Issue 11, 2008
From the journal:

Organic & Biomolecular Chemistry

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

Wai-Ho Lam,a   Kathrin Rychlia  and  Timothy D. H. Bugg*a  

* Corresponding authors

a University of Warwick, Department of Chemistry, Coventry, United Kingdom

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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Article information

DOI
https://doi.org/10.1039/B802585A
Article type
Paper
Submitted
14 Feb 2008
Accepted
05 Mar 2008
First published
07 Apr 2008

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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