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

Leah Schleifer, Hanoch Senderowitz, Pinchas Aped, Evgeny Tartakovsky, Benzion Fuchs

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

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

Original languageEnglish
Pages (from-to)21-39
Number of pages19
JournalCarbohydrate Research
Volume206
Issue number1
DOIs
StatePublished - 30 Sep 1990
Externally publishedYes

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