Diagnostic structural criteria for the anomeric effect in carbohydrates and inferences of general significance on their scope and limitations

A systematic analysis of 529 carbohydrate structures that contain OCO units, retrieved from the Cambridge Structural Database, was performed with regard to the bond lengths (CO) and bond (COC and OCO) angles as they depend on the dihedral angles in the sequence COCOC. This dependence was...

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Bibliographic Details
Published in:Carbohydrate research 1990-09, Vol.206 (1), p.21-39
Main Authors: Schleifer, Leah, Senderowitz, Hanoch, Aped, Pinchas, Tartakovsky, Evgeny, Fuchs, Benzion
Format: Article
Language:English
Subjects:
Atomic and molecular physics
Electronic structure of atoms, molecules and their ions: theory
Exact sciences and technology
Physics
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Summary:A systematic analysis of 529 carbohydrate structures that contain OCO units, retrieved from the Cambridge Structural Database, was performed with regard to the bond lengths (CO) and bond (COC and OCO) angles as they depend on the dihedral angles in the sequence COCOC. This dependence was then interpreted in terms of the anomeric effect. Known and new concepts that concern the manifestations of the anomeric and exo-anomeric effects were thus reassessed. A set of structural criteria of diagnostic value was defined which, together with qualifying arguments, allow evaluation of the scope and limitations of these stereoelectronic effects in carbohydrate systems.
ISSN:0008-6215
1873-426X
DOI:10.1016/0008-6215(90)84003-D