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A C‐linked Glycomimetic in the Gas Phase and in Solution: Synthesis and Conformation of the Disaccharide Manα(1,6)‐C‐ManαOPh |
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| Authors: | Ludovic Drouin Dr E?Cristina Stanca‐Kaposta Dr Priptal Saundh Antony?J Fairbanks Dr Sebastian Kemper Timothy?D?W Claridge Dr John?P Simons Prof |
| Institution: | 1. Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA (UK), Fax: (+44)?1865‐285002;2. Department of Chemistry, Physical and Theoretical Chemistry Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QZ (UK);3. present address: Institut für Experimentalphysik, Freie Universitaet Berlin, Arnimallee 14, 14195, Berlin (Germany), Fax: (+49)?30‐838‐55567 |
| Abstract: | The effect of carbon is subtle but sweet : The flexible C‐linkage in the newly synthesised C‐glycosyl mimetic, Manα(1,6)‐C‐ManαOPh allows OH? π bonding, both in the gas phase and in aqueous solution. This interaction is absent in the O‐linked disaccharide (see figure).  |
| Keywords: | ab initio calculations carbohydrates conformational analysis NMR spectroscopy sigmatropic rearrangement |