Stereoselective inhibition of alpha-L-fucosidases by N-benzyl aminocyclopentitols.
[structure: see text] (1R,2R,3R,4R,5R)-4-Amino-5-methylcyclopentane-1,2,3 -tr iol 8, its 4S stereoisomer 9, and their acyclic analogues (R)- and (S)-2-aminobutanol 11 and 12 are selective but moderate inhibitors of alpha-L-fucosidases. N-Benzylation selectively enhances inhibition potency for aminocyclopentitol 8 (--> 1, K(i) = 6.8 x 10(-)(7) M) but decreases inhibition for its 4S-stereoisomer 9 (--> 2, K(i) = 1.1 x 10(-)(4) M) and for the aminobutanols 11 (--> 13, no inhibition) and 12 (--> 14, no inhibition).
Blaser
A
A
Department of Chemistry & Biochemistry, University of Bern, Switzerland.
Reymond
J L
JL
D000605:Amino Alcohols / Q000378:metabolism*; D000818:Animals; D001596:Benzylamines / Q000378:metabolism*; D004791:Enzyme Inhibitors; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D006027:Glycosides; D006801:Humans; D007700:Kinetics; D018716:Molecular Mimicry; D013237:Stereoisomerism; D005644:alpha-L-Fucosidase / Q000037:antagonists & inhibitors*
D000605:Amino Alcohols; D001596:Benzylamines; D004791:Enzyme Inhibitors; D006027:Glycosides; D006026:Glycoside Hydrolases; D005644:alpha-L-Fucosidase