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
- 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
References
- 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...
- 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...
- 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...
- 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...
- 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...
- 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...
- 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...
- 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...
- 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...
- 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...
- 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...
- 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...
- IUBMB (2003): http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/.
- 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...
- 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...
- 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...
- 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...
- 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...
- 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.
- 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...
- KEGG: Kyoto Encyclopedia of Genes and Genomes, http://www.biologie.uni-hamburg.de.
- 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...
- 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...
- 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...
- 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...
- 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...
- 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...
- 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...
- 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...
- LOMBARDINI J.B. (1991): Taurine: retinal function. Brain Research Reviews, 16: 151-169.
Go to original source...
Go to PubMed...
- MEYER J.J.M., GROBBELAAR N. (eds.) (1986): Biosynthesis of pipecolic acid and 4-hydroxypipecolic acid. Phytochemistry, 25: 1469-1470.
Go to original source...
- MORI S. (1994): Iron acquisition by plants. Current Opinion in Plant Biology, 2, 250-253.
Go to original source...
Go to PubMed...
- 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...
- 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...
- 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...
- 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...
- 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...
- ROSENTHAL G.A. (1991): The biochemical basis for the deleterious effects of L-canavanine. Phytochemistry, 30: 1055-1058.
Go to original source...
- 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...
- 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...
- 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...
- 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...
- SUGII M., MIURA H., NAGATA K. (1981): 3-Isoxazolidone from Jack been seedlings. Phytochemistry, 20: 451-453.
Go to original source...
- 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...
- 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...
- VELÍŠEK J. (2002): Chemie potravin. 2. vydání. Ossis, Tábor.
- 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...
- 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...
- 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...
This is an open access article distributed under the terms of the Creative Commons Attribution-NonCommercial 4.0 International (CC BY NC 4.0), which permits non-comercial use, distribution, and reproduction in any medium, provided the original publication is properly cited. No use, distribution or reproduction is permitted which does not comply with these terms.