Synthesis, glycosidase activity and X-ray crystallography of 3-amino-sugars.
The cleavage of two sugar epoxides, methyl 2,3-anhydro-alpha-D-mannopyranoside and 2,3-anhydro-alpha-D-allopyranoside, with amines is presented as a method for preparing a library of 3-amino-sugars (methyl 3-amino-3-deoxy-alpha-D-altropyranosides and methyl 3-amino-3-deoxy-alpha-D-glucopyranosides) as potential glycosidase inhibitors. Several of the altropyranosides were micromolar inhibitors of bovine liver beta-galactosidase and almond beta-glucosidase. X-ray crystal structures were determined for one of the methyl 3-amino-3-deoxy-alpha-D-altropyranosides, 4t, and one of the methyl 3-amino-3-deoxy-alpha-D-glucopyranosides, 6d.
Maxwell
Vanessa L
VL
Department of Chemistry, The University of Leicester, Leicester, LE1 7RH, UK.
Evinson
Emma L
EL
Emmerson
Daniel P G
DP
Jenkins
Paul R
PR
D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D000818:Animals; D002417:Cattle; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000737:chemistry*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors / Q000378:metabolism*; D008099:Liver / Q000201:enzymology; D015394:Molecular Structure
D000606:Amino Sugars; D004852:Epoxy Compounds; D006026:Glycoside Hydrolases