Synthesis and evaluation of glucocerebrosidase inhibitory activity of anhydro deoxyinositols from (+)-epi- and (-)-vibo-quercitols.
Twelve 1,2- and 2,3-anhydro-1,2,3,4,5-cyclohexanepentols were synthesized from (+)-epi- and (-)-vibo-quercitols, readily available by bioconversion of myo-inositol, and assayed for inhibitory activity against glucocerebrosidase (mouse liver). Among them 1L-1,2-anhydro-1,2,4/3,5-cyclohexanepentol, the 3-deoxy derivative of the irreversible inhibitor conduritol B epoxide (CBE), has been demonstrated to be a highly potent and specific inhibitor, almost comparable to the parent compound.
Ogawa
S
S
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan.
Uetsuki
S
S
Tezuka
Y
Y
Morikawa
T
T
Takahashi
A
A
Sato
K
K
D000818:Animals; D005962:Glucosylceramidase / Q000037:antagonists & inhibitors*; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D008099:Liver / Q000201:enzymology; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008956:Models, Chemical
D007294:Inositol; D005962:Glucosylceramidase