Literature DB >> 19128188

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

Sylvain Broussy1, Ross W Cheloha, David 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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Year:  2009        PMID： 19128188      PMCID： PMC6027600          DOI： 10.1021/ol802464g

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  25 in total

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Review 10.  Advances in the enzymatic reduction of ketones.

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  8 in total

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5.  Structural and biochemical analyses of regio- and stereospecificities observed in a type II polyketide ketoreductase.

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6.  Combining a Clostridial enzyme exhibiting unusual active site plasticity with a remarkably facile sigmatropic rearrangement: rapid, stereocontrolled entry into densely functionalized fluorinated phosphonates for chemical biology.

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7.  Use of a robust dehydrogenase from an archael hyperthermophile in asymmetric catalysis-dynamic reductive kinetic resolution entry into (S)-profens.

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8.  The determinants of activity and specificity in actinorhodin type II polyketide ketoreductase.

Authors:  Pouya Javidpour; Joel Bruegger; Supawadee Srithahan; Tyler P Korman; Matthew P Crump; John Crosby; Michael D Burkart; Shiou-Chuan Tsai
Journal:  Chem Biol       Date:  2013-09-12
  8 in total

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