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Amino Acid 4 Barva.Indd Czech J. Food Sci. Vol. 24, No. 3: 93–109 Biosynthesis of Food Constituents: Amino Acids: 4. Non-protein Amino Acids – a Review JAN VELÍŠEK, ROMAN KUBEC and KAREL CEJPEK Department of Food Chemistry and Analysis, Faculty of Food and Biochemical Technology, Institute of Chemical Technology Prague, Prague, Czech Republic Abstract VELÍŠEK J., KUBEC R., CEJPEK K. (2006): Biosynthesis of food constituents: Amino acids: 4. Non-protein amino acids – a review. Czech J. Food Sci., 24: 93–109. 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-con- taining 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 Plants and microorganisms are able to generate beneficial properties as they exhibit significant all 20 amino acids necessary for the protein syn- antioxidative and anticarcinogenic activities in thesis and they can even synthesise many more animals. In animals, some non-protein amino acids amino acids. For example, more than 700 of non- act in intracellular metabolic processes (e.g. in the protein amino acids have been isolated from plants metabolism of lipids), as macroergic substrates, as secondary metabolites. Some of these amino and neurotransmitters, and intermediates in the acids appear to play an important role as interme- synthesis of some biologically active compounds diates in the biosynthesis of the plant signalling (e.g. hormones) and stimulants. molecules, vitamins, and other constituents (e.g. alkaloids, bile salts, and pigments). They repre- 1 3-AMINO ACIDS AND 4-AMINO ACIDS sent storage forms of nitrogen or sulfur, some of them play a role in the enhancement of tolerance β-Alanine (3-aminopropanoic acid) is involved against abiotic stress, some act in the plant chemi- in the biosynthesis of pantothenic acid, coen- cal defence system against a variety of organisms zyme A (HS-CoA), and some histidine dipeptides as they manifest antimetabolic effects in viruses, (VELÍŠEK et al. 2006). The principal pathway of bacteria, fungi, as well as in lower and higher β-alanine formation (KEGG) is the decarboxyla- plants and animals. Many of these amino acids tion of L-aspartic acid catalysed by the pyridoxal are, however, considered to be only biochemical 5´-phosphate protein aspartate-1-decarboxylase oddities. Some of these amino acids also show (EC 4.1.1.11) (Figure 1). Partly supported by the Ministry of Education, Youth and Sports of the Czech Republic, Project No. MSM 6046137305. 93 Vol. 24, No. 3: 93–109 Czech J. Food Sci. CO2 CO2 COOH HOOC COOH HOOC NH2 HOOC HOOC NH2 NH2 NH2 EC 4.1.1.11 EC 4.1.1.15 L-aspartic acid �-alanine L-glutamic acid 4-aminobutanoic acid Figure 1 Figure 2 γ-Aminobutanoic acid (GABA, 4-aminobuta- methionine/S-adenosylhomocysteine ratio rather noic acid) acts as a chemical messenger in the than to synthesise sarcosine2 (KEGG). cell communication. It predominantly occurs in Glycine betaine (N,N,N-trimethylglycine, tri- the brain tissue (but also in plant and microbial methylammoniumacetobetaine) is produced by cells) where it acts as a neurotransmitter inhibi- certain higher plants and bacteria. It is synthesised tor. It is also a constituent of some peptides, e.g. at elevated rates in response to various types of nisine. γ-Aminobutanoic acid is predominantly environmental stress via two distinct pathways: formed by decarboxylation of L-glutamic acid oxidation of choline, or N-methylation of glycine catalysed by the pyridoxal 5´-phosphate protein, i.e. (CHEN & MURATA 2002). For almost all biological glutamate decarboxylase (EC 4.1.1.15) (Figure 2) systems, including most animals, plants (e.g. plants (KEGG). of the family Chenopodiaceae, such as spinach), and microorganisms, glycine betaine biosynthesis is 2 N-SUBSTITUTED AMINO ACIDS accomplished in chloroplasts by the first pathway, conversion of choline via the unstable interme- 2.1 Sarcosine and glycine betaine diate betaine aldehyde (JAIN & SELVARAJ 2000). The first step of choline oxidation is catalysed by 1 Glycine N-methyltransferase (EC 2.1.1.20) ca- ferredoxin-dependent choline monooxygenase talyses the transfer of the methyl group of S-ade- (EC 1.14.15.7), and the second one by NAD(P)- nosyl-methionine (SAM or AdoMet) to glycine dependent betaine aldehyde dehydrogenase to form S-adenosylhomocysteine (AdoHcy) and (EC 1.2.1.8)3 (Figure 4). N-methylglycine (sarcosine, Figure 3). The enzyme is unique among methyltransferases since the 2.2 Carnitine methylated product has no physiological activity. It has been suggested that the major role of glycine L-Carnitine [3-hydroxy-4-(N,N,N-trimethyl)- N-methyltransferase is to regulate the S-adenosyl- aminobutyric acid] is required for the transfer of ac- 1In addition to its enzymatic role, glycine N-methyltransferase has been shown to be a major folate binding protein in the rat liver cytosol, to be a polycyclic aromatic hydrocarbon-binding protein and a mediator of cytochrome P4501A1 gene expression. 2Sarcosine is also formed as a product of choline and creatine catabolism. Both compounds have several metabolic fates. Choline may be converted into acetylcholine, to phosphatidylcholine or to N,N-dimethylglycine, which is then converted to sarcosine and ultimately to glycine. Dimethylglycine dehydrogenase (EC 1.5.99.2) is an enzyme cataly- sing the oxidative demethylation of N,N-dimethylglycine to form sarcosine. Subsequently, sarcosine dehydrogenase (EC 1.5.99.1) converts sarcosine into glycine. Hydrolysis of creatine by creatinase (EC 3.5.3.3) yields sarcosine and urea. The product of creatinine hydrolysis by creatinine deamidase (EC 3.5.4.21), N-methylhydantoin, yields N-car- bamoylsarcosine by the catalysis of N-methylhydantoinase (ATP-hydrolysing) (EC 3.5.2.14). 3Bacteria Escherichia coli also form glycine betaine from choline but do not use choline monooxygenase (EC 1.14.15.7) as they have choline dehydrogenase (EC 1.1.99.1) instead that generates hydrogen peroxide. Glycine betaine bio- synthesis in the microorganisms Arthrobacter globiformis requires only one enzyme choline oxidase (EC 1.1.3.17). Recently, a novel pathway of glycine betaine biosynthesis from glycine via sarcosine (glycine N-methyltransferase, EC 2.1.1.20) and N,N-dimethylglycine was found in two extremely halophilic microorganisms Ascinopolyspora halo- philia and Ectothiorhodospira halochloris. 94 Czech J. Food Sci. Vol. 24, No. 3: 93–109 H3C S Ad S Ad COOH COOH + + + H NH2 NH2 HN NH2 EC 2.1.1.20 CH COOH 3 COOH glycine S-adenosyl-L-methionine sarcosine S-adenosyl-L-homocysteine Figure 3 ferredoxin (reduced) + O2 ferredoxin (oxidized) + 2 H2O NAD(P) + H2O NAD(P)H + H (H C) N (H3C)3N CH2OH 3 3 CHO (H3C)3N COOH EC 1.14.15.7 EC 1.2.1.8 choline betaine aldehyde glycine betaine Figure 4 tivated acyl groups across intracellular membranes. obutyraldehyde] by the pyridoxal 5´-phosphoric acid Many organisms, ranging from bacteria to mam- protein β-hydroxy-ε-(N-trimethyl)lysine aldolase mals, are able to synthesise carnitine from lysine (EC 2.1.2.1). 4-(N,N,N-trimethyl)aminobutanal and methionine. Lysine becomes available in the is subsequently oxidised by NAD(P)-dependent form of ε-(N,N,N-trimethyl)lysine after lysosomal 4-trimethylaminobutyraldehyde dehydrogenase hydrolysis of proteins that contain this amino acid (EC 1.2.1.47) or aldehyde dehydrogenase (NAD+) (EC as a result of the post-translational methylation 1.2.1.3) to form 4-(N,N,N-trimethyl)aminobutanoic of lysine residues by lysine N-methyltransferase acid (γ-butyrobetaine). Finally, 4-(N,N,N-tri- (EC 2.1.1.43), using SAM as the methyl donor. methylaminobutanoic acid is hydroxylated at the In the first step of the carnitine biosynthe- C-3 position by γ-butyrobetaine hydroxylase sis, ε-(N,N,N-trimethyl)lysine is hydroxylated (EC 1.14.11.1) to form carnitine (Figure 5). Like to β-hydroxy-ε-(N,N,N-trimethyl)lysine [3-hy- lysyl hydroxylase (EC 1.14.11.4, VELÍŠEK & CEJPEK droxy-ε-(N,N,N-trimethyl)lysine] by trimethyl- 2006), trimethyllysine dioxygenase and 4-trimethyl- lysine dioxygenase (EC 1.14.11.8). Subsequently, aminobutyraldehyde dehydrogenase are non-heme β-hydroxy-ε-(N,N,N-trimethyl)lysine is cleaved ferrous-iron dioxygenases that require 2-oxoglu- by retroaldolisation into glycine and 4-(N,N,N- taric acid and molecular oxygen as substrates, and trimethyl)aminobutanal [γ-(N,N,N-trimethyl)amin Fe2+ and L-ascorbic acid (for regeneration of Fe2+ COOH NH2 glycine 2-oxoglutaric acid + O2 succinic acid + CO 2 OH (H3C)3N COOH (H3C)3N COOH (H3C)3N CHO NH2 EC 1.14.11.8 NH2 EC 2.1.2.1 �-(N,N,N-trimethyl)-L-lysine 3-hydroxy-�-(N,N,N-trimethyl)-L-lysine 4-(N,N,N-trimethyl)aminobutanal NAD(P) EC 1.2.1.3 EC 1.2.1.47 NAD(P)H + H succinic acid + CO2 2-oxoglutaric acid + O2 OH (H3C)3N COOH (H3C)3N COOH EC 1.14.11.1 L-carnitine 4-(N,N,N-trimethyl)aminobutanoic acid Figure 5 95 Vol. 24, No. 3: 93–109 Czech J. Food Sci. ions) as cofactors (VAZ et al. 1998; SWIEGERS et proceeds via unstable N-hydroxy-1-aminocyclo- al. 2002). propane-1-carboxylic acid, which breaks down into ethylene (derived from the C-2 and C-3 carbons 3 ALICYCLIC AMINO ACIDS of 1-aminocyclopropane-1-carboxylic acid) and cyanoformic acid.
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