Cyanohydrin phosphonate natural product from Streptomyces regensis.
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.
Department of Microbiology and ‡The Institute for Genomic Biology, University of Illinois , Urbana-Champaign, Illinois 61801, United States.
Joel P
JP
Cioni
James R
JR
Doroghazi
Kou-San
KS
Ju
Xiaomin
X
Yu
Bradley S
BS
Evans
Jaeheon
J
Lee
William W
WW
Metcalf
D001483:Base Sequence; D001688:Biological Products / Q000737:chemistry / Q000302:isolation & purification*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry / Q000302:isolation & purification*; D019906:Nuclear Magnetic Resonance, Biomolecular; D063065:Organophosphonates / Q000737:chemistry / Q000302:isolation & purification*; D013302:Streptomyces / Q000737:chemistry / Q000201:enzymology / Q000235:genetics
C000590072:(cyano(hydroxy)methyl)phosphonic acid; D001688:Biological Products; D009570:Nitriles; D063065:Organophosphonates; C430593:cyanohydrin