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Concerning the origin of the high beta-selectivity of glycosidation reactions of 2-deoxy-2-iodo-glucopyranosyl trichloroacetimidates. 2002

Pek Y Chong, and William R Roush
Department of Chemistry, University of Michigan, Ann Arbor 48109, USA.

[structure: see text] Studies on the glycosidation reactions of conformationally constrained glycosyl imidates 8a and 8b were performed to evaluate the possible involvement of "conformationally inverted" oxonium ion intermediates in glycosidation reactions with 2-deoxy-2-iodo-glucopyranosyl donors. The mechanistic implications of this study are discussed, and intermediates 23 and 24 are invoked to rationalize the observed beta-selectivities.

UI MeSH Term Description Entries
D002236 Carbohydrate Conformation The characteristic 3-dimensional shape of a carbohydrate. Carbohydrate Linkage,Carbohydrate Conformations,Carbohydrate Linkages,Conformation, Carbohydrate,Conformations, Carbohydrate,Linkage, Carbohydrate,Linkages, Carbohydrate
D006027 Glycosides Any compound that contains a constituent sugar, in which the hydroxyl group attached to the first carbon is substituted by an alcoholic, phenolic, or other group. They are named specifically for the sugar contained, such as glucoside (glucose), pentoside (pentose), fructoside (fructose), etc. Upon hydrolysis, a sugar and nonsugar component (aglycone) are formed. (From Dorland, 28th ed; From Miall's Dictionary of Chemistry, 5th ed) Glycoside
D006031 Glycosylation The synthetic chemistry reaction or enzymatic reaction of adding carbohydrate or glycosyl groups. GLYCOSYLTRANSFERASES carry out the enzymatic glycosylation reactions. The spontaneous, non-enzymatic attachment of reducing sugars to free amino groups in proteins, lipids, or nucleic acids is called GLYCATION (see MAILLARD REACTION). Protein Glycosylation,Glycosylation, Protein
D014238 Trichloroacetic Acid A strong acid used as a protein precipitant in clinical chemistry and also as a caustic for removing warts. Acide trichloracetique,Rubidium Trichloroacetate,Sodium Trichloroacetate,Acid, Trichloroacetic,Trichloroacetate, Rubidium,Trichloroacetate, Sodium,trichloracetique, Acide
D062845 Chloroacetates ACETIC ACID or acetic acid esters substituted with one or more CHLORINE atoms. Chloroacetic Acids,Acids, Chloroacetic

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