The specificity of amino acid biosynthesis in the Cucurbitaceae

Frisch, David M.; Dunnill, P.; Smith, A.; Fowden, L.

doi:10.1016/s0031-9422(00)86044-6

Cited by 20 publications

(9 citation statements)

References 19 publications

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“…These reactions are thought to proceed in either of two ways: (a) via tryptamine as an intermediate in which decarboxylation of tryptophan takes place first to form tryptamine which is then de-aminated via indolylacetaldehyde to 3-indolylacetic acid or (b) via 3-indolylpyruvic acid in which the de-amination of tryptophan takes place first to form 3-indolylpyruvic acid and then this compound is decarboxylated to form 3-indolylacetic acid. It has been suggested that the enzyme tryptophan synthetase is the enzyme involved in aminotriazoie metabolism (Frisch et al, 1967). Our results indicated that the enzyme preparation from pea buds which was capable of synthesizing tryptophan from indole and serine was able to convert aminotriazoie into its metabolites.…”

Section: Discussionsupporting

confidence: 49%

AMINOTRIAZOLE METABOLISM IN CIRSIUM ARVENSE (L.) SCOP. AND PISUM SATIVUM L.

Smith

Chang

1973

Weed Research

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Summary. Excised leaves as well as intact plants of Canada thistle (Cirsium arvense (L.) Scop.) metabolized 3‐amino‐l,2,4‐triazole (aminotriazole) to three major products, Unknowns II, 1a and 1b. Unknown II was identical to β‐(3‐amino‐l,2,4‐triazolyl‐l‐)α‐alanine. Unknowns 1a and 1b, previously described as one product, were separated by electrophoresis and thin layer chromatography. Unknown 1a appeared to be a metabolic product of Unknown II while Unknown 1B was derived from Unknown 1a. An enzyme preparation from pea (Pisum sativum L. cv. Thompson Laxton) seedlings capable of synthesizing tryptophan from indole and serine was also able to metabolize aminotriazole. Tryptophan synthesis with the enzyme preparation was inhibited by aminotriazole and evidence suggests that aminotriazole metabolism may follow a similar pathway to tryptophan synthesis. Métabolisme de l'aminotriazole chez Cirsium arvense (L.) Scop, et Pisum sativum L.

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Section: Discussionsupporting

confidence: 49%

AMINOTRIAZOLE METABOLISM IN CIRSIUM ARVENSE (L.) SCOP. AND PISUM SATIVUM L.

Smith

Chang

1973

Weed Research

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“…Dunnill and Fowden (1963) have established that the biosynthesis of ,8-pyrazol-l-ylalanine (6) in members of the Cucurbitaceae involves the nucleophile pyrazole reacting with serine. Frisch et al (1967) have shown that a range of plant species and microorganisms (Phaseolus aureus [Leguminales], Chlorella vulgaris, Saccharomyces cerevisiae, and Escherischia coli), have the capacity to convert administered pyrazole to ,8-pyrazol-l-ylalanine (6). Furthermore, Frisch et al (1967) have demonstrated this lack of specificity in Cucumis sativus by the incorporation of a range of synthetic nucleophiles (4-nitropyrazole,I,2,4-triazole, indole, purine, and …”

Section: Discussionmentioning

confidence: 99%

Fluoroacetic acid Biosynthesis: a Proposed Mechanism

Mead¹,

Segal²

1972

Aust. Jnl. Of Bio. Sci.

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A mechanism for the biosynthesis of fluoroacetic acid is presented. This is based on a correlation of phytochemical and taxonomic data together with the established function of pyridoxal phosphate in general amino acid metabolism. Evidence for this hypothesis is based on the reported incorporation of a wide range of synthetic nucleophiles into corresponding j3-substituted alanines by plant homogenates. Fluoride ion is considered to be an acceptable nucleophile for a non-specific enzyme synthesizing a range of j3-substituted alanines, many of which occur in plants elaborating fluoroacetic acid.It is considered that, initially, fluoride is covalently bound to a C3 entity linked to pyridoxal phosphate and which is derived from cysteine, serine, or derivatives. The mechanism for fluoride incorporation is considered to involve direct attack on a carbonium ion but may occur by an exchange process, as nucleophile exchange occurs in j3-substituted alanines in closely related plants.Fluoroacetic acid is considered to be derived from the fluoro-(Ca-pyridoxal phosphate) unit either by (1) transamination and release of fluoropyruvic acid which may produce fluoroacetic acid by an oxidative decarboxylation process, or (2) by decarboxylation, transamination, and hydrolytic release of fluoroacetaldehyde which may be oxidized to fluoroacetic acid.

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“…The Cucurbitaceae contains an assortment of nonprotein amino acids including meta-carboxyphenylalanine, pyrrolidine derivatives, pyrazole-containing compounds and N-substituted derivatives of asparagine (Dunnill & Fowden 1965, Bell 1980, Frisch et al 1967. Some of these are presently useful as taxonomic characters within the family, but may eventually also be significant on a wider scale when related families are chemically investigated.…”

Section: Non-protein Amino Acidsmentioning

confidence: 99%

Secondary metabolites and the higher classification of angiosperms

Gershenzon

Mabry

1983

Nordic Journal of Botany

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The restricted distributions of some classes of secondary metabolites in the angiosperms make them valuable taxonomic characters in assessing systematic relationships at higher levels of classification. Yet, for several reasons, secondary metabolites have not, until recently, been widely used as taxonomic characters above the family level. In this paper, the distributions of a number of classes of secondary compounds are discussed with reference to four recently published systems of higher angiosperm classification: Cronquist's of 1981, Dahlgren's of 1980, Takhtajan's of 1980 and Thome's of 1981. Some of the problems faced in choosing and using secondary metabolite data for systematic purposes (including the effects of our increasing understanding of their functional significance) are covered as well. Among the classes of secondary compounds treated here, benzylisoquinoline alkaloids, iridoids and be–talains are shown to be the most important systematic markers used at present at higher levels of classification, although glucosinolates, polyacetylenes and some other types of alkaloids are also demonstrated to be valuable criteria for making taxonomic judgments above the family rank. In addition, certain terpenoids, flavonoids, phenolics, cyanogenic glycosides and non–protein amino acids are illustrated to be of systematic use in particular cases.

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The specificity of amino acid biosynthesis in the Cucurbitaceae

Cited by 20 publications

References 19 publications

AMINOTRIAZOLE METABOLISM IN CIRSIUM ARVENSE (L.) SCOP. AND PISUM SATIVUM L.

AMINOTRIAZOLE METABOLISM IN CIRSIUM ARVENSE (L.) SCOP. AND PISUM SATIVUM L.

Fluoroacetic acid Biosynthesis: a Proposed Mechanism

Secondary metabolites and the higher classification of angiosperms

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