Lam, Wai-Ho, Rychli, Kathrin and Bugg, Tim (2008) Cation of a novel beta-replacement reaction in the biosynthesis of 2,3-diaminobutyric acid in peptidylnucleoside mureidomycin A. Organic & Biomolecular Chemistry, Vol.6 (No.11). pp. 1912-1917. doi:10.1039/b802585a

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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 C-14-L-Thr is converted into radiolabelled DABA by an ammonia-dependent beta-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 beta-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 beta-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
Divisions:	Faculty of Science > Chemistry
Journal or Publication Title:	Organic & Biomolecular Chemistry
Publisher:	Royal Society of Chemistry
ISSN:	1477-0520
Official Date:	2008
Dates:	Date Event 2008 Published
Volume:	Vol.6
Number:	No.11
Number of Pages:	6
Page Range:	pp. 1912-1917
DOI:	10.1039/b802585a
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access

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