title: Synthesis and α-Glucosidase II inhibitory activity of valienamine pseudodisaccharides relevant to N-glycan biosynthesis.
abstract: Valienol-derived allylic C-1 bromides have been used as carbaglycosyl donors for α-xylo configured valienamine pseudodisaccharide synthesis. We synthesised valienamine analogues of the Glc(α1→3)Glc and Glc(α1→3)Man disaccharides representing the linkages cleaved by α-Glucosidase II in N-glycan biosynthesis. These (N1→3)-linked pseudodisaccharides were found to have some α-Glucosidase II inhibitory activity, while two other (N1→6)-linked valienamine pseudodisaccharides failed to inhibit the enzyme.
authors.affiliation: Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden. ian.cumpstey@sjc.oxon.org
authors.forename: Ian
authors.initials: I
authors.lastname: Cumpstey
authors.forename: Clinton
authors.initials: C
authors.lastname: Ramstadius
authors.forename: K
authors.initials: K
authors.lastname: Eszter Borbas
authors.forename: Dominic S
authors.initials: DS
authors.lastname: Alonzi
authors.forename: Terry D
authors.initials: TD
authors.lastname: Butters
mesh_terms: D055162:Biocatalysis; D060326:Chemistry Techniques, Synthetic; D053138:Cyclohexenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D065089:Glycoside Hydrolase Inhibitors; D006595:Hexosamines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008968:Molecular Conformation; D011134:Polysaccharides / Q000096:biosynthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D000520:alpha-Glucosidases / Q000378:metabolism
chemical_list: D053138:Cyclohexenes; D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D006595:Hexosamines; D011134:Polysaccharides; C030791:valienamine; D000520:alpha-Glucosidases