1-Aza-sugars from D-glucose. Preparation of 1-deoxy-5-dehydroxymethyl-nojirimycin, its analogues and evaluation of glycosidase inhibitory activity.
D-glucose derived pentodialdoses 11a-c on reduction followed by tosylation, azide displacement, hydrogenation and protection with -Cbz group gave N-Cbz protected compounds 14a-c, respectively, which on removal of 1,2-acetonide functionality and hydrogenation afforded corresponding 1-aza-sugars 3, 9 and 10 in good overall yields. The glycosidase inhibition activity of these 1-aza-sugars was tested with sweet almond as a rich source of different glycosidases.
Patil
Nitin T
NT
Department of Chemistry, Garware Research Centre, University of Pune, Pune-411 007, India.
John
Sheeja
S
Sabharwal
Sushma G
SG
Dhavale
Dilip D
DD
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives; D001372:Aza Compounds / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005944:Glucosamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005947:Glucose / Q000737:chemistry*; D005959:Glucosidases / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared
C465519:1-deoxy-5-dehydroxymethyl-nojirimycin; D001372:Aza Compounds; D004791:Enzyme Inhibitors; D017485:1-Deoxynojirimycin; D005959:Glucosidases; D005947:Glucose; D005944:Glucosamine