Skip to Content
Merck
  • Characterization of the epoxide hydrolase NcsF2 from the neocarzinostatin biosynthetic gene cluster.

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

Organic letters (2010-08-14)
Shuangjun Lin, Geoffrey P Horsman, Ben Shen
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(R)-(+)-Styrene oxide, 97%, optical purity ee: 97% (GLC)
Sigma-Aldrich
Styrene oxide, 97%
Sigma-Aldrich
(S)-(−)-Styrene oxide, 98%, optical purity ee: 98% (GC)