title: Chemoenzymatic Synthesis of 4-Fluoro-N-Acetylhexosamine Uridine Diphosphate Donors: Chain Terminators in Glycosaminoglycan Synthesis.
abstract: Unnatural uridine diphosphate (UDP)-sugar donors, UDP-4-deoxy-4-fluoro-N-acetylglucosamine (4FGlcNAc) and UDP-4-deoxy-4-fluoro-N-acetylgalactosamine (4FGalNAc), were prepared using both chemical and chemoenzymatic syntheses relying on N-acetylglucosamine-1-phosphate uridylyltransferase (GlmU). The resulting unnatural UDP-sugar donors were then tested as substrates in glycosaminoglycan synthesis catalyzed by various synthases. UDP-4FGlcNAc was transferred onto an acceptor by Pastuerella multocida heparosan synthase 1 and subsequently served as a chain terminator.
authors.affiliation: Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute , Troy, New York 12180, United States.
authors.forename: Victor L
authors.initials: VL
authors.lastname: Schultz
authors.affiliation: Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute , Troy, New York 12180, United States.
authors.forename: Xing
authors.initials: X
authors.lastname: Zhang
authors.affiliation: Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute , Troy, New York 12180, United States.
authors.forename: Kathryn
authors.initials: K
authors.lastname: Linkens
authors.affiliation: Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute , Troy, New York 12180, United States.
authors.forename: Jenna
authors.initials: J
authors.lastname: Rimel
authors.affiliation: Department of Biochemistry and Molecular Biology, University of Oklahoma Health Sciences Center, Oklahoma Center for Medical Glycobiology , 940 Stanton L. Young Blvd., Oklahoma City, Oklahoma 73126, United States.
authors.forename: Dixy E
authors.initials: DE
authors.lastname: Green
authors.affiliation: Department of Biochemistry and Molecular Biology, University of Oklahoma Health Sciences Center, Oklahoma Center for Medical Glycobiology , 940 Stanton L. Young Blvd., Oklahoma City, Oklahoma 73126, United States.
authors.forename: Paul L
authors.initials: PL
authors.lastname: DeAngelis
authors.affiliation: Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute , Troy, New York 12180, United States.
authors.forename: Robert J
authors.identifier: 0000-0003-2219-5833
authors.initials: RJ
authors.lastname: Linhardt
mesh_terms: D055162:Biocatalysis; D002236:Carbohydrate Conformation; D006025:Glycosaminoglycans / Q000096:biosynthesis* / Q000737:chemistry; D009713:Nucleotidyltransferases / Q000737:chemistry / Q000378:metabolism*; D014539:Uridine Diphosphate Sugars / Q000096:biosynthesis / Q000737:chemistry
chemical_list: C000627293:4-fluoro-N-acetylhexosamine uridine diphosphate; D006025:Glycosaminoglycans; D014539:Uridine Diphosphate Sugars; D009713:Nucleotidyltransferases; C023226:UDPacetylglucosamine pyrophosphorylase