title: Versatile approach for the synthesis of novel seven-membered iminocyclitols via ring-closing metathesis dihydroxylation reaction.
abstract: 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.
authors.affiliation: Department of Chemistry, Tsing Hua University, Hsinchu 300, Taiwan. cclin@chem.sinica.edu.tw
authors.forename: Chang-Ching
authors.initials: CC
authors.lastname: Lin
authors.forename: Yi-Shin
authors.initials: YS
authors.lastname: Pan
authors.forename: Laxmikant N
authors.initials: LN
authors.lastname: Patkar
authors.forename: Hsiu-Mei
authors.initials: HM
authors.lastname: Lin
authors.forename: Der-Lii M
authors.initials: DL
authors.lastname: Tzou
authors.forename: Thangaiah
authors.initials: T
authors.lastname: Subramanian
authors.forename: Chun-Cheng
authors.initials: CC
authors.lastname: Lin
mesh_terms: 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
chemical_list: D004791:Enzyme Inhibitors; D007097:Imines; D006026:Glycoside Hydrolases