A disaccharide rearrangement catalyzed by molybdate anion in aqueous solution.
Reaction of a galactosylated 2-C-(hydroxymethyl)-tetrofuranose with paramolybdate ion-exchange resin in aqueous solution at 67 degrees C gave an equililibrium mixture containing the reactant aldofuranose (42%) and a 2-ketopentofuranose galactosylated at O1 (58%). Observation of this stereospecific rearrangement supports prior arguments that substituents at C2 of the branched-chain aldofuranose reactant are located in a sterically accessible pocket of the putative dimolybdate-saccharide reactive complex during epimerization. This rearrangement provides a new and convenient route to 2-ketosugars glycosylated at the exocyclic C1 position.
Wu
Qingquan
Q
Omicron Biochemicals, Inc., 115 South Hill Street, South Bend, Indiana 46617, USA.
Pan
Qingfeng
Q
Zhao
Shikai
S
Imker
Heidi
H
Serianni
Anthony S
AS
D000837:Anion Exchange Resins; D000838:Anions / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002384:Catalysis; D002852:Chromatography, Ion Exchange; D004187:Disaccharides / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D008982:Molybdenum / Q000737:chemistry*; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry*
D000837:Anion Exchange Resins; D000838:Anions; D004187:Disaccharides; D005663:Furans; D014867:Water; C044659:molybdate; D008982:Molybdenum