Flexible Enantiodivergent Synthesis and Biological Activity of Mannostatin Analogues, New Cyclitol Glycosidase Inhibitors.
Mannostatin A (1) is a new cyclitol inhibitor of glycoprotein processing. 2-Epimannostatin A (12) and its enantiomer (13) as well as their positional isomers (14, 15) were designed for probing structure-activity relationships in this class of glycosidase inhibitors. The analogues have been synthesized from (S)-4-((tert-butyldimethylsilyl)oxy)-2-cyclopentenone by an enantiodivergent strategy in a totally stereospecific fashion. Compound 13 showed inhibition against almond beta-glucosidase and is shown to be a topographical analogue of beta-D-glucopyranoside.
Nishimura
Yoshio
Y
Institute of Microbial Chemistry, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan.
Umezawa
Yoji
Y
Adachi
Hayamitsu
H
Kondo
Shinichi
S
Takeuchi
Tomio
T