title: Synthesis and evaluation of diastereoisomeric alkylating pseudo-disaccharides as potential affinity reagents for trehalase.
abstract: Reaction of (+/-)-(3/4,5,6)-4-bromo-5,6-epoxy-3-hydroxycyclohexene with 2,3,4,6-tetra-O-acetyl-1-thio-alpha-D-glucopyranose, followed by treatment of the resulting isolated diastereoisomeric 4-bromo-3,5-dihydroxycyclohexene 1-thioglycoside derivatives with base under phase-transfer conditions, gave (R)- and (S)-(3,4,6/5)-3,4-epoxy-6-S-(1-thio-alpha-D-glucopyranosyl)-5- hydroxycyclohexene. None of them was substrate or inhibitor for cockchafer trehalase.
authors.affiliation: Université de Caen, UFR des Sciences Pharmaceutiques, France.
authors.forename: E
authors.initials: E
authors.lastname: Bar-Guilloux
authors.forename: J
authors.initials: J
authors.lastname: Defaye
authors.forename: J
authors.initials: J
authors.lastname: Lehmann
authors.forename: R
authors.initials: R
authors.lastname: Nardin
authors.forename: D
authors.initials: D
authors.lastname: Robic
authors.forename: K
authors.initials: K
authors.lastname: Urbahns
mesh_terms: D000478:Alkylation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000737:chemistry*; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D013237:Stereoisomerism; D014198:Trehalase / Q000737:chemistry*
chemical_list: D004187:Disaccharides; D007202:Indicators and Reagents; D014198:Trehalase