Communication: Blocked Disaccharide Analogs Bearing an Oxyimino Interglycosidic Bridge
- 1 January 1991
- journal article
- other
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 10 (4) , 723-728
- https://doi.org/10.1080/07328309108543945
Abstract
Oligosaccharide units in which a ONH group replaces the usual oxy bridge have been encountered in nature, for ex. in the antitumor antibiotic calicheamicin γ1,2 and the biological importance of this peculiar interglycosidic junction has been emphasized.3 The N-O bond is very different from the bonds habitually found in carbohydrate chemistry, owing, in particular, to its weakness and the presence of lone-pairs on its two hetero atoms. These characteristics considerably affect the conformational properties of molecules like calicheamicin. As we have developed,4 in the CHARMm force field,5 parameters pertaining to this bond, we needed models of disaccharides of this type to fit computed results in with experimental data. These O-N-disaccharide derivatives were easily obtained from the O-aminosugar derivative 1.6Keywords
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