Versatile approach for the synthesis of novel seven-membered iminocyclitols via ring-closing metathesis dihydroxylation reaction.
Seven-membered iminocyclitols with diverse diastereomers were prepared starting with d- and l-serines and employing ring-closing olefin metathesis and dihydroxylation reaction sequence. The iminocyclitols were assayed for glycosidase inhibition and compound 20 was found to be a competitive inhibitor for beta-glucosidase with Ki 26.3 microM.
Lin
Chang-Ching
CC
Department of Chemistry, Tsing Hua University, Hsinchu 300, Taiwan. cclin@chem.sinica.edu.tw
Pan
Yi-Shin
YS
Patkar
Laxmikant N
LN
Lin
Hsiu-Mei
HM
Tzou
Der-Lii M
DL
Subramanian
Thangaiah
T
Lin
Chun-Cheng
CC
D018360:Crystallography, X-Ray; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors / Q000378:metabolism; D006900:Hydroxylation; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D004791:Enzyme Inhibitors; D007097:Imines; D006026:Glycoside Hydrolases