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Characterization of the epoxide hydrolase NcsF2 from the neocarzinostatin biosynthetic gene cluster.

ABSTRACT: 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.

SUBMITTER: Lin S

PROVIDER: S-EPMC2929678 | biostudies-literature | 2010 Sep

REPOSITORIES: biostudies-literature

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Characterization of the epoxide hydrolase NcsF2 from the neocarzinostatin biosynthetic gene cluster.

Lin Shuangjun S Horsman Geoffrey P GP Shen Ben B

Organic letters 20100901 17

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 a ...[more]

PMID: 20704329

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