Work

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

Year: 2010

Type: article

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.

Source: Organic Letters

DOI: 10.1021/ol101473t

Authors: Shuangjun Lin, Geoffrey P. Horsman, Ben Shen

Institutions: University of Wisconsin System, University of Wisconsin–Madison

Language: English

Topic: Microbial Natural Products and Biosynthesis

Subfield: Pharmacology (medical)

Field: Medicine

Domain: Health Sciences

Open Access status: green

Funder: National Cancer Institute

Awards: UWCCC National Cooperative Drug Discovery Group for Can*, Enediyne Biosynthesis and Engineering, G2271657281, G3053038336