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A disaccharide rearrangement catalyzed by molybdate anion in aqueous solution
Qingquan Wu1, Qingfeng Pan, Shikai Zhao
1Omicron Biochemicals, Inc., 115 South Hill Street, South Bend, Indiana 46617, USA.
Abstract:
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.
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