Lam, Wai-Ho, Rychli, Kathrin and Bugg, Tim. (2008) Identification of a novel β-replacement reaction in the biosynthesis of 2,3-diaminobutyric acid in peptidylnucleoside mureidomycin A. Organic & Biomolecular Chemistry, Vol.6 (No.11). pp. 1912-1917. ISSN 1477-0520

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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.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry Q Science > QP Physiology
Divisions:	Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH):	Substitution reactions, Butyric acid, Antibiotics, Biosynthesis
Journal or Publication Title:	Organic & Biomolecular Chemistry
Publisher:	Royal Society of Chemistry
ISSN:	1477-0520
Date:	2008
Volume:	Vol.6
Number:	No.11
Page Range:	pp. 1912-1917
Identification Number:	10.1039/b802585a
Status:	Peer Reviewed
Publication Status:	Published
Funder:	Biotechnology and Biological Sciences Research Council (Great Britain) (BBSRC), Erasmus Mundus (Program)
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URI:	http://wrap.warwick.ac.uk/id/eprint/40293

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