Convenient synthesis and evaluation of enzyme inhibitory activity of several N-alkyl-, N-phenylalkyl, and cyclic isourea derivatives of 5a-carba-alpha-DL-fucopyranosylamine.
Convenient synthesis and chemical modification of the potent alpha-L-fucosidase inhibitor, 5a-carba-alpha-DL-fucopyranosylamine (1), are described. Among seven N-substituted and three cyclic isourea derivatives newly prepared, the N-octyl derivative was found to be the strongest inhibitor of alpha-L-fucosidase (bovine kidney) more potent (K(i)=0.016 microM) than deoxyfuconojirimycin (K(i)=0.031 microM) with p-nitrophenyl-alpha-L-fucopyranoside as the substrate.
Ogawa
Seiichiro
S
Department of Life Sciences and Informatics, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, Yokohama, Japan. ogawa@bio.keio.ac.jp
Mori
Makiko
M
Takeuchi
Goichi
G
Doi
Fuminao
F
Watanabe
Maiko
M
Sakata
Yuko
Y
D000818:Animals; D002417:Cattle; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D005643:Fucose / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D007202:Indicators and Reagents; D007668:Kidney / Q000187:drug effects; D008968:Molecular Conformation; D013329:Structure-Activity Relationship; D005644:alpha-L-Fucosidase / Q000037:antagonists & inhibitors
C461193:5a-carbafucopyranosylamine; D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D005643:Fucose; D006026:Glycoside Hydrolases; D005644:alpha-L-Fucosidase