Design and synthesis of glycosidase inhibitor 5-amino-1,2,3,4-cyclohexanetetrol derivatives from (-)-vibo-quercitol.
In continuation of development of bioactive inositol derivatives, a 1-O-methyl derivative of 5-amino-5-deoxy-L-talo-quercitol was designed and synthesized as an analogue of the strong alpha-fucosidase inhibitor, 5a-carba-alpha-L-fucopyranosylamine, the methyl branch being replaced with methoxyl, and demonstrated to be a moderate alpha-fucosidase inhibitor. The present approach provides a possible route to apply alkyl ethers of aminodeoxyinositols as hexopyranose mimics of biological interest.
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
Asada
Miwako
M
Ooki
Yoriko
Y
Mori
Midori
M
Itoh
Masayoshi
M
Korenaga
Takashi
T
D000818:Animals; D002417:Cattle; D003069:Coffee / Q000201:enzymology; D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015195:Drug Design; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D007668:Kidney / Q000201:enzymology; D008099:Liver / Q000201:enzymology; D015394:Molecular Structure; D027861:Prunus / Q000201:enzymology; D013329:Structure-Activity Relationship; D005644:alpha-L-Fucosidase / Q000037:antagonists & inhibitors*
D003069:Coffee; D003510:Cyclohexanes; D004791:Enzyme Inhibitors; D006026:Glycoside Hydrolases; D005644:alpha-L-Fucosidase