Chemoenzymatic synthesis of (2S)-2-arylpropanols through a dynamic kinetic resolution of 2-arylpropanals with alcohol dehydrogenases

Organic & Biomolecular Chemistry
Paola GallettiDaria Giacomini

Abstract

We applied Horse Liver Alcohol Dehydrogenase (HLADH) to the enantioselective synthesis of six (2S)-2-arylpropanols, useful intermediates in the synthesis of Profens. The influence of substrate structure and reaction conditions on yields and enantioselectivity were investigated. The high yields and high enantioselectivity towards the (S)-enantiomer obtained in the bioreduction of 2-arylpropionic aldehydes, clearly indicate the achievement of a DKR process through a combination of an enzyme-catalyzed kinetic reduction with a chemical base-catalyzed racemization of the unreacted aldehydes. The racemization step is represented by the keto-enol equilibrium of the aldehyde and can be controlled by modulating pH and reaction conditions.

References

Apr 1, 1990·European Journal of Drug Metabolism and Pharmacokinetics·D B Campbell
Oct 1, 1986·Biochemical Pharmacology·K WilliamsA Duffield
Nov 27, 1995·Biochemical Pharmacology·C ReichelS Menzel
Sep 24, 1999·Biochemistry·L A LeBrun, B V Plapp
Feb 17, 2000·International Journal of Pharmaceutics·X YuchunC Jiayong
Aug 14, 2003·Chemical Reviews·Oscar Pàmies, Jan-E Bäckvall
Apr 6, 2004·Current Opinion in Chemical Biology·Nicholas J Turner
Oct 30, 2004·Chirality·Ashraf Ghanem, Hassan Y Aboul-Enein
May 10, 2005·Biotechnology and Applied Biochemistry·Gang-Liang HuangPeng-George Wang
Jun 17, 2005·Chemical Communications : Chem Comm·Jai Jun Kim, Howard Alper
Dec 6, 2005·Organic & Biomolecular Chemistry·Gianfranco CainelliFrancesca Paradisi
Apr 26, 2007·Chemical Communications : Chem Comm·Xiaoguang Li, Benjamin List
Oct 27, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Guido SelloPatrizia Di Gennaro

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Citations

May 1, 2012·Molecular Biotechnology·Daniela QuagliaFrancesca Paradisi
Jan 12, 2017·Applied Microbiology and Biotechnology·Yu-Guo ZhengZhi-Qiang Liu
Apr 14, 2017·Angewandte Chemie·Moritz HönigErick M Carreira
Sep 1, 2012·Angewandte Chemie·Paul KönstFrank Hollmann
Nov 11, 2010·Chembiochem : a European Journal of Chemical Biology·Martyn E HulleyNigel S Scrutton
Dec 5, 2013·Organic & Biomolecular Chemistry·Cristina RodríguezVicente Gotor
Feb 27, 2018·Physical Chemistry Chemical Physics : PCCP·Karin JuliusRoland Winter
Sep 26, 2013·Chemical Society Reviews·Michał RachwalskiFloris P J T Rutjes
Dec 2, 2015·Advanced Synthesis & Catalysis·Gregory A Applegate, David B Berkowitz
Apr 15, 2018·Molecular Biotechnology·Jennifer Cassidy, Francesca Paradisi
Apr 25, 2020·Angewandte Chemie·Frank HollmannCaroline E Paul
Jul 16, 2013·Organic Letters·Juan Mangas-SánchezVicente Gotor-Fernández
Oct 13, 2021·BMC Biotechnology·Christian RappRegina Kratzer

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