title: A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.
abstract: An overview of recent advances in glycosylation with particular emphasis on mechanism is presented. The mounting evidence for both the existence of glycosyl oxocarbenium ions as fleeting intermediates in some reactions, and the crucial role of the associated counterion in others is discussed. The extremes of the SN1 and SN2 manifolds for the glycosylation reaction are bridged by a continuum of mechanisms in which it appears likely that most examples are located.
authors.affiliation: Centre de Recherche de Gif, CNRS, Institut de Chimie des Substances Naturelles, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
authors.forename: Luis
authors.initials: L
authors.lastname: Bohé
authors.affiliation: Department of Chemistry, Wayne State University, 5101 Cass Ave, Detroit, MI 48202, USA. Electronic address: dcrich@chem.wayne.edu.
authors.forename: David
authors.initials: D
authors.lastname: Crich
mesh_terms: D002236:Carbohydrate Conformation; D006027:Glycosides / Q000737:chemistry; D006031:Glycosylation; D007700:Kinetics; D008958:Models, Molecular; D013057:Spectrum Analysis
chemical_list: D006027:Glycosides
keywords: Counter ions; Hydrogen bonding; Kinetics; Oxocarbenium ions
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