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Closed Access item Generalized Anomeric Effect in gem-Diamines: Stereoselective Synthesis of α-N-Linked Disaccharide Mimics

Authors:Sánchez-Fernández, Elena M.
Rísquez-Cuadro, Rocio
Aguilar Moncayo, Matilde
García Moreno, María Isabel
Ortiz-Mellet, Carmen
García-Fernández, José Manuel
Keywords:Diamines, Enzyme inhibitors, Glucosamine, Isomaltose, Maltose, Molecular mimcry, Stereoisomerism, Glycopyranosylamine, Disaccharide
Issue Date:16-Jul-2009
Publisher:American Chemical Society
Citation:Organic Letters 11(15): 3306-3309 (2009)
Abstract:The orbital (negative hyperconjugation) contribution to the generalized anomeric effect is highly increased in bicyclic gem-diamines with a pseudoamide-type endocyclic nitrogen atom, which has been exploited for the stereoselective synthesis of configurationally stable alpha-N-linked azadisaccharide heteroanalogues of the natural disaccharides maltose and isomaltose as aglycon-sensitive inhibitors of isomaltase.
Description:4 páginas, 2 figuras, 3 esquemas.
Publisher version (URL):http://dx.doi.org/10.1021/ol901125n
Appears in Collections:(IIQ) Artículos

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