Literature DB >> 25073518

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

Toru Matsui1, Yasumasa Dekishima, Makoto Ueda.   

Abstract

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.

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Year:  2014        PMID: 25073518     DOI: 10.1007/s00253-014-5932-z

Source DB:  PubMed          Journal:  Appl Microbiol Biotechnol        ISSN: 0175-7598            Impact factor:   4.813


  5 in total

1.  A Baeyer-Villiger monooxygenase from Cupriavidus basilensis catalyzes asymmetric synthesis of (R)-lansoprazole and other pharmaco-sulfoxides.

Authors:  Feng Liu; Chao Shou; Qiang Geng; Chen Zhao; Jianhe Xu; Huilei Yu
Journal:  Appl Microbiol Biotechnol       Date:  2021-03-29       Impact factor: 4.813

Review 2.  Reviewing a plethora of oxidative-type reactions catalyzed by whole cells of Streptomyces species.

Authors:  Sara Salama; Mohamed H Habib; Rajni Hatti-Kaul; Yasser Gaber
Journal:  RSC Adv       Date:  2022-03-01       Impact factor: 3.361

3.  Enantioselective sulfoxidation using Streptomyces glaucescens GLA.0.

Authors:  Sara Salama; Tarek Dishisha; Mohamed H Habib; Ahmed Z Abdelazem; Walid Bakeer; Mahmoud Abdel-Latif; Yasser Gaber
Journal:  RSC Adv       Date:  2020-09-01       Impact factor: 4.036

4.  Enantioseparation, Stereochemical Assignment and Chiral Recognition Mechanism of Sulfoxide-Containing Drugs.

Authors:  Fei Xiong; Bei-Bei Yang; Jie Zhang; Li Li
Journal:  Molecules       Date:  2018-10-18       Impact factor: 4.411

Review 5.  Two-Component FAD-Dependent Monooxygenases: Current Knowledge and Biotechnological Opportunities.

Authors:  Thomas Heine; Willem J H van Berkel; George Gassner; Karl-Heinz van Pée; Dirk Tischler
Journal:  Biology (Basel)       Date:  2018-08-02
  5 in total

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