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Abstract

The properties and reactions of the oligosaccharides are best understood by considering them as substituted monosaccharides. It has been noted that the potential carbonyl group of a monosaccharide can react with alcohol functions to form anhydro sugars (glycosans), true acetals, or glycosides, depending on whether the acetal formation is intramolecular, intermolecular, or both (p. 21). The normal glycosides, with an alkyl or aryl aglycon, may be designated as heterosides. When the glycosidic radical is also a monosaccharide, the product would be a disaccharide or holoside.

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Literature

  • Albon, N., D.J. Bell, P. H. Blanchard, D. Gross and J. T. Rundell: Kestose: A trisaccharide formed from sucrose by yeast invertase. J. Chem. Soc. (Lond.) 1953, 24–27.

    Google Scholar 

  • Andrews, P., and J. K. N. Jones: [1] The isolation of oligosaccharides from gums and mucilages. Part II. J. Chem. Soc. (Lond.) 1954, 1724–1726.

    Google Scholar 

  • [2] The isolation of oligosaccharides from gums and mucilages. Part III. Golden apple gum. J. Chem. Soc. (Lond.) 1954, 4134–4138.

    Google Scholar 

  • [3] The isolation of oligosaccharides from gums and mucilages. Part IV. The isolation of 3-O-β-l-arabopyranosyl-l-arabinose from lemon gum. J. Chem. Soc. (Lond.) 1955, 583–584.

    Google Scholar 

  • Bächli, P., and E. G. V. Percival: The synthesis of laminaribiose (3-β-d-glucosyl d-glucose) and proof of its identity with laminaribiose isolated from laminarin. J. Chem. Soc. (Lond.) 1952, 1243–1246.

    Google Scholar 

  • Barker, S. A., E. J. Bourne and T. R. Carrington: [1] Studies of Aspergillus niger. Part III. The structure of a trisaccharide synthesized from sucrose. J. Chem. Soc. (Lond.) 1954, 2125–2129.

    Google Scholar 

  • Barker, S. A., E. J. Bourne and M. Stagey: [2] Studies of Aspergillus niger. Part I. The structure of the polyglucosan synthesized by Aspergillus niger. J. Chem. Soc. (Lond.) 1953, 3084–3090.

    Google Scholar 

  • Barker, S. A., E. J. Bourne, M. Stagey and D. H. Whiffen: [3] Infrα-red spectra of carbohydrates. Part I. Some derivatives of d-glucopyranose. J. Chem. Soc. (Lond.) 1954, 171–176.

    Google Scholar 

  • Barry, V. C.: Hydrolysis of laminarin. Isolation of a new glucose dissaccharide. Sci. Proc. Roy. Dublin Soc. 22, 423–429 (1941).

    CAS  Google Scholar 

  • Bates, F. J., and Associates: Polarimetry, saccharimetry and the sugars. Washington: United States Government Printing Office. 1942.

    Google Scholar 

  • Charlson, A. J., J. R. Nunn and A. M. Stephen: [1] The composition of Acacia cyanophylla gum. J. Chem. Soc. (Lond.) 1955, 269–273.

    Google Scholar 

  • [2] Acacia karroo gum. J. Chem. Soc. (Lond.) 1955, 1428–1431.

    Google Scholar 

  • Evans, W. L., D.D. Reynolds and E. A. Talley: The synthesis of oligosaccharides. Adv. Carbohydrate Chem. 6, 27–81 (1951).

    Article  CAS  Google Scholar 

  • French, D.: [1] The raffinose family of oligosaccharides. Adv. Carbohydrate Chem. 9, 149–184 (1954).

    Article  CAS  Google Scholar 

  • [2] Isolation and identification of planteose from tobacco seeds. J. Amer. Chem. Soc. 77, 1024–1025 (1955).

    Google Scholar 

  • Gilbert, V. E., F. Smith and M. Stacey: A constitutional synthesis of cellobiose and gentiobiose. J. Chem. Soc. (Lond.) 1946, 622–625.

    Google Scholar 

  • Gill, R. E., E. L. Hirst and J. K. N. Jones: Constitution of the mucilage from the bark of Ulmus fulva (slippery elm mucilage). Part I. The aldobionic acid obtained by hydrolysis of the mucilage. J. Chem. Soc. (Lond.) 1939, 1469–1471.

    Google Scholar 

  • Gross, D., P. H. Blanchard and D. J. Bell: A trisaccharide formed from sucrose by yeast invertase. J. Chem. Soc. (Lond.) 1954, 1727–1730.

    Google Scholar 

  • Harding, T. S.: The source of rare sugars IX. History of trehalose, its discovery and methods of preparation. Sugar 25, 476–477 (1923).

    CAS  Google Scholar 

  • Haskins, W. T., R. M. Hann and C. S. Hudson: Syntheses of epi-lactose and lactose. J. Amer. Chem. Soc. 64, 1852–1856 (1942).

    Article  CAS  Google Scholar 

  • Hassid, W. Z., and M. Doudoroff: Enzymatic synthesis of sucrose and other disaccharides. Adv. Carbohydrate Chem. 5, 29–48 (1950).

    Article  CAS  Google Scholar 

  • Haworth, W. N.: [1] Organic chemistry. Part I. Aliphatic division. Ann. Rep. Progr. Chem. 24, 61–105 (1927).

    Article  Google Scholar 

  • Haworth, W. N., and W. J. Hickinbottom: [2] Synthesis of anew disaccharide, neotrehalose. J. Chem. Soc. (Lond.) 1931, 2847–2850.

    Google Scholar 

  • Hehre, E. J.: The substituted-sucrose structure of melezitose. Adv. Carbohydrate Chem. 8, 277–290 (1953).

    Article  CAS  Google Scholar 

  • Heidelberger, M., and W. F. Goebel: The soluble specific substance of Pneumococcus. V. On the chemical nature of the aldobionic acid from the specific polysaccharide of type III Pneumococcus. J. of Biol. Chem. 74, 613–618 (1927).

    CAS  Google Scholar 

  • Helferich, B., u. H. Bredereck: [1] Zuckersynthesen. VIII. Liebigs Ann. 465, 166–184 (1928).

    Article  CAS  Google Scholar 

  • Helferich, B., u. W. Klein: [2] Zur Synthese von Disacchariden. IV. Zweei Tetra-acetyl-β-d-glucosen. Liebigs Ann. 450, 219–229 (1926).

    Article  CAS  Google Scholar 

  • Hill, A. C.: Reversible zymohydrolysis. J. Chem. Soc. (Lond.) 1898, 634–658.

    Google Scholar 

  • Hirst, E. L., and A. S. Berlin: The gum of Acacia pycnantha. J. Chem. Soc. (Lond.) 1954, 2622–2627.

    Google Scholar 

  • Hotchkiss, R. D., and W. F. Goebel: Chemo-immunological studies on the soluble specific substance of Pneumococcus. III. The structure of the aldobionic acid from the type III polysaccharide. J. of Biol. Chem. 121, 195–203 (1937).

    CAS  Google Scholar 

  • Hough, L., J. K. N. Jones and W. H. Wadman: Quantitative analysis of mixtures of sugars by the method of partition chromatography. Part IV. The separation of sugars and their methylated derivatives on columns of powdered cellulose. J. Chem. Soc. (Lond.) 1949, 2511–2516.

    Google Scholar 

  • Hudson, C. S.: [1] The inversion of cane sugar by invertase. J. Amer. Chem. Soc. 30, 1160–1166, 1564–1583 (1908); 31, 655–664 (1909).

    Article  CAS  Google Scholar 

  • [2] Some numerical relations among the rotatory powers of the compound sugars. J. Amer. Chem. Soc. 38, 1566–1575 (1916).

    Google Scholar 

  • [3] The structure of turanose. J. Org. Chem. 9, 470–476 (1944).

    Google Scholar 

  • [4] Melezitose and turanose. Adv. Carbohydrate Chem. 2, 1–36 (1946).

    Google Scholar 

  • Jackson, E. L., and C. S. Hudson: The periodic acid oxidation of α,α-trehalose. J. Amer. Chem. Soc. 61, 1530–1532 (1939).

    Article  CAS  Google Scholar 

  • Jackson, J., and F. Smith: The constitution of arabic acid. Part IV. The formation of 3-galactosidogalactose by hydrolysis of degraded arabic acid. J. Chem. Soc. (Lond.) 1940, 79–82.

    Google Scholar 

  • Jones, J. K. N., and W. W. Reid: The structure of the oligosaccharides produced by the enzymic breakdown of pectic acid. J. Chem. Soc. (Lond.) 1954, 1361–1365.

    Google Scholar 

  • Lemieux, R. U., and G. Huber: A chemical synthesis of sucrose. J. Amer. Chem. Soc. 75, 4118 (1953).

    Article  CAS  Google Scholar 

  • Levi, L, and C. B. Purves: The structure and configuration of sucrose. Adv. Carbohydrate Chem. 4, 1–35 (1949).

    Article  CAS  Google Scholar 

  • Linstead, R. P., A. Rutenberg, W. G. Dauben and W. L. Evans: The stable form of sucrose octaacetate. J. Amer. Chem. Soc. 62, 3260–3263 (1940).

    Article  CAS  Google Scholar 

  • Mc Closkey, C. M., and G. H. Coleman: The preparation of β-primverose heptaacetate and β-vicianose heptaacetate. J. Amer. Chem. Soc. 65, 1778–1780 (1943).

    Article  CAS  Google Scholar 

  • Mc Neely, W. H., W. W. Binkley and M. L. Wolfrom: Separation of sugar acetates by chromatography. J. Amer. Chem. Soc. 67, 527–529 (1945).

    Article  CAS  Google Scholar 

  • Pan, S. C., L. W. Nicholson and P. Kolachov: [1] Isolation of a crystalline trisaccharide from the unfermentable carbohydrate produced enzymically from maltose. J. Amer. Chem. Soc. 73, 2547–2550 (1951).

    Article  CAS  Google Scholar 

  • [2] Enzymic synthesis of oligosaccharides—a transglycosidation. Arch. of Biochem. a. Biophysics 42, 406–420 (1953).

    Google Scholar 

  • Pazur, J. H., and A. L. Gordon Studies on inulin. The preparation and properties of inulobiose. J. Amer. Chem. Soc.: 3458–3460 (1953).

    Google Scholar 

  • Peat, S., W. J. Whelan and K. A. Hinson: [1] Synthetic action of almond emulsin. Nature (Lond.) 170, 1056–1057 (1952).

    Article  CAS  Google Scholar 

  • [2] The enzymic polymerization of glucose. Chem. a. Ind. 1955, 385.

    Google Scholar 

  • Purves, C. B., and C. S. Hudson: The analysis of γ-fructoside mixtures by means of invertase. V. Methylated and acetylated derivatives of crystalline α-methyl- and α-benzyl-fructofuranoside. J. Amer. Chem. Soc. 59, 49–56 (1937).

    Article  CAS  Google Scholar 

  • Rabaté, J.: Etude du sophorose. Bull. Soc. chim. France 1940, 565–569.

    Google Scholar 

  • Richter, D.: Anthraquinone colouring matters: ruberythric acid. J. Chem. Soc. (Lond.) 1936, 1701–1703.

    Google Scholar 

  • Richter, F.: Kohlenhydrate. Teil I: Monosaccharide und Oligosaccharide. Beilsteins Handbuch der Organischen Chemie. Berlin: Springer 1938.

    Google Scholar 

  • Schlubach, H. H., u. K. Maurer: Synthesen von Polysacchariden, L: Synthese einer Iso-trehalose. Ber. dtsch. chem. Ges. 58, 1178–1184 (1925).

    Article  Google Scholar 

  • Smith, F.: The constitution of arabic acid. Part I. The isolation of 3-d-galactosido-l-arabinose. J. Chem. Soc. (Lond.) 1939, 744–753.

    Google Scholar 

  • Thompson, A., K. Anno, M. L. Wolfrom and M. Inatome: [1] Acid reversion products from d-glucose. J. Amer. Chem. Soc. 76, 1309–1311 (1954).

    Article  CAS  Google Scholar 

  • Thompson, A., and M. L. Wolfrom: [2] Degradation of amylopectin to panose. J. Amer. Chem. Soc. 73, 5849–5850 (1951).

    Article  CAS  Google Scholar 

  • [3] The structure of maltotriose. J. Amer. Chem. Soc. 74, 3612–3614 (1952).

    Google Scholar 

  • Thompson, A., M. L. Wolfrom and E. J. Quinn: [4] Acid reversion in relation to isomaltose as a starch hydrolytic product. J. Amer. Chem. Soc. 75, 3003–3004 (1953).

    Article  CAS  Google Scholar 

  • Tollens, B., u. H. Elsner: Kurzes Handbuch der Kohlenhydrate. Leipzig: Johann Ambrosius Barth 1953.

    Google Scholar 

  • Wehmer, C.: Die Pflanzenstoffe, 2. Aufl. Jena: Gustav Fischer 1929–1935.

    Google Scholar 

  • Weissmann, B., and K. Meyer: The structure of hyalobiuronic acid and of hyaluronic acid from umbilical cord. J. Amer. Chem. Soc. 76, 1753–1757 (1954).

    Article  CAS  Google Scholar 

  • Whistler, R. L., and H. E. Conrad: [1] A crystalline galactobiose from acid hydrolysis of okra mucilage. J. Amer. Chem. Soc. 76, 1673–1674 (1954).

    Article  CAS  Google Scholar 

  • [2] 2-O-(d-Gaiactopyranosyluronic acid)-l-rhamnose from okra mucilage. J. Amer. Chem. Soc. 76, 3544–3546 (1954).

    Google Scholar 

  • Whistler, R. L., H. E. Conrad and L. Hough: [3] 2-O-(4-O-Methyl-α-d-glucopyranosyluronic acid)-d-xylose from hemicellulose-B of corn cob. J. Amer. Chem. Soc. 76, 1668–1670 (1954).

    Article  CAS  Google Scholar 

  • Whistler, R. L., and J. H. Duffy: [4] Maltopentaose and crystalline octadeca-O-acetylmaltopentaitol J. Amer. Chem. Soc. 77, 1017–1019 (1955).

    Article  CAS  Google Scholar 

  • Whistler, R. L., and D. F. Durso: [5] Chromatographic separation of sugars on charcoal. J. Amer. Chem. Soc. 72, 677–679 (1950).

    Article  CAS  Google Scholar 

  • [6] A new crystalline trisaccharide from partial acid hydrolysis of guaran and the structure of guaran. J. Amer. Chem. Soc. 74, 5140–5141 (1952).

    Google Scholar 

  • Whistler, R. L., and J. L. Hickson: [7] Maltotetraose and crystalline pentadecaacetylmaltotetraitol. J. Amer. Chem. Soc. 76, 1671–1673 (1954).

    Article  CAS  Google Scholar 

  • Whistler, R. L., and L. Hough: [8] Two further aldobiuronic acids from hemicellulose-B of corn cob. J. Amer. Chem. Soc. 75, 4918–4919 (1953).

    Article  CAS  Google Scholar 

  • Whistler, R. L., and D. I. Mc Gilvray: [9] Chemistry of the carbohydrates. Annual Rev. Biochem. 23, 79–98 (1954).

    Article  CAS  Google Scholar 

  • [10] 2-O-α-d-Xylopyranosyl-l-arabinose from hemicellulose-B of corn cob. J. Amer. Chem. Soc. 77, 1884–1885 (1955).

    Google Scholar 

  • [11] An aldotriuronic acid from hemicellulose-B of corn cob. J. Amer. Chem. Soc. 77, 2212–2213 (1955).

    Google Scholar 

  • Whistler, R. L., and C. G. Smith: [12] A crystalline mannotriose from the enzymic hydrolvsis of guaran. J. Amer. Chem. Soc. 74, 3795–3796 (1952).

    Article  CAS  Google Scholar 

  • Whistler, R. L., and C.-C. Tu: [13] Crystalline xylobiose and xylotriose. J. Amer. Chem. Soc. 73, 1389–1390 (1951).

    Article  CAS  Google Scholar 

  • [14] Isolation and properties of a series of crystalline oligosaccharides from xylan. J. Amer. Chem. Soc. 74, 3609–3612 (1952).

    Google Scholar 

  • [15] Crystalline xyloheptaose. J. Amer. Chem. Soc. 75, 645–647 (1953).

    Google Scholar 

  • White jr., J. W., and J. Maher: α-Maltosyl β-d-fructofuranoside, a trisaccharide enzymically synthesized from sucrose. J. Amer. Chem. Soc. 75, 1259–1260 (1953).

    Article  CAS  Google Scholar 

  • Wolfrom, M. L.: [1] Carbohydrates. I. Organic chemistry, H. Gilman, ed., 1st Edit., vol. 2, pp. 1399–1476. New York: John Wiley & Sons 1938.

    Google Scholar 

  • Wolfrom, M. L., and J. C. Dacons: [2] The polymer-homologous series of oligosaccharides from cellulose. J. Amer. Chem. Soc. 74, 5331–5333 (1952).

    Article  CAS  Google Scholar 

  • Wolfrom, M. L., L. W. Georges and I. L. Miller: [3] Crystalline derivatives of isomaltose. J. Amer. Chem. Soc. 71, 125–127 (1949).

    Article  CAS  Google Scholar 

  • Wolfrom, M. L., and F. Shafizadeh: [4] An evaluation of Hudson’s classical studies on the configuration of sucrose. J. Org. Chem. 21, 88–89 (1956).

    Article  CAS  Google Scholar 

  • Wolfrom, M. L., and A. Thompson: [5] Degradation of amvlopectin to nigerose. J. Amer. Chem. Soc. 77, 6403 (1955).

    Article  CAS  Google Scholar 

  • Zemplén, G., u. A. Gerecs: Konstitution und Svnthese der Rutinose, der Biose des Rutins. Ber. dtsch. chem. Ges. 68, 1318–1321 (1935).

    Article  Google Scholar 

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Shafizadeh, F., Wolfrom, M.L. (1958). Structure, properties and occurrence of the oligosaccharides. In: Åberg, B., et al. Aufbau · Speicherung · Mobilisierung und Umbildung der Kohlenhydrate / Formation · Storage · Mobilization and Transformation of Carbohydrates. Handbuch der Pflanzenphysiologie / Encyclopedia of Plant Physiology, vol 6. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-94731-5_4

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