Issue 23, 2015
From the journal:

Organic & Biomolecular Chemistry

Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamates†

Kajitha Suthagar,a   Matthew I. J. Polsona  and  Antony J. Fairbanks*ab  

* Corresponding authors

a Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand
E-mail: antony.fairbanks@canterbury.ac.nz
Fax: +64 3364 2110
Tel: +64 3364 3097

b Biomolecular Interaction Centre, University of Canterbury, Private Bag 4800, Christchurch 8140, New Zealand

Abstract

De-protected arabino N-glycosyl sulfamides, sulfonamides and sulfamates were found to mutarotate and convert from the furanose to the thermodynamically more stable pyranose form in aqueous solution. The presence of a strongly electron withdrawing group in the alkyl chain stopped mutarotation and furanose/pyranose equilibration, allowing the isolation of the first unprotected furanose N-glycosyl sulfonamide.

Graphical abstract: Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamates

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Article information

DOI
https://doi.org/10.1039/C5OB00851D
Article type
Paper
Submitted
28 Apr 2015
Accepted
12 May 2015
First published
12 May 2015

Org. Biomol. Chem., 2015,13, 6573-6579

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Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamates

K. Suthagar, M. I. J. Polson and A. J. Fairbanks, Org. Biomol. Chem., 2015, 13, 6573 DOI: 10.1039/C5OB00851D

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