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Issue 11, 2008
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Identification of a novel β-replacement reaction in the biosynthesis of 2,3-diaminobutyric acid in peptidylnucleoside mureidomycin A

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Abstract

2,3-Diaminobutyric acid (DABA) is an unusual di-amino acid component of mureidomycin A, a member of the peptidylnucleoside antibiotic family produced by Streptomyces flavidovirens SANK 60486. Radiochemical assays using cell-free extract from S. flavidovirens revealed that 14C-L-Thr is converted into radiolabelled DABA by an ammonia-dependent β-replacement activity, and not via oxidation to 3-keto-2-aminobutyric acid. The substrate specificity of partially purified enzyme was assayed using a spectrophotometric assay, and β-replacement activity was inhibited by known inhibitors of PLP-dependent enzymes. These data imply that DABA is biosynthesised from L-Thr by a PLP-dependent β-replacement enzyme, using ammonia as a nucleophile. These results are consistent with literature proposals for the biosynthesis of 2,3-diaminopropanoic acid from the viomycin biosynthetic gene cluster.

Graphical abstract: Identification of a novel β-replacement reaction in the biosynthesis of 2,3-diaminobutyric acid in peptidylnucleoside mureidomycin A

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Publication details

The article was received on 14 Feb 2008, accepted on 05 Mar 2008 and first published on 07 Apr 2008


Article type: Paper
DOI: 10.1039/B802585A
Org. Biomol. Chem., 2008,6, 1912-1917

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    Identification of a novel β-replacement reaction in the biosynthesis of 2,3-diaminobutyric acid in peptidylnucleoside mureidomycin A

    W. Lam, K. Rychli and T. D. H. Bugg, Org. Biomol. Chem., 2008, 6, 1912
    DOI: 10.1039/B802585A

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