A novel approach to the 1-deoxynojirimycin system: synthesis from sucrose of 2-acetamido-1, 2-dideoxynojirimycin, as well as some 2-N-modified derivatives.
6-Azido-1,3,4-tri-O-benzyl-6-deoxy-D-fructofuranose can be easily obtained in two steps from the known 6,6'-diazido-6,6'-dideoxysucrose (available in two steps from sucrose) and cyclized by controlled hydrogenation and concomitant intramolecular reductive amination to give 3,4,6-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol, a partially protected derivative of 1-deoxymannojirimycin. After N-protection, position 2 is regio-specifically available to modification. This novel approach was taken advantage of in a synthesis of 2-acetamido-1,2- dideoxynojirimycin and new analogues thereof. Results of inhibition studies conducted with these new compounds employing N-acetylhexosaminidases of various sources are discussed.
Gradnig
G
G
Institut für Organische Chemie der Technischen Universität Graz, Austria.
Legler
G
G
Stütz
A E
AE
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D002417:Cattle; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D007887:Fabaceae / Q000201:enzymology; D006596:Hexosaminidases / Q000037:antagonists & inhibitors / Q000378:metabolism; D007668:Kidney / Q000201:enzymology; D015394:Molecular Structure; D010946:Plants, Medicinal; D012908:Snails / Q000201:enzymology; D013395:Sucrose / Q000378:metabolism*
D004791:Enzyme Inhibitors; C053655:2-acetamido-1,5-imino-1,2,5-trideoxy-D-glucitol; D017485:1-Deoxynojirimycin; D013395:Sucrose; D006596:Hexosaminidases