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

Velı́šek, J.; Kubec, Roman; Cejpek, Karel

doi:10.17221/3304-cjfs

Cited by 22 publications

(11 citation statements)

References 45 publications

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“…Hydroxytryptophan is also naturally produced by insects and mammals from the essential amino acid, tryptophan (Murch et al 2000). Pipecolic acid (a secondary defence compound) also occurs in animals where it acts as a stimulant of GABA receptors (Or and Ward 2004;Velisek et al 2006). Mimosine was found in seeds, leaves and in root exudates of Mimosa pudica or Leucaena leucocephala (Xuan et al 2006).…”

Section: Npaas With Cyclic and Heterocyclic Skeletonsmentioning

confidence: 99%

Non-protein amino acids: plant, soil and ecosystem interactions

et al. 2010

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Non-protein amino acids are a significant store of organic nitrogen in many ecosystems, but there is a lack of knowledge relating to them. Research has indicated that they play important roles as metabolites, as allelopthic chemicals, in nutrient acquisition, in signalling and in stress response. They are also thought to be responsible for significant medical issues in both invertebrate and vertebrate animals. This review attempts to appraise the literature related to non-protein amino acids, both in terms of their metabolism, plant-soil interactions and at the level of the ecosystem, where they are seen as significant drivers of structure and function. Finally, important areas for future research are discussed.

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Section: Npaas With Cyclic and Heterocyclic Skeletonsmentioning

confidence: 99%

Non-protein amino acids: plant, soil and ecosystem interactions

et al. 2010

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“…Although γ-glutamyl peptides are well represented in many organisms, their roles and properties are often not well understood yet (VELÍŠEK 2002;VELÍŠEK et al 2005). In some cases, plant γ-glutamyl peptides play a role in the transport of amino acids across the membranes, protect plant cells (phytochelatins) against phytotoxic heavy metals, or they may function as storage compounds of nitrogen and sulfur (in Allium and Brassica species), and may also represent a significant pool of bioactive organoselenium compounds (LANCASTER & SHAW 1989, 1991SHAW et al 2005).…”

Section: Other γ-Glutamyl Peptidesmentioning

confidence: 99%

“…Nine of these peptides occur as intermediates in the biosynthesis of S-alk(en)ylcysteine sulfoxides (VELÍŠEK et al 2005), including γ-glutamyl-S-allylcysteine sulfoxide in garlic. (E)-γ-Glutamyl-S-(prop-1-en-1-yl)cysteine sulfoxide and S-(2-carboxypropyl)glutathione occur in onion (Figure 3).…”

Section: Other γ-Glutamyl Peptidesmentioning

confidence: 99%

“…Such γ-glutamyl peptides may be formed by the reaction of GSH with the ethylene precursor, i.e. 1-aminocyclopropane-1-carboxylic acid, in tomato (MARTIN & SLOVIN 2000) and hypoglycin A in the ackee fruit, respectively (VELÍŠEK et al 2005).…”

Section: Other γ-Glutamyl Peptidesmentioning

confidence: 99%

“…One of two possible biosynthetic pathways leading to S-alk(en)ylcysteine sulfoxides in Allium vegetables (VELÍŠEK et al 2005) proceeds via S-alk(en)ylation of the cysteine in glutathione (GSH), followed by transpeptidation to remove the glycyl moiety, oxidation to cysteine sulfoxide by oxidases, and finally a removal of the glutamyl O group to yield S-alk(en)ylcysteine sulfoxide. Alternatively, S-alk(en)ylcysteines may also be formed by the removal of the glutamic acid moiety from the dipeptide.…”

Section: Other γ-Glutamyl Peptidesmentioning

confidence: 99%

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Biosynthesis of food constituents: Peptides - a review

Velidek¹,

Kubec²,

Cejpek³

2006

Czech J. Food Sci.

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Peptides display a wide variety of biological functions and many of them have remarkable physiological properties. Some are widely distributed in nature and found in many different organisms, whereas others are only of a restricted occurrence. For example, peptides function as neurotransmitters and hormones and thus control many physiological processes. Furthermore, the toxic principles of some plants and mushrooms, insect, snake, and spider venoms are usually peptides.Peptides are biosynthesised by ribosomal and nonribosomal (multi-functional enzyme) processes from a wide range of amino acids. Ribosomal peptide biosynthesis leads to enzymes, peptide hormones, and many other physiologically active peptides. Nonribosomal peptide biosynthesis is responsible for the formation of glutathione, histidine-containing dipeptides of skeletal muscles, peptide toxins, and peptide antibiotics. The mechanisms of these processes are, however, beyond the scope of this review.Many structures biosynthesised by ribosomal processes are additionally modified. Glycopeptides are produced by adding sugar residues via O-glycoside linkages to the hydroxyls of serine and threonine residues or via N-glycoside linkages to the amino group of asparagine. Phosphopeptides and phosphoproteins have the hydroxyl group of serine or threonine esterified with phosphoric acid. Many peptides contain a pyroglutamic (glutiminic) acid residue at the N-terminus, which is a consequence of glutamic acid intramolecular cyclisation between the γ-carboxyl and the α-amino group. The C-terminal carboxylic acids may also frequently be converted to an amide.Nonribosomal processes synthesise many natural peptides occurring in foods. These peptides are formed by a sequence of enzyme-controlled reactions. During these processes, each amino acid (often not encoded by DNA) is added (after activation by conversion into AMP esters) as a result of the specificity of the enzyme involved. This review article gives a brief survey of principal pathways that lead to the biosynthesis of most important peptides occurring in foods. Glutathione, selected plant γ-glutamyl peptides, and animal histidine dipeptides are included in this review. Biosynthesis of Food

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Significance of the Natural Occurrence of L‐ Versus D‐Pipecolic Acid: A Review

et al. 2013

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Pipecolic acid naturally occurs in microorganisms, plants, and animals, where it plays many roles, including the interactions between these organisms, and is a key constituent of many natural and synthetic bioactive molecules. This article provides a review of current knowledge on the natural occurrence of pipecolic acid and the known and potential significance of its L- and D-enantiomers in different scientific disciplines. Knowledge gaps with perspectives for future research identified within this article include the roles of the L- versus the D-enantiomer of pipecolic acid in plant resistance, nutrient acquisition, and decontamination of polluted soils, as well as rhizosphere ecology and medical issues.

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

Cited by 22 publications

References 45 publications

Non-protein amino acids: plant, soil and ecosystem interactions

Non-protein amino acids: plant, soil and ecosystem interactions

Biosynthesis of food constituents: Peptides - a review

Significance of the Natural Occurrence of L‐ Versus D‐Pipecolic Acid: A Review

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