Characterization of the epoxide hydrolase NcsF2 from the neocarzinostatin biosynthetic gene cluster.
Neocarzinostatin (1) biosynthesis is proposed to involve a vicinal diol intermediate. It is reported that NcsF2, one of two epoxide hydrolases encoded by the NCS gene cluster, catalyzes regiospecific addition of H(2)O to C-2 of both (R)- and (S)-styrene oxides to afford (R)- and (S)-1-phenyl-1,2-ethanediols, respectively, supporting its proposed role in 1 biosynthesis. (R)-1-Phenyl-1,2-ethanediol (87% yield and 99% ee) was obtained from (+/-)-styrene oxide hydrolysis by cocatalysis using NcsF2 and SgcF, the complementary epoxide hydrolase from the C-1027 biosynthetic pathway.
Lin
Shuangjun
S
Division of Pharmaceutical Sciences, University of Wisconsin-Madison, Madison, Wisconsin 53705, USA.
Horsman
Geoffrey P
GP
Shen
Ben
B
D002384:Catalysis; D004851:Epoxide Hydrolases / Q000235:genetics / Q000378:metabolism*; D004852:Epoxy Compounds / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry / Q000201:enzymology / Q000235:genetics; D009353:Zinostatin / Q000138:chemical synthesis* / Q000737:chemistry
D004852:Epoxy Compounds; D009353:Zinostatin; C013690:styrene oxide; D004851:Epoxide Hydrolases; C553700:epoxide hydrolase NcsF2, Streptomyces carzinostaticus