Issue 21, 2008
From the journal:

Organic & Biomolecular Chemistry

N-Acyl glycinates as acyl donors in serine protease-catalyzed kinetic resolution of amines. Improvement of selectivity and reaction rate†

Malek Nechab,ab   Lahssen El Blidi,a   Nicolas Vanthuyne,b   Stéphane Gastaldi,*a   Michèle P. Bertrand*a  and  Gérard Gil*b  

* Corresponding authors

a Laboratoire de Chimie Moléculaire Organique, LCP UMR 6264, Boite 562, Université Paul Cézanne, Aix-Marseille III, Faculté des Sciences St Jérôme, Avenue Escadrille Normandie-Niemen, Marseille Cedex 20, France
E-mail: michele.bertrand@univ-cezanne.fr

b Laboratoire de Stéréochimie Dynamique et Chiralité, ISM2, UMR 6263, Université Paul Cézanne, Aix-Marseille III, Faculté des Sciences St Jérôme, Avenue Escadrille Normandie-Niemen, Marseille Cedex 20, France
E-mail: gerard.gil@univ-cezanne.fr

Abstract

Enzymatic kinetic resolution of aliphatic and benzylic amines leading to (S)-amides was achieved by using alkaline protease as the catalyst and N-octanoyl glycine trifluoroethyl ester as the acyl donor; enantioselectivity ranged between 4 to 244, while reaction times were dramatically shortened and ranged between 15 min to 6 h.

Graphical abstract: N-Acyl glycinates as acyl donors in serine protease-catalyzed kinetic resolution of amines. Improvement of selectivity and reaction rate

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Article information

DOI
https://doi.org/10.1039/B812089G
Article type
Paper
Submitted
15 Jul 2008
Accepted
18 Jul 2008
First published
02 Sep 2008

Org. Biomol. Chem., 2008,6, 3917-3920

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N-Acyl glycinates as acyl donors in serine protease-catalyzed kinetic resolution of amines. Improvement of selectivity and reaction rate

M. Nechab, L. El Blidi, N. Vanthuyne, S. Gastaldi, M. P. Bertrand and G. Gil, Org. Biomol. Chem., 2008, 6, 3917 DOI: 10.1039/B812089G

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