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Cation of a novel beta-replacement reaction in the biosynthesis of 2,3-diaminobutyric acid in peptidylnucleoside mureidomycin A
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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 ISSN 1477-0520.
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Official URL: http://dx.doi.org/10.1039/b802585a
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 | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Journal or Publication Title: | Organic & Biomolecular Chemistry | ||||
Publisher: | Royal Society of Chemistry | ||||
ISSN: | 1477-0520 | ||||
Official Date: | 2008 | ||||
Dates: |
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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 |
Data sourced from Thomson Reuters' Web of Knowledge
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