Generalized anomeric effect in gem-diamines: stereoselective synthesis of alpha-N-linked disaccharide mimics.
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.
Sánchez-Fernández
Elena M
EM
Instituto de Investigaciones Químicas, CSIC and Universidad de Sevilla, Isla de la Cartuja, E-41092 Sevilla, Spain.
Rísquez-Cuadro
Rocío
R
Aguilar-Moncayo
Matilde
M
García-Moreno
M Isabel
MI
Ortiz Mellet
Carmen
C
García Fernández
José M
JM
D003959:Diamines / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007534:Isomaltose / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008320:Maltose / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018716:Molecular Mimicry; D009834:Oligo-1,6-Glucosidase / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism
D003959:Diamines; D004791:Enzyme Inhibitors; D007534:Isomaltose; D008320:Maltose; C075822:glucopyranosylamine; D009834:Oligo-1,6-Glucosidase; D005944:Glucosamine