Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/37657
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Title: 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
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
URI: http://hdl.handle.net/10261/37657
ISSN: 1523-7060
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Citation: Organic Letters 11(15): 3306-3309 (2009)
References: 19606851
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