Enantioselective, ketoreductase-based entry into pharmaceutical building blocks: ethanol as tunable nicotinamide reductant.

Organic Letters
Sylvain BroussyDavid B Berkowitz

Abstract

The use of NADH- and NADPH-dependent ketoreductases to access enantioenriched pharmaceutical building blocks is reported. Seven structurally diverse synthons are obtained, including those for atomoxetine (KRED 132), talampanel (RS1-ADH and CPADH), Dolastatin (KRED 132), and fluoxetine (KRED 108/132). Ethanol may be used as stoichiometric reductant, regenerating both nicotinamide cofactors, particularly under four-electron redox conditions. Its favorable thermodynamic and economic profile, coupled with its advantageous dual cosolvent role, suggests a new application for biomass-derived ethanol.

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Citations

Apr 30, 2011·Chemical Reviews·Eduardo García-UrdialesVicente Gotor
Nov 6, 2015·Journal of the American Chemical Society·Qi-Kai KangYong Tang
Sep 17, 2013·Chemistry & Biology·Pouya JavidpourShiou-Chuan Tsai
Aug 22, 2016·Bioorganic Chemistry·Anju ChadhaSantosh Kumar Padhi
Jan 12, 2017·Applied Microbiology and Biotechnology·Yu-Guo ZhengZhi-Qiang Liu
Dec 2, 2015·Advanced Synthesis & Catalysis·Gregory A Applegate, David B Berkowitz
Apr 16, 2021·The Journal of Organic Chemistry·Virendra K TiwariDavid B Berkowitz
May 10, 2017·Chemical Reviews·Joerg H SchrittwieserWolfgang Kroutil
Jun 17, 2014·The Journal of Organic Chemistry·Mengmeng ZhaoZhaoguo Zhang
Apr 21, 2012·The Journal of Organic Chemistry·Eduardo BustoVicente Gotor

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