title: C3 Epimerization of Glucose, via Regioselective Oxidation and Reduction.
abstract: Palladium-catalyzed oxidation can single out the secondary hydroxyl group at C3 in glucose, circumventing the more readily accessible hydroxyl at C6 and the more reactive anomeric hydroxyl. Oxidation followed by reduction results in either allose or allitol, each a rare sugar that is important in biotechnology. Also, N-acetylglucosamine is selectively oxidized at C3. These results demonstrate that glucose and N-acetylglucosamine, the most readily available chiral building blocks, can be versatile substrates in homogeneous catalysis.
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 7, 9747 AG Groningen, The Netherlands.
authors.forename: Varsha R
authors.initials: VR
authors.lastname: Jumde
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 7, 9747 AG Groningen, The Netherlands.
authors.forename: Niek N H M
authors.initials: NN
authors.lastname: Eisink
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 7, 9747 AG Groningen, The Netherlands.
authors.forename: Martin D
authors.initials: MD
authors.lastname: Witte
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen , Nijenborgh 7, 9747 AG Groningen, The Netherlands.
authors.forename: Adriaan J
authors.initials: AJ
authors.lastname: Minnaard
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002384:Catalysis; D002852:Chromatography, Ion Exchange; D005947:Glucose / Q000737:chemistry*; D010084:Oxidation-Reduction; D066244:Proton Magnetic Resonance Spectroscopy; D019998:Racemases and Epimerases / Q000737:chemistry*
chemical_list: D019998:Racemases and Epimerases; D005947:Glucose; D000117:Acetylglucosamine