1. Generalized anomeric effect in gem-diamines: stereoselective synthesis of alpha-N-linked disaccharide mimics.
- Author
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Sánchez-Fernández EM, Rísquez-Cuadro R, Aguilar-Moncayo M, García-Moreno MI, Ortiz Mellet C, and García Fernández JM
- Subjects
- Enzyme Inhibitors chemistry, Enzyme Inhibitors pharmacology, Glucosamine chemical synthesis, Glucosamine chemistry, Isomaltose chemistry, Isomaltose pharmacology, Maltose chemistry, Maltose pharmacology, Stereoisomerism, Diamines chemistry, Enzyme Inhibitors chemical synthesis, Glucosamine analogs & derivatives, Isomaltose chemical synthesis, Maltose chemical synthesis, Molecular Mimicry, Oligo-1,6-Glucosidase antagonists & inhibitors
- 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.
- Published
- 2009
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