Synthesis of (+)- and (-)-nojirimycin and their 1-deoxy derivatives from myo-inositol.
The conversion of the naturally abundant cyclitol, myo-inositol (4), into (+)-nojirimycin (1a), its enantiomer (1b), and their 1-deoxy analogues (2a and 2b) is described. Biological assay of 2a, 2b, and the bisulfite adducts of 1a and 1b (3a and 3b) showed that the compounds having the unnatural L-gluco configuration (2b and 3b) possess moderate-to-high inhibitory activity against almond beta-D-glucosidase and bovine liver beta-D-galactosidase.
Chida
N
N
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan.
Furuno
Y
Y
Ikemoto
H
H
Ogawa
S
S
D017485:1-Deoxynojirimycin / Q000138:chemical synthesis* / Q000494:pharmacology / Q000031:analogs & derivatives; D000900:Anti-Bacterial Agents / Q000737:chemistry*; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D007294:Inositol / Q000737:chemistry*; D013237:Stereoisomerism; D013393:Sucrase / Q000037:antagonists & inhibitors; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors; D001617:beta-Glucosidase / Q000037:antagonists & inhibitors
D000900:Anti-Bacterial Agents; D017485:1-Deoxynojirimycin; D007294:Inositol; D006026:Glycoside Hydrolases; D001617:beta-Glucosidase; D001616:beta-Galactosidase; D013393:Sucrase; D005944:Glucosamine; C013626:nojirimycin