Syntheses of sugar-related trihydroxyazepanes from simple carbohydrates and their activities as reversible glycosidase inhibitors.
Five diastereomeric trideoxy-1,6-iminohexitols were synthesised, and their inhibitory activities were determined against selected glycosidases. For comparison, 1,4,5-trideoxy-1,5-imino-D-lyxo-hexitol, the 4-deoxy derivative of 1-deoxymannojirimicin, was prepared by enzymatic isomerisation of 6-azido-3,6-dideoxy-D-ribo-hexose into the corresponding 2-ulose and subsequent hydrogenation accompanied by intramolecular reductive amination.
Department of Organic Chemistry, Technical University of Denmark, Building 201, DK-2800 Lyngby, Denmark.
S M
SM
Andersen
C
C
Ekhart
I
I
Lundt
A E
AE
Stütz
D000818:Animals; D001381:Azepines / Q000138:chemical synthesis* / Q000494:pharmacology*; D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry*; D002417:Cattle; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D008968:Molecular Conformation; D013329:Structure-Activity Relationship
D001381:Azepines; D002241:Carbohydrates; D004791:Enzyme Inhibitors; D006026:Glycoside Hydrolases