Synthesis and glycosidase inhibitory activity of some N-substituted 5a-carba-beta-fuco- and beta-galactopyranosylamines, and selected derivatives.
In the course of chemical modification of alpha-fucosidase inhibitors of 5a-carba-fucopyranosylamine type, an N-dodecyl derivative of the enantiomer 6-deoxy-5a-carba-beta-D-galactopyranosylamine demonstrated very strong inhibition of beta-galactosidase and beta-glucosidase. This finding led us to synthesize corresponding 6-hydroxy compounds, in order to elucidate structure-activity relationships for inhibitors of this type. Among four N-alkyl-5a-carba-beta-D-galactopyranosylamines prepared, the N-octyl derivative could be demonstrated to possess moderate activity toward alpha- and beta-galactosidases, and beta-glucosidase.
Ogawa
Seiichiro
S
Department of Biosciences and Informatics, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan. sogawa379@ybb.ne.jp
Fujieda
Shigeo
S
Sakata
Yuko
Y
Ishizaki
Masahiro
M
Hisamatsu
Seiichi
S
Okazaki
Kensuke
K
Ooki
Yoriko
Y
Mori
Midori
M
Itoh
Masayoshi
M
Korenaga
Takashi
T
D005688:Galactosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D020128:Inhibitory Concentration 50; D013329:Structure-Activity Relationship; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors; D001617:beta-Glucosidase / Q000037:antagonists & inhibitors
D005688:Galactosamine; D006026:Glycoside Hydrolases; D001617:beta-Glucosidase; D001616:beta-Galactosidase