Preparation of 3-amino-3-deoxy derivatives of trehalose and sucrose and their activities.
The 3-keto derivatives of trehalose and sucrose respectively were prepared by a one-step enzymatic route using D-glucoside 3-dehydrogenase from Flavobacterium saccharophilum. Reductive amination of 3-ketotrehalose with ammonium acetate and sodium cyanoborohydride gave three compounds, 3-amino-3-deoxy-alpha-D-allopyranosyl alpha-D-glucopyranoside, 3-amino-3-deoxy-alpha-D-glucopyranosyl alpha-D-glucopyranoside (3-trehalosamine) and 3-amino-3-deoxy-alpha-D-mannopyranosyl alpha-D-glucopyranoside. From the reductive amination of 3-ketosucrose, 3-amino-3-deoxy-alpha-D-allopyranosyl beta-D-fructofuranoside and 3-amino-3-deoxy-alpha-D-glucopyranosyl beta-D-fructofuranoside were obtained. The antibiotic and glycohydrolase inhibitory activities of these 3-amino-3-deoxy derivatives were determined.
Asano
N
N
School of Pharmacy, Hokuriku University, Kanazawa, Japan.
Katayama
K
K
Takeuchi
M
M
Furumoto
T
T
Kameda
Y
Y
Matsui
K
K
D000586:Amination; D000900:Anti-Bacterial Agents / Q000032:analysis / Q000138:chemical synthesis* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D002462:Cell Membrane / Q000201:enzymology; D004187:Disaccharides / Q000138:chemical synthesis*; D004926:Escherichia coli / Q000187:drug effects; D005417:Flavobacterium / Q000201:enzymology; D005948:Glucose Dehydrogenases / Q000378:metabolism; D065089:Glycoside Hydrolase Inhibitors; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D006865:Hydrogenation; D015394:Molecular Structure; D009161:Mycobacterium / Q000187:drug effects; D010084:Oxidation-Reduction; D013211:Staphylococcus aureus / Q000187:drug effects; D013395:Sucrose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D014198:Trehalase / Q000037:antagonists & inhibitors; D014199:Trehalose / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D043324:beta-Fructofuranosidase
D000900:Anti-Bacterial Agents; D004187:Disaccharides; D065089:Glycoside Hydrolase Inhibitors; C059956:3-ketosucrose; C059957:3-ketotrehalose; D013395:Sucrose; D014199:Trehalose; D005948:Glucose Dehydrogenases; C051543:glucoside 3-dehydrogenase; D006026:Glycoside Hydrolases; D043324:beta-Fructofuranosidase; D014198:Trehalase