Cyanohydrin phosphonate natural product from Streptomyces regensis
| Autor: | Joel P. Cioni, Kou San Ju, Jaeheon Lee, Xiaomin Yu, Bradley S. Evans, William W. Metcalf, James R. Doroghazi |
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| Rok vydání: | 2014 |
| Předmět: |
Stereochemistry
Molecular Sequence Data Organophosphonates Pharmaceutical Science Biology 01 natural sciences Streptomyces Article Analytical Chemistry 03 medical and health sciences chemistry.chemical_compound Drug Discovery Gene cluster Nitriles Organic chemistry Nuclear Magnetic Resonance Biomolecular Cyanohydrin 030304 developmental biology Pharmacology 0303 health sciences Biological Products Natural product Base Sequence Molecular Structure 010405 organic chemistry Organic Chemistry biology.organism_classification Phosphonate 0104 chemical sciences Metabolic pathway Complementary and alternative medicine chemistry Molecular Medicine Streptomyces regensis |
| Zdroj: | Journal of Natural Products |
| ISSN: | 1520-6025 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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