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Cyanohydrin Phosphonate Natural Product from Streptomyces regensis.
MedLine Citation:
PMID:  24437999     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Streptomyces regensis strain WC-3744 was identified as a potential phosphonic acid producer in a large-scale screen of microorganisms for the presence of the pepM gene, which encodes the key phosphonate biosynthetic enzyme phosphoenolpyruvate phosphonomutase. (31)P NMR revealed the presence of several unidentified phosphonates in spent medium after growth of S. regensis. These compounds were purified and structurally characterized via extensive 1D and 2D NMR spectroscopic and mass spectrometric analyses. Three new phosphonic acid metabolites, whose structures were confirmed by comparison to chemically synthesized standards, were observed: (2-acetamidoethyl)phosphonic acid (1), (2-acetamido-1-hydroxyethyl)phosphonic (3), and a novel cyanohydrin-containing phosphonate, (cyano(hydroxy)methyl)phosphonic acid (4). The gene cluster responsible for synthesis of these molecules was also identified from the draft genome sequence of S. regensis, laying the groundwork for future investigations into the metabolic pathway leading to this unusual natural product.
Authors:
Joel P Cioni; James R Doroghazi; Kou-San Ju; Xiaomin Yu; Bradley S Evans; Jaeheon Lee; William W Metcalf
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2014-1-17
Journal Detail:
Title:  Journal of natural products     Volume:  -     ISSN:  1520-6025     ISO Abbreviation:  J. Nat. Prod.     Publication Date:  2014 Jan 
Date Detail:
Created Date:  2014-1-20     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7906882     Medline TA:  J Nat Prod     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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