Czech J. Food Sci., 2006, 24(3):93-109 | DOI: 10.17221/3304-CJFS

Biosynthesis of food constituents: Amino acids: 4. Non-protein amino acids - a review

Jan Velíšek, Roman Kubec, Karel Cejpek
Department of Food Chemistry and Analysis, Faculty of Food and Biochemical Technology, Institute of Chemical Technology Prague, Prague, Czech Republic

This review article gives a brief survey of the principal pathways that lead to the biosynthesis of the most important non-protein amino acids occurring in foods and feeds. These amino acids have been divided into the following groups: 3-amino acids and 4-amino acids, N-substituted amino acids, alicyclic amino acids, hydroxyamino acids, sulfur-containing amino acids, basic amino acids, and taurine.

Keywords: biosynthesis; 3-amino acids; 4-amino acids; N-substituted amino acids; alicyclic amino acids; hydroxyamino acids; sulfur-containing amino acids; basic amino acids; taurine

Published: June 30, 2006  Show citation

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Velíšek J, Kubec R, Cejpek K. Biosynthesis of food constituents: Amino acids: 4. Non-protein amino acids - a review. Czech J. Food Sci. 2006;24(3):93-109. doi: 10.17221/3304-CJFS.
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References

  1. BARLOW J.N., ZHANG Z., JOHN P., BALDWIN J.E., SCHOFIELD C.J. (1997): Inactivation of 1-aminocyclopropane1-carboxylate oxidase involves oxidative modifications. Biochemistry, 36: 3563-3569. Go to original source... Go to PubMed...
  2. BLAKE O.A., JACKSON J.C., JACKSON M.A., GORDON C.L.A. (2004): Assessment of dietary exposure to the natural toxin hypoglycin in ackee (Blighia sapida) in Jamaican consumers. Food Research International, 37: 833-838. Go to original source...
  3. BLOCK E. (1992): The organosulfur chemistry of the genus Allium-implications for the organic chemistry of sulfur. Angewandte Chemie, Int. Ed. Engl., 31: 1135-1178. Go to original source...
  4. CHARNG Y.-Y., CHOU S.-J., JIAANG W.-T., CHEN S.-T., YANG S.F. (2001): The catalytic mechanism of 1-aminocyclopropane-1-carboxylic acid oxidase. Archives of Biochemistry and Biophysics, 385: 179-185. Go to original source... Go to PubMed...
  5. CHEN T.H.H., MURATA N. (2002): Enhancement of tolerance of abiotic stress by metabolic engineering of betaines and other compatible solutes. Current Opinion in Plant Biology, 5: 250-257. Go to original source... Go to PubMed...
  6. DO K.Q., TAPPAZ M.L. (1996): Specificity of cysteine sulfinate decarboxylase (CSD) for sulphur-containing aminoacids. Neurochemistry International, 28: 363-371. Go to original source... Go to PubMed...
  7. EPPER B., DAWSON R., Jr. (2001): Dietary taurine manipulations in aged male Fischer 344 rat tissue: taurine concentration, taurine biosynthesis, and oxidative markers. Biochemical Pharmacology, 62: 29-39. Go to original source... Go to PubMed...
  8. GAKIERE B., DENIS L., DROUX M., JOB D. (2002): Overexpression of cystathionine γ-synthase in Arabidopsis thaliana leads to increased levels of methionine and S-methylmethionine. Plant Physiology and Biochemistry, 40: 119-126. Go to original source...
  9. HENRY S.H., PAGE S.W., BOLGER P.M. (1998): Hazard assessment of ackee fruit (Blighia sapida). Human and Ecological Risk Assessment, 4: 1175-1187. Go to original source...
  10. IKEGAMI F., HORIUCHI S., KOBORI M., MORISHIGE I., MURAKOSHI I. (1992): Biosynthesis of neuroactive amino acids by cysteine synthases in Lathyrus latifolius. Phytochemistry, 31: 1991-1996. Go to original source...
  11. IKEGAMI F., MURAKOSHI I. (1999): Enzymic synthesis of non-protein β-substituted alanines and some higher homologues in plants. Phytochemistry, 35: 1089-1104. Go to original source...
  12. IMAI S., TSUGE N., TOMOTAKE M., NAGATOME Y., SAWADA H., NAGATA T., KUMAGAI H. (2002): An onion enzyme that makes the eyes water. Nature, 419: 685. Go to original source... Go to PubMed...
  13. IUBMB (2003): http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/.
  14. JAIN R.K., SELVARAJ G. (2000): Choline import into chloroplasts limits glycine betaine synthesis in tobacco: analysis of plants engineered with a chloroplastic or a cytosolic pathway. Metabolic Engineering, 2: 300-311. Go to original source... Go to PubMed...
  15. JANG M.H., JUN D.Y., RUE S.W., HAN K.H., PARK W., KIM Y.H. (2002): Arginine antimetabolite L-canavanine induces apoptotic cell death in human Jurkat T cells via caspase-3 activation regulated by Bcl-2 or Bcl-xL. Biochemical and Biophysical Research Communications, 295: 283-288. Go to original source... Go to PubMed...
  16. JONES M.G., HUGHES J., TREGOVA A., MILNE J., TOMSETT A.B., COLLIN H.A. (2004): Biosynthesis of the flavour precursors in onion and garlic. Journal of Experimental Botany, 55: 1903-1918. Go to original source... Go to PubMed...
  17. KAISAKIA P.A., JERKINS A.A., GOODSPEED D.C., STEELE R.D. (1995): Cloning and characterization of rat cysteine sulfinic acid decarboxylase. Biochimica et Biophysica Acta, 1262: 79-82. Go to original source... Go to PubMed...
  18. KAYA K., SANO T. (1991): Definition of total biosynthesis pathway of taurolipids in Tetrahymena cells. Biochimica et Biophysica Acta, 1084: 101-104. Go to original source... Go to PubMed...
  19. KEAN E.A. (1989): Hypoglycin. In Toxicants of plant origin. Vol. III. In: CHEEKE P.R. (ed.): Proteins and Amino Acids. CRC Press, Inc., Boca Raton: 229-262.
  20. KEAN E.A., LEWIS C.E. (1981): Biosynthesis of L-β-(methylenecyclopropyl)-alanine (hypoglycin) in Blighia sapida. Phytochemistry, 20: 2161-2164. Go to original source...
  21. KEGG: Kyoto Encyclopedia of Genes and Genomes, http://www.biologie.uni-hamburg.de.
  22. KLAIR S.S., MOHAN H.R., KITAHARA T. (1998): A novel synthetic approach towards phytosiderophores: expeditious synthesis of nicotianamine and 2´-deoxymugineic acid. Tetrahedron Letters, 39: 89-92. Go to original source...
  23. KUBEC R., KIM S., MCKEON D.M., MUSAH R.A. (2002): Isolation of S-n-butylcysteine sulfoxide and six n-butyl-containing thiosulfinates from Allium siculum. Journal of Natural Products, 65: 960-964. Go to original source... Go to PubMed...
  24. KUBEC R., SVOBODOVÁ M., VELÍŠEK J. (2000): Distribution of S-alk(en)ylcysteine sulfoxides in some Allium species. Identification of a new flavor precursor: S-ethylcysteine sulfoxide (ethiin). Journal of Agricultural and Food Chemistry, 48: 428-433. Go to original source... Go to PubMed...
  25. KUO Y.-H., LAMBEIN F. (1991): Biosynthesis of the neurotoxin β-N-oxalyl-α,β-diaminopropionic acid in callus tissue of Lathyrus sativus. Phytochemistry, 30: 3241-3244. Go to original source...
  26. LANCASTER J.E., SHAW M.L. (1989): γ-Glutamyl peptides in the biosynthesis of S-alk(en)yl-L-cysteine sulfoxides (flavour precursors) in Allium. Phytochemistry, 28: 455-460. Go to original source...
  27. LARSEN M., TRAPP S., PIRANDELLO A. (2004): Removal of cyanide by woody plants. Chemosphere, 54, 325-333. Cited in: MEYER J.J.M., GROBBELAAR N. (eds.) (1986): Biosynthesis of pipecolic acid and 4-hydroxypipecolic acid. Phytochemistry, 25: 1469-1470. Go to original source...
  28. LEE Y., KWON Y.M. (2000): Identification of an isoform of ornithine carbamoyltransferase that can effectively utilize canaline as a substrate from the leaves of Canavalia lineata. Plant Science, 151: 145-151. Go to original source... Go to PubMed...
  29. LEE Y., LEE C.B., KIM S.-G., KWON Y.M. (1997): Purification and characterization of ornithine carbamoyltransferase from the chloroplasts of Canavalia lineata leaves. Plant Science, 122: 217-224. Go to original source...
  30. LOMBARDINI J.B. (1991): Taurine: retinal function. Brain Research Reviews, 16: 151-169. Go to original source... Go to PubMed...
  31. MEYER J.J.M., GROBBELAAR N. (eds.) (1986): Biosynthesis of pipecolic acid and 4-hydroxypipecolic acid. Phytochemistry, 25: 1469-1470. Go to original source...
  32. MORI S. (1994): Iron acquisition by plants. Current Opinion in Plant Biology, 2, 250-253. Go to original source... Go to PubMed...
  33. MORTON T.C. (1998): Chemotaxonomic significance of hydroxylated pipecolic acids in Central American Inga (Fabaceae: Mimosoideae: Ingeae). Biochemical Systematics and Ecology, 26: 379-401. Go to original source...
  34. NATALINI B., CAPODIFERRO V., DE LUCA C., ESPINAL R. (2000): Isolation of pure (2S,1´S,2´S)-2(2´-carboxycyclopropyl)glycine from Blighia sapida (akee). Journal of Chromatography A, 873: 283-286. Go to original source... Go to PubMed...
  35. NATELSON S., KOLLER A., TSENG H.Y., DODS R.F. (1977): Canaline carbamoyltransferase in human liver as part of a metabolic cycle in which guanidino compounds are formed. Clinical Chemistry, 23: 960-966. Go to original source...
  36. PARK E., PARK S.Y., WANG C., XU J., LAFAUCI G., SCHULLER-LEVIS G. (2002): Cloning of murine cysteine sulfinic acid decarboxylase and its mRNA expression in murine tissues. Biochimica et Biophysica Acta, 1574: 403-406. Go to original source... Go to PubMed...
  37. PARRY R.J., SOOD G.R. (1985): Investigations of the biosynthesis of trans-(+)-S-1-propenyl-L-cysteine sulfoxide in onions (Allium cepa). Journal of the American Chemical Society, 111: 4514-4515. Go to original source...
  38. ROSENTHAL G.A. (1991): The biochemical basis for the deleterious effects of L-canavanine. Phytochemistry, 30: 1055-1058. Go to original source...
  39. ROSENTHAL G.A. (1997): L-Canaline: a potent antimetabolite and anti-cancer agent from leguminous plants. Life Science, 60: 1635-1641. Go to original source... Go to PubMed...
  40. SCHULLER-LEVIS G.B., PARK E. (2003): Taurine: new implications for an old amino acid. FEMS Microbiological Letters, 226: 195-202. Go to original source... Go to PubMed...
  41. SHERRATT H.S.A. (1986): Hypoglycin, the famous toxin of the unripe Jamaican ackee fruit. Trends Pharmacological Science, 7: 186-191. Go to original source...
  42. STEFELS J. (2000): Physiological aspects of the production and conversion of DMSP in marine algae and higher plants. Journal of Sea Research, 43: 183-197. Go to original source...
  43. SUGII M., MIURA H., NAGATA K. (1981): 3-Isoxazolidone from Jack been seedlings. Phytochemistry, 20: 451-453. Go to original source...
  44. SWIEGERS J.H., VAZ F.M., PRETORIUS I.S., WANDERS R.J.A., BAUER F.F. (2002): Carnitine biosynthesis in Neurospora crassa: identification of a cDNA coding for ε-N-trimethyllysine hydroxylase and its functional expression in Saccharomyces cerevisiae. FEMS Microbiological Letters, 210: 19-23. Go to original source...
  45. VAZ F.M., VAN GOOL S., OFMAN R., IJLST L., WANDERS R.J.A. (1998): Carnitine biosynthesis: identification of the cDNA encoding human γ-butyrobetaine hydroxylase. Biochemical and Biophysical Research Communications, 250: 506-510. Go to original source... Go to PubMed...
  46. VELÍŠEK J. (2002): Chemie potravin. 2. vydání. Ossis, Tábor.
  47. VELÍŠEK J., CEJPEK K. (2006): Biosynthesis of food constituents: Amino acids: 1. The glutamic acid and aspartic acid group - a review. Czech Journal of Food Sciences, 24: 1-10. Go to original source...
  48. VELÍŠEK J., KUBEC R., CEJPEK K. (2006): Biosynthesis of food constituents: Peptides - a review. Czech Journal of Food Sciences, 24: in press. Go to original source...
  49. YIGZAW Y., LARRSON N., GORTON L., RUZGAS T., SOLOMON T. (2001): Liquid chromatographic determination of total and β-N-oxalyl-L-α,β-diaminopropionic acid in Lathyrus sativus seeds using both refractive index and bioelectrochemical detection. Journal of Chromatography A, 929: 13-21. Go to original source... Go to PubMed...

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