brussels, pp. 72–79.

    Google Scholar 

  • Kunz, C., Rudloff, S., Baier, W., Klein, N., Strobel, S. 2000. Oligosaccharides in human milk: structural, functional, and metabolic aspects. Ann. Rev. Nutr. 20, 699–722.

    Article  CAS  Google Scholar 

  • Laerke, H.N., Jensen, B.B. 1999. D-Tagatose has low small intestinal digestibility but high large intestinal fermentability in pigs. J. Nutr. 129, 1002–1009.

    CAS  Google Scholar 

  • Laerke, H.N., Jensen, B.B., Hojsgaard, S. 2000. In vitro fermentation pattern of D-tagatose is affected by adaptation of the microbiota from the gastrointestinal tract of pigs. J. Nutr. 130, 1772–1779.

    CAS  Google Scholar 

  • LFRA. 2000. Ingredients Handbook: Prebiotics and probiotics (G. Gibson, F. Angus, eds.), Leatherhead Food Research Association Ltd., Surrey, UK.

    Google Scholar 

  • Lee, Y.C. (1990). High performance anion-exchange chromatography for carbohydrate analysis. Anal. Biochem. 189, 151–162.

    Article  CAS  Google Scholar 

  • Lee, Y-J., Kim, C.S., Oh, D-K. 2004. Lactulose production by β-galactosidase in permeabilized cells of Kluyveromyces lactis. Appl. Microbiol. Biotechnol. 64, 787–793.

    Article  CAS  Google Scholar 

  • Lemoine, J., Chirat, F., Wieruszeski, J.-M, Strecker, G., Favre, N., Neeser, J.-R. 1997. Structural characterization of the exocellular polysaccharides produced by Streptococcus thermophilus SFi39 and SFi12. Appl. Environ. Microbiol., 63, 3512–3518.

    CAS  Google Scholar 

  • Linko, S., Enwald, S., Vahvaselka, M., Mayra-Makinen, A. 1992. Optimization of the production of β-galactosidase by an autolytic strain of Streptococcus salivarius subsp. thermophilus. Ann. New York Acad. Sci. 672, 588–594.

    Article  CAS  Google Scholar 

  • Linskens, R.K., Huijsdens, X.W., Savelkoul, P.H.M., Vandenbroucke-Grauls, C.M.J.E., Meuwissen, S.M.G. 2001. The bacterial flora in inflammatory bowel disease: Current insights in pathogenesis and the influence of antibiotics and probiotics. Scand. J. Gastroenterol. 36, S29–S40.

    Article  Google Scholar 

  • Ludwig, R., Ozga, M., Zamocky, M., Peterbauer, C., Kulbe, K.D., Haltrich, D. 2004. Continuous enzymatic regeneration of electron acceptors used by flavoenzymes: Cellobiose dehydrogenase-catalyzed production of lactobionic acid as an example. Biocatal. Biotransform. 22, 97–104.

    Article  CAS  Google Scholar 

  • Macfarlane, S., Macfarlane, G.T., Cummings, J.H. 2006. Review article: prebiotics in the gastrointestinal tract. Aliment. Pharmacol. Therapeut. 24, 701–714.

    Article  CAS  Google Scholar 

  • Mahoney, R.R. 1997. Lactose: enzymatic modification. In: Advanced Dairy Chemistry (P.F. Fox, ed.), 2nd Edition, Vol. 3, pp. 77–125, Chapman & Hall, London.

    Google Scholar 

  • Mahoney, R.R., Whitaker, J.R. 1978. Purification and physico-chemical properties of β-galactosidase from Kluyveromyces fragilis. J. Food Sci. 43, 584–591.

    Article  CAS  Google Scholar 

  • Mahoney, R.R., Nickerson, T.A., Whitaker, J.R. 1975. Selection of strain, growth conditions, and extraction procedures for optimum production of lactase from Kluyveromyces fragilis. J. Dairy Sci. 58, 1620–1629.

    Article  CAS  Google Scholar 

  • Marteau, P., Seksik, P., Shanahan, F. 2003. Manipulation of the bacterial flora in inflammatory bowel disease. Best Practice Res: Clin. Gastroenterol. 17, 47–61.

    Article  CAS  Google Scholar 

  • Matsumoto, K., Kobayashi, Y., Ueyama, S., Watanabe, T., Tanaka, R., Kan, T., Kuroda, A., Sumihara, Y. 1993. Galactooligosaccharides. In: Oligosaccharides. Production, Properties, and Applications (T. Nakakuki, ed.), Japanese Technology Reviews Vol 3, No. 2, pp. 90–106, Gordon and Breach, Science Publishers, Basel.

    Google Scholar 

  • McCartney A.L., Gibson, G.R. 2006. The normal microbiota of the human gastrointestinal tract: history of analysis, succession, and dietary influences. In: Gastrointestinal Microbiology (A.C. Ouwehand, E.E. Vaughan, eds.), pp. 51–73, Taylor and Francis, New York.

    Google Scholar 

  • Mendicino, J. F. (1960). Effect of borate on the alkali-catalyzed isomerisation of sugars. J. Am. Chem. Soc., 82, 4975–4979.

    Article  CAS  Google Scholar 

  • Mesters, P.H.J., Brokx, S. 2000. Lactitol: a functional prebiotic. Functional Foods 2000 Conference Proceedings, The Hague, The Netherlands (F. Angus, C. Miller, eds.), pp. 173–189, Leatherhead Publishing, UK.

    Google Scholar 

  • Meyer, D., Tungland, B. 2001. Non-digestible oligosaccharides: their physiological effects and health implications. In: Advanced Dietary Fibre Technology (B.V. McCleary, L. Prosky, eds.), pp. 455– 470, Blackwell Publishing, Oxford, UK.

    Google Scholar 

  • Minami,Y., Yazawa, K., Tamura, Z., Tanaka, T., Yamamoto, T. 1983. Selectivity of utilization of galactosyl-oligosaccharides by bifidobacteria. Chem. Pharm. Bull. 31, 1688–1691.

    Article  CAS  Google Scholar 

  • Miyamoto, Y., Ooi, T., Kinoshita, S. 2000. Production of lactobionic acid from whey by Pseudomonas sp. LS13-1. Biotechnol. Lett. 22, 427–430.

    Article  CAS  Google Scholar 

  • Mizota, T., Tamura, Y., Tomita, M., Okonogi, S. 1987. Lactulose as a Sugar with Physiological Significance. Bulletin 212, International Dairy Federation, Brussels, pp. 69–76.

    Google Scholar 

  • Mizota, T. 1996. Lactulose as a growth promoting factor for Bifidobacterium and its physiological aspects. Bulletin 313, International Dairy Federation, Brussels, pp. 43–48.

    Google Scholar 

  • Modler, H.W., McKellar, R.C., Yaguchi, M. 1990. Bifidobacteria and bifidogenic factors. Can. Inst. Food Sci. Technol. 23, 29–41.

    CAS  Google Scholar 

  • Montgomery, E.M., Hudson, C.S. 1930. Relations between rotatory power and structure in the sugar group. XXVII. Synthesis of a new disaccharide ketose (lactulose) from lactose. J. Am. Chem. Soc. 52, 2101–2106.

    Article  CAS  Google Scholar 

  • Morohashi, T. 2002. The effect on bone of stimulated intestinal mineral absorption following fructooligosaccharide consumption in rats. Biosci. Microfl. 21, 21–25.

    CAS  Google Scholar 

  • Mountzouris, K.C., McCartney, A.L., Gibson, G.R. 2002. Intestinal microflora of human infants and current trends for its nutritional modulation. Br. J. Nutr. 87, 405–420.

    CAS  Google Scholar 

  • Mozaffar, Z., Nakanishi, K., Matsuno, R., Kamikubo, T. 1984. Purification and properties of β-galactosidase from Bacillus circulans. Agric. Biol. Chem. 48, 3053–3061.

    Article  CAS  Google Scholar 

  • Mwenya, B., Santoso, B., Sar, C., Gamo, Y., Kobayashi, T., Arai, I., Takahashi, J. 2004a. Effects of including β1-4 galacto-oligosaccharides, lactic acid bacteria or yeast culture on methanogenesis as well as energy and nitrogen metabolism in sheep. Anim. Feed Sci. Technol. 115, 313–326.

    Article  CAS  Google Scholar 

  • Mwenya, B., Zhou, X., Santoso, B., Sar, C., Gamo, Y., Kobayashi, T., Takahashi, J. 2004b. Effects of probiotic-vitacogen and β1-4 galacto-oligosaccharides supplementation on methanogenesis and energy and nitrogen utilization in dairy cows. Asian-Austral. J. Anim. Sci. 17, 349–354.

    CAS  Google Scholar 

  • Nagendra, R., Rao, S.V. 1992. An improved colorimetric method for the estimation of lactulose in lactose-lactulose mixtures. Food. Chem. 43, 399–402.

    Article  CAS  Google Scholar 

  • Nakakuki, T. 2002. Present status and future of functional oligosaccharide development in Japan. Pure Appl. Chem. 74, 1245–1251.

    Article  CAS  Google Scholar 

  • Nakanishi, K., Matsuno, R., Torii, K., Yamamoto, K., Kamikubo, T. 1983. Properties of immobilized β-galactosidase from Bacillus circulans. Enz. Microb. Technol. 5, 115–120.

    Article  CAS  Google Scholar 

  • Nakao, M., Harada, M., Kodama, Y., Nakayama, T., Shibano, Y., Amachi, T. 1994. Purification and characterization of a thermostable β-galactosidase with high transgalactosylation activity from Saccharopolyspora rectivirgula. Appl. Microb. Biotechnol. 40, 657–663.

    Article  CAS  Google Scholar 

  • Nakayama, T., Kodama, Y., Amano, N., Nakao, M., Shibano, Y., Amachi, T. 1992. Heat-resistant β-galactosyltransferase, its production process and its use. United States Patent 5153128. issued 10 June 1992; assigned to Suntory ltd., Osaka, Japan.

    Google Scholar 

  • Nakayama, T., Kodama, Y., Amano, N., Nakao, M., Shibano, Y., Amachi, T. 1993. Process for producing novel heat-resistant β-galactosyltransferase. U.S.Patent 5,234,828, issued 10 Aug 1993; assigned to Suntory Ltd, Osaka, Japan.

    Google Scholar 

  • NCBI. 2007. National Center for Biological Information, US National Library of Medicine, USA, Taxonomy browser (www.ncbi.nlm.nih.gov), accessed 13 August 2007.

  • Nilsson, K.G.I. 1988. Enzymatic synthesis of oligosaccharides. Trends Biotechnol. 6, 256–264.

    Article  CAS  Google Scholar 

  • Normen, L., Laerke, H. N., Jensen, B.B., Langkilde, A.M., Andersson, H. 2001. Small-bowel absorption of D-tagatose and related effects on carbohydrate digestibility: an ileostomy study. Am. J. Clin. Nutr. 73, 105–110.

    CAS  Google Scholar 

  • Ohkusa, T., Ozaki,Y., Sato, C., Mikuni, K., Ikeda, H. 1995. Long-term ingestion of lactosucrose increases Bifidobacterium sp. in human fecal flora. Digestion 56, 415–420.

    Article  CAS  Google Scholar 

  • Ohtsuka, K., Oki, S., Owaza, O., Uchida, T. 1992. [Isolation and cultural conditions of galactooligosaccharide producing yeast Cryptococcus laurentii]. Hakkokogaku Kaishi 66, 225–233.

    Google Scholar 

  • Ohtsuka, K., Tanoh, A., Ozawa, O., Kanematsu, T., Uchida, T., Shinke, R. 1990. Purification and properties of a β-galactosidase with high galactosyl transfer activity from Cryptococcus laurentii. J. Ferment. Bioeng. 70, 301–307.

    Article  CAS  Google Scholar 

  • Onishi, N., Kira, I., Yokozeki, K. 1996. Galacto-oligosaccharide production from lactose by Sirobasidium magnum CBS6803. Lett. Appl. Microbiol. 23, 253–256.

    Article  CAS  Google Scholar 

  • Onishi, N., Tanaka, T. 1995. Purification and properties of a novel thermostable galacto-oligosaccharide-producing β-galactosidase from Sterigmatomyces elviae CBS 8119. Appl. Environ. Microbiol. 61, 4026–4030.

    CAS  Google Scholar 

  • Onishi, N., Tanaka, T. 1996. Purification and properties of a galacto- and gluco-oligosaccharide-producing β-glycosidase from Rhodotorula minuta IFO879. J. Ferment. Bioeng. 82, 439–443.

    Article  CAS  Google Scholar 

  • Onishi, N., Tanaka, T. 1997. Purification and characterization of galacto-oligosaccharide producing β-galactosidase from Sirobasidium magnum. Lett. Appl. Microbiol. 24, 82–86.

    Article  CAS  Google Scholar 

  • Onishi, N., Yamashiro, A., Yokozeki, K. 1995. Production of galacto-oligosaccharide from lactose by Sterigmatomyces elviae CBS 8119. Appl. Environ. Microbiol. 61, 4022–4025.

    CAS  Google Scholar 

  • Onishi, N., Yokozeki, K. 1992. Method for producing galactose transfer products. US Patent 5149640; issued Sept 22, 1992, assigned to Ajinomoto Co., Inc.

    Google Scholar 

  • Özaslan, C., Türkçapar, A.G., Kesenci, M., Karayalçin, K., Yerdel, M.A., Bengisun, S., Törüner, A. 1997. Effect of lactulose on bacterial translocation. Eur. J. Surg. 163, 463–467.

    Google Scholar 

  • Ozawa,O., Ohtsuka, K., Uchida, T., Usami, S. 1991. 4′-Galactosyl lactose production in a jar fermentor by Cryptococcus laurentii OKN-4. J. Ferm. Bioeng. 72, 309–310.

    Article  CAS  Google Scholar 

  • Park, N.-H., Choi, H.-J., Oh, D.-K. 2005. Lactosucrose production by various microorganisms harbouring levansucrase activity. Biotechnol. Lett. 27, 495–497.

    Article  CAS  Google Scholar 

  • Parrish, F.W. 1970. Isomerization of glucose, maltose and lactose with amino compounds. US Patent 3,514,327. May 26, 1970, assigned to US Army.

    Google Scholar 

  • Pazur, J.H. 1970. Oligosaccharides. In: The Carbohydrates: Chemistry and Biochemistry (W. Pigman, D. Horton, A. Herp, eds.), pp. 69–137, Vol. IIA, 2nd edition, Academic Press, New York.

    Google Scholar 

  • Pazur, J.H. 1953. The enzymatic conversion of lactose into galactosyl oligosaccharides. Science 117, 355–356.

    Article  CAS  Google Scholar 

  • Pazur, J.H. 1954. The mechanism of enzymatic synthesis of galactosyl oligosaccharides. J. Biol. Chem. 208, 439–444.

    CAS  Google Scholar 

  • Pazur, J.H., Tipton, C.L., Budovich, T., Marsh, J.M. 1958. Structural characterization of products of enzymatic disproportionation of lactose. J. Am. Chem. Soc. 80, 119–121.

    Article  CAS  Google Scholar 

  • Petuely, F. 1957. Bifidusflora bei flaschenkindern durch bifidogene substanzen (Bifidusfaktor). Z. Kinderheilkunde 79, 174–179.

    Article  CAS  Google Scholar 

  • Petzelbauer, I., Nidetzky, B., Haltrich, D., Kulbe, K.D. 1999. Development of an ultra high temperature process for the enzymatic hydrolysis of lactose. I. The properties of two thermostable β-glycosidases. Biotechnol. Bioeng. 64, 322–332.

    Article  CAS  Google Scholar 

  • Petzelbauer I., Zeleny, R., Reiter, A., Kulbe, K.D., Nidetzky, B. 2000. Development of an ultra high temperature process for the enzymatic hydrolysis of lactose. II. Oligosaccharide formation by two thermostable β-glycosidases. Biotechnol. Bioeng. 69, 140–149.

    Article  CAS  Google Scholar 

  • Petzelbauer, I., Splechtna, B., Nidetzky, B. 2002a. Development of an ultra high temperature process for the enzymatic hydrolysis of lactose. III. Utilization of two thermostable β-glycosidases in a continuous ultrafiltration membrane reactor and galacto-oligosaccharide formation under steady-state conditions. Biotechnol. Bioeng. 77, 394–404.

    Article  CAS  Google Scholar 

  • Petzelbauer, I., Kuhn, B., Splechtna, B., Kulbe, K.D., Nidetzky, B. 2002b. Development of an ultra high temperature process for the enzymatic hydrolysis of lactose. IV. Immobilization of two thermostable β-glycosidases and optimization of a packed-bed reactor for lactose conversion. Biotechnol. Bioeng. 77, 619–631.

    Article  CAS  Google Scholar 

  • Pilgrim, A., Kawase, M., Ohashi, M., Fujita, K., Murakami, K., Hashimoto, K. 2001. Reaction kinetics and modeling of the enzyme-catalyzed production of lactosucrose using β-fructofuranosidase from Arthrobacter sp. K-1. Biosci. Biotechnol. Biochem. 65, 758–765.

    Article  CAS  Google Scholar 

  • Pisani, F. M., Rella, R., Raia, C., Rozzo, C., Nucci, R., Gambacotra, A., DeRosa, M., Rossi, M. 1990. Thermostable β-galactosidase from the archaebacterium Sulfolobus solfataricus: purification and properties. Eur. J. Biochem. 187, 321–328.

    Article  CAS  Google Scholar 

  • Playne, M.J., Morel, B., Dimopoulos, A. 1993. Production of carbohydrate-based functional foods using enzyme and fermentation technologies. Proc. 11th Australian Biotechnol. Conf., Perth, pp. 207–209.

    Google Scholar 

  • Playne, M.J., Crittenden, R. 1996. Commercially-available Oligosaccharides. Bulletin 313, International Dairy Federation, Brussels. pp.10–22.

    Google Scholar 

  • Playne, M.J. 2002a. Galacto-oligosaccharides. In: Encyclopaedia of Dairy Sciences (H. Roginski, J.W. Fuquay, P.F. Fox eds.), pp. 1151–1158, Academic Press, San Diego, CA, USA.

    Google Scholar 

  • Playne, M.J. 2002b. Glycoscience: oligosaccharides as drugs, functional foods, and receptors in the gut. Australas. Biotechnol. 12, 35–37.

    Google Scholar 

  • Ponz de Leon, M., Roncucci, L. 1997. Chemoprevention of colorectal tumours: role of lactulose and of other agents. Scand. J. Gastroenterol. 32 Suppl. 222, 72–75.

    Google Scholar 

  • Prasad, S., Dhiman, R.K., Duseja, A., Chawla, Y.K., Sharma, A., Agarwal, R. 2007. Lactulose improves cognitive functions and health-related quality of life in patients with cirrhosis who have minimal hepatic encephalopathy. Hepatology 45, 549–559.

    Article  Google Scholar 

  • Prenosil, J.E., Stucker, E., Bourne, J.R. 1987a. Formation of oligosaccharides during enzymatic lactose: Part 1: State of art. Biotechnol. Bioeng. 30,1019–1025.

    Article  CAS  Google Scholar 

  • Prenosil, J.E., Stucker, E., Bourne, J.R. 1987b. Formation of oligosaccharides during enzymatic lactose hydrolysis and their importance in a whey hydrolysis process: Part II: Experimental. Biotechnol. Bioeng. 30, 1026–1031.

    Article  CAS  Google Scholar 

  • Pyun, Y.R., Kim, B.C., Lee, H.S., Lee, D.W., Lee, Y.H. 2005. Thermostable L-arabinose isomerase and process for preparing D-tagatose. US Patent 6,933,138 issued 23 Aug. 2005; assigned to CJ Corp.

    Google Scholar 

  • Quah, H.M., Ooi, B.S., Seow-Choen, F., Sng, K.K., Ho, K.S. 2006. Prospective randomized crossover trial comparing fibre with lactulose in the treatment of idiopathic chronic constipation. Tech. Coloproctol. 10, 111–114.

    Article  CAS  Google Scholar 

  • Queen Mary University of London 2008. www.chem.qmul.ac.uk/iupac/2carb/, accessed 15 April 2008.

  • Quemener, B., Thibault, J.C., Coussement, P. 1994. Determination of inulin and oligofructose in food-products, and integration in the AOAC method for measurement of total dietary fiber. Lebensm. Wiss. Technol. 27, 125–132.

    Article  CAS  Google Scholar 

  • Rabiu, B.A., Jay, A.J., Gibson, G.R., Rastall, R.A. 2001. Synthesis and fermentation properties of novel galacto-oligosaccharides by β-galactosidases from Bifidobacterium species. Appl. Environ. Microbiol. 67, 2526–2530.

    Article  CAS  Google Scholar 

  • Rao, A.V. 1999. Dose-response effects of inulin and oligofructose on intestinal bifidogenesis effects. J. Nutr. 129 Suppl 7, 1442–1445.

    Google Scholar 

  • Rastall, R.A. 2006. Galacto-oligosaccharides as prebiotics. In: Prebiotics: Development and Application (G.R. Gibson, R.A. Rastall, eds.), pp. 101– 110, John Wiley & Sons, Ltd, Chichester, England.

    Google Scholar 

  • Rastall, R.A., Bucke, C. 1992. Enzymatic synthesis of oligosaccharides. Biotechnol. Gen. Eng. Rev. 10, 253–281.

    CAS  Google Scholar 

  • Reddy, G.P., Bush, C.A. 1991. High-performance anion exchange-chromatography of neutral milk oligosaccharides and oligosaccharide alditols derived from mucin glycoproteins. Anal. Biochem. 198, 278–284.

    Article  CAS  Google Scholar 

  • Rinne, M.M., Gueimonde, M., Kalliomäki, M., Hoppu, U., Salminen, S.J., Isolauri, E. 2005. Similar bifidogenic effects of prebiotic-supplemented partially hydrolyzed infant formula and breastfeeding on infant gut microbiota. FEMS Immunol. Med. Microbiol. 43, 59–65.

    Article  CAS  Google Scholar 

  • Roberfroid, M. 2007. Prebiotics: the concept revisited. J. Nutr. 137 Suppl. 2, 830S–837S.

    CAS  Google Scholar 

  • Roberts, H.R., Pettinati, J.D. 1957. Oligosaccharide production, concentration effects in the enzymatic conversion of lactose to oligosaccharides. J. Agric. Food Chem. 5, 130–134.

    Article  CAS  Google Scholar 

  • Rodriguez, A.P., Leiro, R.F., Trillo, C., Cerdan, E., Siso, I.G., Becerra, M. 2006. Secretion and properties of a hybrid Kluyveromyces lactis – Aspergillus niger β-galactosidase. Microbial Cell Factories 5, 41 (accessed at www.microbialcellfactories.com/content/5/1/41.).

  • Rowland, I.R., Bearne, C.A., Fischer, R., Pool-Zobel, B.L. 1996. The effect of lactulose on DNA damage induced by DMH in the colon of human flora-associated rats. Nutr. Cancer 26, 37–47.

    Article  CAS  Google Scholar 

  • Rowland, I.R., Tanaka. R. 1993. The effects of transgalactosylated oligosaccharides on gut flora metabolism in rats associated with a human faecal microflora. J. Appl. Bacteriol. 74, 667–674.

    Article  CAS  Google Scholar 

  • Ruffing, A., Chen, R.R. 2006. Metabolic engineering of microbes for oligosaccharide and polysaccharide synthesis. Microbial Cell Factories 5, 25 (accessed at www.microbialcellfactories.com/content/5/1/25).

  • Rumi, G., Tsubouchi, R., Okayama, M., Kato, S., Mózsik, G., Takeuchi, K. 2004. Protective effect of lactulose on dextran sulfate sodium-induced colonic inflammation in rats. Digest. Dis. Sci. 49, 1466–1472.

    Article  CAS  Google Scholar 

  • Saijonmaa, T., Heikonen, M., Kreula, M., Linko, P. 1978. Preparation and characterization of milk sugar alcohol, lactitol. Milchwissenschaft 33, 733–735.

    CAS  Google Scholar 

  • Saito, T., Kato, S., Maeda, T., Suzuki, S., Iijima, S., Kobayashi, T. 1992. Overproduction of thermostable β-galactosidase in Escherichia coli, its purification and molecular structure. J. Ferment. Bioeng. 74, 12–16.

    Article  CAS  Google Scholar 

  • Sakai, K., Katsumi, R., Ohi, H., Usui, T., Ishido, Y. 1992. Enzymatic syntheses of N-acetyllactosamine and N-acetylallolactosamine by the use of β-D-galactosidases. J. Carbohydr. Chem., 11, 553–565.

    Google Scholar 

  • Sako, T., Matsumoto, K., Tanaka, R. 1999. Recent progress on research and applications of non-digestible galacto-oligosaccharides. Int. Dairy J. 9, 69–80.

    Article  CAS  Google Scholar 

  • Santoso, B., Mwenya, B., Sar, C., Gamo, Y., Kobayashi, T., Morikawa, R., Kimura, K., Mizukoshi, H., Takahashi, J. 2004. Effects of supplementing galacto-oligosaccharides, Yucca schidigera or nisin on rumen methanogenesis, nitrogen and energy metabolism in sheep. Livestock Production Sci. 91, 209–217.

    Article  Google Scholar 

  • Sar, C., Santoso, B., Gamo, Y., Kobayashi, T., Shiozaki, S., Kimura, K., Mizukoshi, H., Arai, I., Takahashi, J. 2004. Effects of combination of nitrate with β1-4 galacto-oligosaccharides and yeast (Candida kefyr) on methane emission from sheep. Asian-Australasian J. Animal Sci. 17, 73–79.

    CAS  Google Scholar 

  • Satory, M., Furlinger, M., Haltrich, D., Kulbe, K.D., Pittner, F., Nidetzky, B. 1997. Continuous enzymatic production of lactobionic acid using glucose-fructose oxidoreductase in an ultrafiltration membrane reactor. Biotechnol. Lett. 19, 1205–1208.

    Article  CAS  Google Scholar 

  • Saunier, K., Doré, J. 2002. Gastrointestinal tract and the elderly: functional foods, gut microflora and healthy ageing. Dig. Liver Dis. 34, suppl S 19–S24.

    Article  Google Scholar 

  • Scholnick, F., Ben-Et, G., Sucharski, M.K. Maurer, E.W., Linfield, W.M. 1975. Lactose-derived surfactants: II. Fatty esters of lactitol. J. Am. Oil Chem. Soc. 52, 256–258.

    Article  CAS  Google Scholar 

  • Schoterman, H.C. 2001. Galactooligosaccharides: properties and health aspects. In: Advanced Dietary Fibre Technology (D.B.V. McCleary, L. Prosky, eds.), pp. 494– 502, Blackwell Publishing, UK.

    Google Scholar 

  • Schultz, M., Timmer, A., Herfarth, H.H., Sartor, R.B., Vanderhoof, J.A., Rath, H.C. 2004. Lactobacillus GG in inducing and maintaining remission of Crohn's disease. BMC Gastroenterol. 4, 5 (15 March 2004).

    Article  Google Scholar 

  • Schumann, C. 2002. Medical, nutritional and technological properties of lactulose. An update. Eur. J. Nutr. 41 Suppl 1, 17–25.

    Google Scholar 

  • Senderens, J.B. 1920. Hydrogenation catalytique du lactose Compt. Rend. 170, 47–50 [in French].

    CAS  Google Scholar 

  • She, Q., et al. 2001. The complete genome of the crenarchaeon Sulfolobus solfataricus P2. Proc. Natl. Acad. Sci. USA 98, 7835–7840.

    Article  CAS  Google Scholar 

  • Shimomura, Y., Maeda, K., Nagasaki, M., Matsuo, Y., Murakami, T., Bajotto, G., Sato, J., Seino, T., Kamiwaki, T., Suzuki, M. 2005. Attenuated response of the serum triglyceride concentration to ingestion of a chocolate containing polydextrose and lactitol in place of sugar. Biosci. Biotechnol. Biochem. 69, 1819–1823.

    Article  CAS  Google Scholar 

  • Shin, H.J., Park, J.M., Yang, J.W. 1995. Optimum culture condition of Bullera singularis for galactooligosaccharide production. Kor. J. Appl. Microbiol. Biotechnol. 23, 593–598.

    Google Scholar 

  • Shin, H.J., Park, J.M., Yang, J.W. 1998. Continuous production of galacto-oligosaccharides from lactose by Bullera singularis β-galactosidase immobilized in chitosan beads. Process Biochem. 33, 787–792.

    Article  CAS  Google Scholar 

  • Shoaf, K., Mulvey, G.L., Armstrong, G.D., Hutkins, R.W. 2006. Prebiotic galactooligosaccharides reduce adherence of enteropathogenic Escherichia coli to tissue culture cells. Infect. Immun. 74, 6920–6928.

    Article  CAS  Google Scholar 

  • Sienkiewicz, T., Riedel, C.-L. 1990. Whey and Whey Utilization, 2nd edn. Verlag Th. Mann, Gelsenkirchen-Buer, Germany.

    Google Scholar 

  • Sigma-Aldrich. 2007. Biofiles Vol. 2, No. 1, pp. 4–5.

    Google Scholar 

  • Smart, J.B. 1989. Physiologically interesting side reactions of β-galactosidase. Proc. 8th Australian Biotechnol. Conf., Sydney, pp. 337–340.

    Google Scholar 

  • Smart, J.B. 1991. Transferase reactions of the β-galactosidase from Streptococcus thermophilus. Appl. Microbiol. Technol. 34, 495–501.

    Article  CAS  Google Scholar 

  • Smart, J.B. 1993. Transferase Reactions of β-galactosidases – New Product Opportunities. Bulletin 289, International Dairy Federation, Brussels, pp. 16–22.

    Google Scholar 

  • Southgate, D.A.T., Hudson, G.J., Englyst, H. 1978. The analysis of dietary fibre- the choices for the analyst. J. Sci. Food Agric. 29, 979–988.

    Article  CAS  Google Scholar 

  • Swanson, K.S., Fahey Jr, G.C. 2006. Prebiotic impacts on companion animals. In: Prebiotics: Development and Application (G.R. Gibson, R.A. Rastall, eds.), pp. 213– 236, John Wiley & Sons, Ltd, Chichester, England.

    Google Scholar 

  • Takaichi, A., Okamoto, T., Azuma, Y., Watanabe, Y., Matsumoto, T., Miyata, K.,Sakamoto, S., Okamatsu, H. et al. 1995. Food composition for inhibiting the formation of an intestinal putrefactive product. US Patent 5,455,235., Oct 3, 1995, assigned to Otsuka Pharmaceutical Co., Ltd.

    Google Scholar 

  • Tamura, Y., Mizota, T., Shimamura, S., Tomita, M. 1993. Lactulose and its Application to the Food and Pharmaceutical Industries. Bulletin 289, International Dairy Federation, Brussels. pp. 43–53.

    Google Scholar 

  • Tamura, Z. 1983. Nutriology of bifidobacteria. Bifidobacteria Microflora 2, 3–16.

    CAS  Google Scholar 

  • Tanaka, R., Matsumoto, K. 1998. Recent Progress on Prebiotics in Japan, Including Galacto-oligosaccharides. Bulletin 336, International Dairy Federation, Brussels, pp. 21–27.

    Google Scholar 

  • Tannock, G.W., Munro, K., Bibiloni, R., Simon, M.A., Hargreaves, P., Gopal, P., Harmsen, H., Welling, G. 2004. Impact of consumption of oligosaccharide-containing biscuits on the fecal microbiota of humans. Appl. Environ. Microbiol. 70, 2129–2136.

    Article  CAS  Google Scholar 

  • Terada, A., Hara, H., Katoaka, M., Mitsuoka, T. 1992. Effect of lactulose on the composition and metabolic activity of human faecal flora. Microbial Ecol. Health Dis. 5, 43–50.

    Article  Google Scholar 

  • Thebaudin, J.Y., Lefebvre, A.C., Harrington, M., Bourgeois, C.M. 1997. Dietary fibres: nutritional and technological interest. Trends Food Sci. Technol. 8, 41–48.

    Article  CAS  Google Scholar 

  • Thelwall, L.A.W. 1997. Lactose: chemical derivatives. In: Advanced Dairy Chemistry (P.F. Fox, ed.), pp. 39– 76, Vol. 3, 2nd Edition, P.F. Fox, ed., Chapman & Hall, London.

    Google Scholar 

  • Tlaskalova-Hogenova, H., Stepankova, R., Hudcovic, T., Tuckova, L.,Cukrowska, B., Lodinova-Zadnkova, R., Kozakova, H., Rossmann, P., Bartova, J., Sokol, D., Funda, D.P., Borovska, D., Rehakova, Z., Sinkora, J., Hofman, J., Drastich, P., Kokesova, A. 2004. Commensal bacteria (normal microflora), mucosal immunity and chronic inflammatory and autoimmune diseases. Immunol. Lett. 93, 97–108.

    Article  CAS  Google Scholar 

  • Toba, T., Adachi, S. 1978. Hydrolysis of lactose by microbial β-galactosidases. Formation of oligosaccharide with special reference to 2-O-β-D-galactopyranosyl-D-glucose. J. Dairy Sci. 61, 33–38.

    Article  CAS  Google Scholar 

  • Toba, T., Tomita, Y., Itoh, T., Adachi, S. 1981. β-Galactosidases of lactic acid bacteria: characterization by oligosaccharides formed during hydrolysis of lactose. J. Dairy Sci. 64, 185–192.

    Article  CAS  Google Scholar 

  • Toba, T., Yokota, A., Adachi, S. 1985. Oligosaccharide structures formed during the hydrolysis of lactose by Aspergillus oryzae β-galactosidase. Food Chem. 16, 147–162.

    Article  CAS  Google Scholar 

  • Tomito, M., Shimamura, S., Tamura, Y., Mizota, T., Nakano, S., Suzawa, I. 1994. Crystalline lactulose trihydrate and a method for its manufacture. US Patent 5304251, publication date Apr. 19, 1994, assigned to Morinaga Milk Industry Co., Ltd.

    Google Scholar 

  • Topping, D.L., Clifton, P.M. 2001. Short-chain fatty acids and human colonic function: roles of resistant starch and nonstarch polysaccharides. Physiol. Rev. 81, 1031–1064.

    CAS  Google Scholar 

  • Townsend, R.R., Hardy, M.R., Hindsgaul, O., Lee, Y.C. 1988. High-performance anion-exchange chromatography of oligosaccharides using pellicular resins and pulsed amperometric detection. Anal. Biochem. 174, 459–470.

    Article  CAS  Google Scholar 

  • Tuohy, K.M., Ziemer, C.J., Klinder, A., Knobel, Y., Pool-Zobel, B.L., Gibson, G.R. 2002. A human volunteer study to determine the prebiotic effects of lactulose powder on human colonic microbiota. Microbial Ecol. Health Dis. 14, 165–173.

    Article  Google Scholar 

  • Tzortzis, G., Goulas, A.K., Gibson, G.R. 2005a. Synthesis of prebiotic galactooligosaccharides using whole cells of a novel strain, Bifidobacterium bifidum NCIMB 41171. Appl. Microbiol. Biotechnol. 68, 412–416.

    Article  CAS  Google Scholar 

  • Tzortzis, G., Goulas, A.K., Gee, J.M., Gibson, G.R. 2005b. A novel galactooligosaccharide mixture increases the bifidobacterial population numbers in a continuous in vitro fermentation system and in the proximal colonic contents of pigs in vivo. J. Nutr. 135, 1726–1731.

    CAS  Google Scholar 

  • Usui T., Kubota, S., Ohi, H. 1993. A convenient synthesis of β-galactosyl disaccharide derivatives using the β-D-galactosidase from Bacillus circulans. Carbohydr. Res. 244, 315–323.

    Article  CAS  Google Scholar 

  • Van den Heuvel, E.G., Muijs, T., van Dokkum, W., Schaafsma, G. 1999. Lactulose stimulates calcium absorption in post-menopausal women. J. Bone Mineral Res. 14, 1211–1216.

    Article  Google Scholar 

  • Van den Heuvel, E.G., Schoterman, M.H.C., Muijs, T. 2000. Transgalactooligosaccharides stimulate calcium absorption in post-menopausal women. J. Nutr. 130, 2938–2942.

    Google Scholar 

  • Vanhoutte, T., De Preter, V., De Brandt, E., Verbeke, K., Swings, J., Huys, G. 2006. Molecular monitoring of the fecal microbiota of healthy human subjects during administration of lactulose and Saccharomyces boulardii. Appl. Environ. Microbiol. 72, 5990–5997.

    Article  CAS  Google Scholar 

  • Van Laere, K.M.J., Abee, T., Schols, H.A., Beldman, G., Voragen, A.G.J. 2000. Characterization of a novel β-galactosidase from Bifidobacterium adolescentis DSM 20083 active towards transgalactooligosaccharides. Appl. Environ. Microbiol. 66, 1379–1384.

    Article  Google Scholar 

  • Van Loveren, C. 2004. Sugar alcohols: what is the evidence for caries-preventive and caries-therapeutic effects? Caries Res. 38, 286–293.

    Article  CAS  Google Scholar 

  • Van Riel, J., Olieman, C. 1991. Selectivity control in the anion-exchange chromatographic determination of saccharides in dairy products using pulsed amperometric detection. Carbohyd. Res. 215, 39–46.

    Article  Google Scholar 

  • Van Soest, P.J. 1978. Dietary fibers: their definition and nutritional properties. Am. J. Clin. Nutr. 31 Suppl., S12–S20.

    Google Scholar 

  • Van Velthuijsen, J.A. 1979. Food additives derived from lactose: lactitol and lactitol palmitate. J. Agric. Food Chem. 27, 680–686.

    Article  Google Scholar 

  • Vogt, J.A., Ishii-Schrade, K.B., Pencharz, P.B., Jones, P.J.H., Wolever, T.M.S. 2006. L-Rhamnose and lactulose decrease serum triacylglycerols and their rates of synthesis, but do not affect serum cholesterol concentrations in men. J. Nutr. 136, 2160–2166.

    CAS  Google Scholar 

  • Wallenfels, K. 1951. Enzymatische synthese von oligosacchariden aus disacchariden. Naturwissenschaften 38, 306–307.

    Article  CAS  Google Scholar 

  • Williams, C.M., Jackson, K.G. 2002. Inulin and oligofructose: effects on lipid metabolism from human studies. Br. J. Nutr. 87, Suppl 2, S261–S264.

    Article  CAS  Google Scholar 

  • Yanahira, S., Suguri, T., Yakabe, T., Ikeuchi, Y., Hanagata, G., Deya, E. 1992. Formation of oligosaccharides from lactitol by Aspergillus oryzae β-D-galactosidase. Carbohyd. Res. 232, 151–159.

    Article  CAS  Google Scholar 

  • Yanahira, S., Kobayashi, T., Suguri, T., Nakakoshi, M., Miura, S., Ishikawa, H., Nakajima, I. 1995. Formation of oligosaccharides from lactose by Bacillus circulans β-galactosidase. Biosci. Biotechnol. Biochem. 59, 1021–1026.

    Article  CAS  Google Scholar 

  • Yazawa, K., Tamura, Z. 1982. Search for sugar sources for selective increase of bifidobacteria. Bifidobacteria Microflora, 1, 34–44.

    Google Scholar 

  • Yazawa, K., Imai, K., Tamura, Z. 1978. Oligosaccharides and polysaccharides specifically utilizable by bifidobacteria. Chem. Pharm. Bull. (Tokyo) 26, 3306–3311.

    Article  CAS  Google Scholar 

  • Yoneyama, M., Mandai, T., Aga, H., Fujii, K., Sakai, S., Katayama, Y. 1992. Effects of 4-β-d-galactosylsucrose (lactosucrose) intake on intestinal flora in healthy humans. J. Jap. Soc. Nutr. Food Sci. 45, 101–107.

    Article  CAS  Google Scholar 

  • Ziegler, E., Vanderhoof, J.A., Petschow, B., Mitmesser, S.H., Stolz, S.I., Harris, C.L., Berseth, C.L. 2007. Term infants fed formula supplemented with selected blends of prebiotics grow normally and have soft stools similar to those reported for breast-fed infants. J. Pediatr. Gastroenterol. Nutr. 44, 359–364.

    Article  CAS  Google Scholar 

  • Zopf, D., Roth, S. 1996. Oligosaccharide anti-infective agents. Lancet 347, 1017–1021.

    Article  CAS  Google Scholar 

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Acknowledgments

Ms Janet Werkmeister and staff of the Information Resource Centre, Dairy Australia, Melbourne and Ms Bee Thia of the CSIRO Ian Wark Laboratory are thanked for their bibliographic assistance.

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  1. Melbourne Biotechnology, 1 Lorraine Street, Hampton, Victoria, 3188, Australia

    M.J. Playne

  2. Food Science Australia, Private Bag 16, Werribee, Victoria, 3188, Australia

    R.G. Crittenden

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  1. Fac. Food Technology & Nutrition, Dept. Food Science, University College Cork, Cork, Ireland

    Paul McSweeney

  2. Fac. Food Technology & Nutrition, Dept. Food Science, University College Cork, Cork, Ireland

    Patrick F. Fox

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Playne, M., Crittenden, R. (2009). Galacto-oligosaccharides and Other Products Derived from Lactose. In: McSweeney, P., Fox, P. (eds) Advanced Dairy Chemistry. Springer, New York, NY. https://doi.org/10.1007/978-0-387-84865-5_5

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