De novo asymmetric synthesis and biological evaluation of the trisaccharide portion of PI-080 and vineomycin B2.
A highly enantio- and diastereoselective synthesis of an alpha-L-aculose, alpha-L-rhodinose, and beta-D-olivose trisaccharide is described. The key transformations include the palladium-catalyzed glycosylation, Myers' reductive rearrangement, diastereoselective dihydroxylation, and regioselective Mitsunobu inversion. Significant apoptotic antitumor activity was found for this trisaccharide, which has implication for vineomycin B2 and PI-080 structure-activity relationship.
Yu
Xiaomei
X
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
O'Doherty
George A
GA
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003837:Deoxy Sugars / Q000737:chemistry; D006801:Humans; D015394:Molecular Structure; D013237:Stereoisomerism; D014312:Trisaccharides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
D000880:Anthraquinones; D003837:Deoxy Sugars; C533297:PI-080; D014312:Trisaccharides; C407877:olivose; C024277:vineomycin B2