Issue 4, 2012
From the journal:

New Journal of Chemistry

Conformational analysis of seven-membered 1-N-iminosugars by NMR and molecular modelling†

Javier Pérez-Castells,a   Marco Fontanella,a   Ana Ardá,a   F. Javier Canãda,a   Matthieu Sollogoub,b   Yves Blériot‡*b  and  Jesús Jiménez-Barbero*a  

* Corresponding authors

a Centro de Investigaciones Biológicas, CSIC, 28040 Madrid, Spain
E-mail: jjbarbero@cib.csic.es
Fax: +34 915360432
Tel: +34 918373112

b UPMC Univ Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), FR 2769, C. 181, 4 place Jussieu, 75005 Paris, France

Abstract

The conformational analysis of a series of tri- and tetrahydroxyazepanes 1–6 designed as noeuromycin mimics has been carried out using 1H NMR spectroscopy assisted by molecular mechanics, molecular dynamics and Monte Carlo calculations. A marked flexibility for these compounds has been found. Superimposition of the branched azepanes with known glycosidase inhibitors (DMJ, DNJ, IFG and noeuromycin) was in accordance with the glycosidase inhibition profile of the polyhydroxylated azepanes. Additional STD experiments confirmed the potency and competitive character of azepane 3 towards almond β-glucosidase.

Graphical abstract: Conformational analysis of seven-membered 1-N-iminosugars by NMR and molecular modelling

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Article information

DOI
https://doi.org/10.1039/C2NJ20967E
Article type
Paper
Submitted
18 Nov 2011
Accepted
05 Jan 2012
First published
09 Feb 2012

New J. Chem., 2012,36, 1008-1013

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Conformational analysis of seven-membered 1-N-iminosugars by NMR and molecular modelling

J. Pérez-Castells, M. Fontanella, A. Ardá, F. J. Canãda, M. Sollogoub, Y. Blériot and J. Jiménez-Barbero, New J. Chem., 2012, 36, 1008 DOI: 10.1039/C2NJ20967E

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