Characterization of the Epoxide Hydrolase NcsF2 from the Neocarzinostatin Biosynthetic Gene Cluster

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• 作者：Shuangjun Lin ; Geoffrey P. Horsman ; Ben Shen
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：September 3, 2010
• 年：2010
• 卷：12
• 期：17
• 页码：3816-3819
• 全文大小：227K
• 年卷期：v.12,no.17(September 3, 2010)
• ISSN：1523-7052

文摘

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 H₂O 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.