Enantioselective, ketoreductase-based entry into pharmaceutical building blocks: ethanol as tunable nicotinamide reductant
Organic letters, 2009•ACS Publications
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 …
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 …
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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