Lipase-catalyzed regioselective monoacetylation of unsymmetrical 1,5-primary diols

International audience Lipase B from Candida antarctica (CALB) has been selected as the most suitable enzyme to catalyze the regioselective monoacetylation of 1,5-diol isoprostane intermediate, using vinyl acetate as an acyl transfer reagent in THF.We next applied this reaction on linear 2-substitut...

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Bibliographic Details
Published in:The Journal of Organic Chemistry
Main Authors: Oger, Camille, Marton, Zsuzsanna, Brinkmann, Yasmin, Bultel-Poncé, Valérie, Durand, Thierry, Graber, Marianne, Galano, Jean-Marie
Other Authors: Institut des Biomolécules Max Mousseron Pôle Chimie Balard (IBMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie - CNRS Chimie (INC-CNRS)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), LIttoral ENvironnement et Sociétés (LIENSs), La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS)
Format: Article in Journal/Newspaper
Language:English
Published: HAL CCSD 2010
Subjects:
[SDV.BIO]Life Sciences [q-bio]/Biotechnology
[INFO.INFO-BT]Computer Science [cs]/Biotechnology
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Antarc*
Antarctica
Online Access:https://hal.science/hal-00647807
https://hal.science/hal-00647807/document
https://hal.science/hal-00647807/file/Manuscript_corrige_ressoumis_joc.pdf
https://doi.org/10.1021/jo902541c
Description
Summary:International audience Lipase B from Candida antarctica (CALB) has been selected as the most suitable enzyme to catalyze the regioselective monoacetylation of 1,5-diol isoprostane intermediate, using vinyl acetate as an acyl transfer reagent in THF.We next applied this reaction on linear 2-substituted, 2,20-disubstituted-1,5- pentanediols, and cyclic 2,3-disubstituted-1,5-pentanediols. To rationalize the regioselectivity observed, molecular docking simulations were performed.

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