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Conformational analysis of isopropylidene-protected C-glycosyl derivatives of 3-deoxy-d-manno-2-octulosonic acid (Kdo) in the solid state and in solution

✍ Scribed by Martin Orbe; Kristina Luthman; Tommy Wåglund; Alf Claesson; Ingeborg Csöregh

Publisher: Elsevier Science
Year: 1991
Tongue: English
Weight: 955 KB
Volume: 211
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(91)84141-z

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✦ Synopsis

The favoured conformations of a series of C-glycosyl derivatives of 4,5:7,8-di-O-isopropylidene-3deoxy-D-munno-2-octulosonic acid (Kdo) esters were analyzed by n.m.r. spectroscopy and in one instance by X-ray crystallography. The Kdo derivatives were found to adopt a skew-boat conformation (& + OS,) in solution which corresponds well to the solid-state conformation. The skew-boat conformation of the pyranose ring appeared to be imposed solely by the 4,5-dioxolane ring. Molecular-mechanics calculations [MM2(85)] on a model eompound identified two low-energy conformations of equal steric energy, namely a skew-boat conformation almost identical to the experimentally observed conformation, and a chair conformation ('C,).

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