Identification of a novel β-replacement reaction in the biosynthesis of 2,3-diaminobutyric acid in peptidylnucleoside mureidomycin A
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 1477-0520Full text not available from this repository.
Official URL: http://dx.doi.org/10.1039/B802585A
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|
|Page Range:||pp. 1912-1917|
|Funder:||Biotechnology and Biological Sciences Research Council (Great Britain) (BBSRC), Erasmus Mundus (Program)|
1 K. I. Kimura and T. D. H. Bugg, Nat. Prod. Rep., 2000, 20, 252.
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