Literature DB >> 8948453

Synthesis of 3-arsonopyruvate and its interaction with phosphoenolpyruvate mutase.

S Chawla1, E K Mutenda, H B Dixon, S Freeman, A W Smith.   

Abstract

3-Arsonopyruvate was prepared in four steps from glycine. The arsenic-carbon bond was formed by a Meyer reaction between alkaline arsenite and 2-bromo-3-hydroxy-2-(hydroxymethyl)propionic acid; the 3-arsono-2-hydroxy-2-(hydroxymethyl) propionic acid formed was oxidized with periodate to give 3-arsonopyruvate. This proves to be an alternative substrate for phosphoenolpyruvate mutase, giving pyruvate, which was assayed using lactate dehydrogenase. The K(m) is 20 microM, similar to that observed for the natural substrate phosphonopyruvate (17 microM), whereas the kcat. of 0.01 s-1 was much lower than that for phosphonopyruvate (58 s-1). Arsonopyruvate competitively inhibited the action of the mutase on phosphonopyruvate.

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Year:  1995        PMID： 8948453      PMCID： PMC1136813          DOI： 10.1042/bj3080931

Source DB:  PubMed          Journal:  Biochem J        ISSN： 0264-6021            Impact factor:   3.857


  15 in total

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4.  The mechanism of pyrophosphorolysis of RNA by RNA polymerase. Endowment of RNA polymerase with artificial exonuclease activity.

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5.  The arsonomethyl analogue of adenosine 5'-phosphate. An uncoupler of adenylate kinase.

Authors:  S R Adams; M J Sparkes; H B Dixon
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7.  Arsenic mononucleotides. Separation by high-performance liquid chromatography and identification with myokinase and adenylate deaminase.

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Authors:  S J Pollack; S Freeman; D L Pompliano; J R Knowles
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9.  Phosphonate biosynthesis: isolation of the enzyme responsible for the formation of a carbon-phosphorus bond.

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10.  Nucleotide sequence of a carboxyphosphonoenolpyruvate phosphonomutase gene isolated from a bialaphos-producing organism, Streptomyces hygroscopicus, and its expression in Streptomyces lividans.

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  4 in total

Review 1.  Arsenate replacing phosphate: alternative life chemistries and ion promiscuity.

Authors:  Dan S Tawfik; Ronald E Viola
Journal:  Biochemistry       Date:  2011-01-31       Impact factor: 3.162

2.  Arsenite release on enzymic transformation of arsonomethyl substrate analogues: a potentially lethal synthesis by glycerol-3-phosphate dehydrogenase.

Authors:  E K Mutenda; M J Sparkes; H B Dixon
Journal:  Biochem J       Date:  1995-09-15       Impact factor: 3.857

Review 3.  Arsenic binding to proteins.

Authors:  Shengwen Shen; Xing-Fang Li; William R Cullen; Michael Weinfeld; X Chris Le
Journal:  Chem Rev       Date:  2013-06-28       Impact factor: 60.622

4.  Phylogenomic Analysis of Natural Products Biosynthetic Gene Clusters Allows Discovery of Arseno-Organic Metabolites in Model Streptomycetes.

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Journal:  Genome Biol Evol       Date:  2016-07-02       Impact factor: 3.416
  4 in total

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