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January 1, 2020

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

Codexis Authors:
Yong Koy Bong, Shiwei Song, Jovana Nazor, Michael Vogel, Magnus Widegren, Derek Smith, Steven J. Collier, Rob Wilson, S. M. Palanivel, Karthik Narayanaswamy, Ben Mijts, Michael D. Clay, Ryan Fong, Jeff Colbeck, Amritha Appaswami, Sheela Muley, Jun Zhu, Xiyun Zhang, Jack Liang, and David Entwistle

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%.

Full Article published in The Journal of Organic Chemistry

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