title: Diastereoselective Synthesis of Glycosyl Phosphates by Using a Phosphorylase-Phosphatase Combination Catalyst.
abstract: Sugar phosphates play an important role in metabolism and signaling, but also as constituents of macromolecular structures. Selective phosphorylation of sugars is chemically difficult, particularly at the anomeric center. We report phosphatase-catalyzed diastereoselective "anomeric" phosphorylation of various aldose substrates with α-D-glucose 1-phosphate, derived from phosphorylase-catalyzed conversion of sucrose and inorganic phosphate, as the phosphoryl donor. Simultaneous and sequential two-step transformations by the phosphorylase-phosphatase combination catalyst yielded glycosyl phosphates of defined anomeric configuration in yields of up to 70 % based on the phosphate applied to the reaction. An efficient enzyme-assisted purification of the glycosyl phosphate products from reaction mixtures was established.
authors.affiliation: Institute of Biotechnology and Biochemical Engineering, Graz University of Technology, Petersgasse 12, 8010 Graz (Austria).
authors.forename: Patricia
authors.initials: P
authors.lastname: Wildberger
authors.affiliation: Institute of Biotechnology and Biochemical Engineering, Graz University of Technology, Petersgasse 12, 8010 Graz (Austria).
authors.forename: Martin
authors.initials: M
authors.lastname: Pfeiffer
authors.affiliation: Institute of Organic Chemistry, University of Vienna, Währingerstraße 38, 1090 Vienna (Austria).
authors.forename: Lothar
authors.initials: L
authors.lastname: Brecker
authors.affiliation: Institute of Biotechnology and Biochemical Engineering, Graz University of Technology, Petersgasse 12, 8010 Graz (Austria). bernd.nidetzky@tugraz.at.|acib - Austrian Centre of Industrial Biotechnology (Austria). bernd.nidetzky@tugraz.at.
authors.forename: Bernd
authors.initials: B
authors.lastname: Nidetzky
mesh_terms: D002384:Catalysis; D010744:Phosphoric Monoester Hydrolases / Q000737:chemistry*; D006005:Phosphorylases / Q000737:chemistry*; D013237:Stereoisomerism; D013403:Sugar Phosphates / Q000737:chemistry*
chemical_list: D013403:Sugar Phosphates; D006005:Phosphorylases; D010744:Phosphoric Monoester Hydrolases
keywords: biocatalysis; phosphatases; phosphorylases; phosphorylation; sugar phosphates