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Issue 4, 2012
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Conformational analysis of seven-membered 1-N-iminosugars by NMR and molecular modelling

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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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Publication details

The article was received on 18 Nov 2011, accepted on 05 Jan 2012 and first published on 09 Feb 2012


Article type: Paper
DOI: 10.1039/C2NJ20967E
Citation: 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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