Biotechnological production of chiral organic sulfoxides: current state and perspectives.

Matsui, Toru; Dekishima, Yasumasa; Ueda, Makoto

Chiral organic sulfoxides (COSs) are important compounds that act as chiral auxiliaries in numerous asymmetric reactions and as intermediates in chiral drug synthesis. In addition to their optical resolution, stereoselective oxidation of sulfides can be used for COS production. This reaction is facilitated by oxygenases and peroxidases from various microbial resources. To meet the current demand for esomeprazole, a proton pump inhibitor used in the treatment of gastric-acid-related disorders, and the ( S)-isomer of an organic sulfoxide compound, omeprazole, a successful biotechnological production method using a Baeyer-Villiger monooxygenase (BVMO), was developed. In this review, we summarize the recent advancements in COS production using biocatalysts, including enzyme identification, protein engineering, and process development.

SULFOXIDES; SULFOXIDES synthesis; CHIRALITY; ASYMMETRIC synthesis; STEREOSELECTIVE reactions; OXYGENASES

Applied Microbiology & Biotechnology, 2014, Vol 98, Issue 18, p7699

0175-7598

Academic Journal

10.1007/s00253-014-5932-z