Organic Letters 2010-09-03

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

Shuangjun Lin, Geoffrey P Horsman, Ben Shen

Index: Org. Lett. 12(17) , 3816-9, (2010)

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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.