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Identification of a novel β-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) 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. 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 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 | ||||
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Subjects: | Q Science > QD Chemistry Q Science > QP Physiology |
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Divisions: | Faculty of Science, Engineering and Medicine > 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 | ||||
Official Date: | 2008 | ||||
Dates: |
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Volume: | Vol.6 | ||||
Number: | No.11 | ||||
Page Range: | pp. 1912-1917 | ||||
DOI: | 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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