title: Regioselective oxidation of unprotected 1,4 linked glucans.
abstract: Palladium-catalyzed alcohol oxidation allows the chemo- and regioselective modification of unprotected 1,4 linked glucans. This is demonstrated in the two-step bisfunctionalization of 1,4 linked glucans up to the 7-mer. Introduction of an anomeric azide is followed by a highly regioselective mono-oxidation of the terminal C3-OH functionality. The resulting orthogonal bis-functionalized oligosaccharides are a viable alternative to PEG-spacers as demonstrated in the conjugation of a cysteine mutant of 4-oxalocrotonate tautomerase with biotin.
authors.affiliation: Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG Groningen, The Netherlands. A.J.Minnaard@rug.nl m.d.witte@rug.nl.
authors.forename: Niek N H M
authors.initials: NN
authors.lastname: Eisink
authors.forename: Jonas
authors.initials: J
authors.lastname: Lohse
authors.forename: Martin D
authors.initials: MD
authors.lastname: Witte
authors.forename: Adriaan J
authors.initials: AJ
authors.lastname: Minnaard
mesh_terms: D000438:Alcohols / Q000737:chemistry; D002384:Catalysis; D005936:Glucans / Q000737:chemistry*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000438:Alcohols; D005936:Glucans; D010165:Palladium