Summary
Free L- and D-amino acids (L-AA, D-AA) were isolated from an Appenzeller cheese, from raw milk, and from an ethanolic extract as well as a total hydrolysate of cow's rumen microorganisms, and their relative amounts were determined by reversed-phase high-performance liquid chromatography after derivatization witho-phthaldialdehyde together withN-isobutyryl-L-(or D)-cysteine. D-Ala, D-Asp and D-Glu were found, among other D-AA in all cases and a microbial origin of free D-AA found in cheese and milk was rationalized. From the results, and taking other findings of the occurrence of D-AA in food and beverages into account, the highest intake of D-AA is to be expected from the consumption of ripened cheeses. From the presence of D-amino acid oxidases in human kidney, liver, and brain and from reports on the intravenous administration of racemic AA to humans and their metabolisation it is concluded that intake of free D-AA found in food is no threat for human beings.
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References
Adams E (1972) Racemases and epimerases. In: Boyer PD (ed) The enzymes, vol 6. Academic Press, New York, pp 479–507
Armani E, Barazzoni L, Dossena A, Marchelli R (1988) J Chromatogr 441: 287–298
Bansi HW, Jürgens P, Müller G, Rostin M (1964) Klin Wochenschr 42: 332–352
Barker RF, Hopkinson DA (1977) Ann Hum Genet Lond 41: 27–42
Bhattacharyya SR, Banerjee AB (1974) Folia Microbiol 19: 43–50
Bottazzi V (1988) Biochimie 70: 303–315
Brückner H, Hausch M (1989) J High Resol Chromatogr 12: 680–684
Brückner H, Hausch M (1989a) Chromatographia 28: 487–492
Brückner H, Hausch M (1990) Milchwissenschaft 45: 357–360
Brückner H, Hausch M (1990a) Milchwissenschaft 45: 421–425
Brückner H, Hausch M (1990b) D-Amino acids as ubiquitous constitutents in fermented food. In: Lubec G, Rosenthal GA (eds) Amino acids: chemistry, biology and medicine. Escom Science, Leiden, pp 1172–1182
Brückner H, Lüpke M (1991) Chromatographia 31: 123–128
Brückner H, Wittner R, Godel H (1991) Chromatographia 32: 383–388
Cherken A, Davis JL, Garman MW (1978) Parmacol Biochem Behav 8: 623–625
Corrigan JJ (1969) Science 164: 142–149
Cousins CM, Bramley AJ (1981) The microbiology of raw milk. In: Robinson RK (ed) Dairy microbiology, vol 1. Applied Science Publishers, London, pp 119–163
D'Aniello A, Giuditta A (1979) Comp Biochem Physiol 66B: 319–322
Einarsson S, Josefsson B, Möller P, Sanchez D (1987) Anal Chem 59: 1191–1195
Felbeck H, Wiley S (1987) Biol Bull 173: 252–259
Friedman M, Gumbmann R (1989) Dietary significance of D-amino acids. In: Friedman M (ed) Absorption and utilization of amino acids, vol 2. CRC Press, Boca Raton, FA, pp 173–190
Ganote CE, Peterson DR, Carone FA (1974) Am J Pathol 77: 269–276
Gübitz G, Juffmann F, Jellenz W (1982) Chromatographia 16: 103–106
Hare PE, Gil-Av E (1979) Science 204: 1226–1228
Heine W, Drescher U (1975) Dtsch Gesundheitswesen 30: 1563–1566
Heine W, Wutzke K, Drescher U (1983) Clin Nutr 2: 31–35
Hofsommer HJ, Klein I, Grüning J, Höpker HR (1989) Flüssig Obst 56: 646–651
Holmes CW, Wilson GF (1987) Milk production from pasture. Butterworths, Wellington, New Zealand, pp 88–106
Hungate R (1966) The Rumen and its microbes. Academic Press, New York
Kampel D, Kupferschmidt R, Lubec G (1991) Toxicity of D-proline. In: Lubec G, Rosenthal GA (eds) Amino acids: chemistry, biology and medicine. Escom Science, Leiden, pp 1164–1171
Konno R, Yasumura Y (1981) Zoological Magazine Jpn 90: 368–373
Krebs HA (1948) Biochem Soc Symp Camb 1: 2–19
Langer M, Wittner R, Jaek P, Godel H, Brückner H (1991) Determination of amino acid enantiomers in food and beverages by HPLC and GC. In: Baltes WJ, Eklund T, Fenwick R, Pfannhauser W, Ruiter A, Thier HP (eds) Strategies for food quality control and analytical methods in Europe. Proceedings of Europ Food Chem VI, Hamburg, September 22–26, 1991. Behr's Verlag, Hamburg, pp 385–390
Liardon R, Hurrell RF (1983) J Agric Food Chem 31: 432–437
Lindner W (1988) Indirect separation of enantiomers by liquid chromatography. In: Zief M, Crane LJ (eds) Chromatographic separations. Dekker, New York Basel, pp 91–129
Man EH, Bada JL (1987) Ann Rev Nutr 7: 209–225
Manning JM, Moore S (1968) J Biol Chem 243: 5591–5597
Masters PM, Friedman M (1980) Am Chem Soc Symp Ser 123: 165–194
Matsushima O, Katayama H, Yamada K, Kado Y (1984) Mar Biol Lett 5: 217–225
Nagata Y, Akino T, Ohno K, Kataoka Y, Ueda T, Sakurai T, Shiroshita K-I, Yasuda T (1987) Clin Sci 73: 105–108
Neims AH, Zieverink WD, Smilack JD (1966) J Neurochem 13: 163–168
Palla G, Marchelli R, Dossena A, Casnati G (1989) J Chromatogr 475: 45–53
Preston RL (1987) Comp Biochem Physiol 87B: 55–62
Robinson T (1976) Life Sci 19: 1097–1102
Schleifer KH, Kandler O (1972) Bact Rev 36: 407–477
Scott R (1986) Cheesemaking practice, 2nd edn., Elsevier, London
Tipper DJ, Wright A (1979) The structure and biosynthesis of bacterial cell walls. In: Sokatch JR, Ornston LN (eds) The bacteria, vol. 7. Academic Press, New York, pp 291–426
Tokuhisa S, Saisu K, Naruse K, Yoshikawa H, Baba S (1981) Chem Pharm Bull Jpn 29: 514–518
Tovar RL, Schwass DE (1983) Am Chem Soc Symp Ser 234: 169–185
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Dedicated to Prof. Ernst Bayer, University of Tübingen, on the occasion of his 65th anniversary.
Presented in part at the “2nd International Congress on Amino Acids and Analogues”, Vienna, August 5–9, 1991, and at “Euro Food Chem VI”, September 22–26, 1991, Hamburg.
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Brückner, H., Jaek, P., Langer, M. et al. Liquid chromatographic determination of D-amino acids in cheese and cow milk. Implication of starter cultures, amino acid racemases, and rumen microorganisms on formation, and nutritional considerations. Amino Acids 2, 271–284 (1992). https://doi.org/10.1007/BF00805948
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DOI: https://doi.org/10.1007/BF00805948