Literature DB >> 29932340

Baeyer-Villiger Monooxygenase-Mediated Synthesis of Esomeprazole As an Alternative for Kagan Sulfoxidation.

Yong Koy Bong1, Shiwei Song1, Jovana Nazor1,2, Michael Vogel1, Magnus Widegren1, Derek Smith1, Steven J Collier2, Rob Wilson1,2, S M Palanivel1, Karthik Narayanaswamy1, Ben Mijts2, Michael D Clay2, Ryan Fong2, Jeff Colbeck2, Amritha Appaswami2, Sheela Muley2, Jun Zhu2, Xiyun Zhang2, Jack Liang2, David Entwistle1,2.   

Abstract

A wild-type Baeyer-Villiger monooxygenase was engineered to overcome numerous liabilities in order to mediate a commercial oxidation of pyrmetazole to esomeprazole, using air as the terminal oxidant in an almost exclusively aqueous reaction matrix. The developed enzyme and process compares favorably to the incumbent Kagan inspired chemocatalytic oxidation, as esomeprazole was isolated in 87% yield, in >99% purity, with an enantiomeric excess of >99%.

Entities:  

Year:  2018        PMID: 29932340     DOI: 10.1021/acs.joc.8b00468

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  6 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

2.  Immobilization of Baeyer-Villiger monooxygenase from acetone grown Fusarium sp.

Authors:  Michio Takagi; Kotchakorn T Sriwong; Ayaka Masuda; Nozomi Kawaguchi; Shusuke Fukui; Lan Huong Le Viet; Dai-Ichiro Kato; Takashi Kitayama; Mikio Fujii; Afifa Ayu Koesoema; Tomoko Matsuda
Journal:  Biotechnol Lett       Date:  2022-01-27       Impact factor: 2.461

3.  Engineering Isopropanol Dehydrogenase for Efficient Regeneration of Nicotinamide Cofactors.

Authors:  Qiao Jia; Yu-Cong Zheng; Hai-Peng Li; Xiao-Long Qian; Zhi-Jun Zhang; Jian-He Xu
Journal:  Appl Environ Microbiol       Date:  2022-04-20       Impact factor: 5.005

Review 4.  Properties and Mechanisms of Flavin-Dependent Monooxygenases and Their Applications in Natural Product Synthesis.

Authors:  Yaming Deng; Quan Zhou; Yuzhou Wu; Xi Chen; Fangrui Zhong
Journal:  Int J Mol Sci       Date:  2022-02-27       Impact factor: 5.923

5.  Mutations Increasing Cofactor Affinity, Improve Stability and Activity of a Baeyer-Villiger Monooxygenase.

Authors:  Hamid R Mansouri; Oriol Gracia Carmona; Julia Jodlbauer; Lorenz Schweiger; Michael J Fink; Erik Breslmayr; Christophe Laurent; Saima Feroz; Leticia C P Goncalves; Daniela V Rial; Marko D Mihovilovic; Andreas S Bommarius; Roland Ludwig; Chris Oostenbrink; Florian Rudroff
Journal:  ACS Catal       Date:  2022-09-13       Impact factor: 13.700

Review 6.  Is it time for biocatalysis in fragment-based drug discovery?

Authors:  Jeremy I Ramsden; Sebastian C Cosgrove; Nicholas J Turner
Journal:  Chem Sci       Date:  2020-10-07       Impact factor: 9.825

  6 in total

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