Issue 10, 2004
From the journal:

Organic & Biomolecular Chemistry

The first synthesis of substituted azepanes mimicking monosaccharides: a new class of potent glycosidase inhibitors

Hongqing Li,a   Yves Blériot,*a   Caroline Chantereau,a   Jean-Maurice Mallet,a   Matthieu Sollogoub,a   Yongmin Zhang,a   Eliazar Rodríguez-García,b   Pierre Vogel,b   Jesús Jiménez-Barberoc  and  Pierre Sinaÿ*a  

* Corresponding authors

a Ecole Normale Supérieure, Département de Chimie, UMR 8642, 24 rue Lhomond, 75231 Paris Cedex 05, France
E-mail: yves.bleriot@ens.fr, pierre.sinay@ens.fr

b Institut des Sciences et Ingéniérie Chimiques, Ecole Polytechnique Fédérale de Lausanne, BCH, CH-1015 Lausanne, Switzerland

c Centro de Investigaciones Biologicas, CSIC, Ramiro De Maeztu 9, 28040 Madrid, Spain

Abstract

The synthesis of the first examples of seven-membered ring iminoalditols, molecules displaying an extra hydroxymethyl substituent on their seven-membered ring compared to the previously reported polyhydroxylated azepanes, has been achieved from D-arabinose in 10 steps using RCM of a protected N-allyl-aminohexenitol as a key step. While the (2R,3R,4R)-2-hydroxymethyl-3,4-dihydroxy-azepane 10, a seven-membered ring analogue of fagomine, is a weak inhibitor of glycosidases, the (2R,3R,4R,5S,6S)-2-hydroxymethyl-3,4,5,6-tetrahydroxy-azepane 9 selectively inhibits green coffee bean α-galactosidase in the low micromolar range (Ki = 2.2 µM) despite a D-gluco relative configuration.

Graphical abstract: The first synthesis of substituted azepanes mimicking monosaccharides: a new class of potent glycosidase inhibitors

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Article information

DOI
https://doi.org/10.1039/B402542C
Article type
Paper
Submitted
20 Feb 2004
Accepted
19 Mar 2004
First published
20 Apr 2004

Org. Biomol. Chem., 2004,2, 1492-1499

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The first synthesis of substituted azepanes mimicking monosaccharides: a new class of potent glycosidase inhibitors

H. Li, Y. Blériot, C. Chantereau, J. Mallet, M. Sollogoub, Y. Zhang, E. Rodríguez-García, P. Vogel, J. Jiménez-Barbero and P. Sinaÿ, Org. Biomol. Chem., 2004, 2, 1492 DOI: 10.1039/B402542C

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