title: Synthesis of sugar nucleotides by application of phosphoramidites.
abstract: A new method for the construction of pyrophosphates is reported based on the coupling of a sugar phosphate and a nucleoside phosphoramidite. The in situ formed phosphate-phosphite intermediate was subsequently oxidized with tBuOOH. Three UDP-N-acetylglucosamine derivatives were prepared using this one-pot procedure in good yields.
authors.affiliation: Leiden Institute of Chemistry, Bioorganic Chemistry, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA, Leiden, The Netherlands.
authors.forename: Henrik
authors.initials: H
authors.lastname: Gold
authors.forename: Pieter
authors.initials: P
authors.lastname: van Delft
authors.forename: Nico
authors.initials: N
authors.lastname: Meeuwenoord
authors.forename: Jeroen D C
authors.initials: JD
authors.lastname: Codée
authors.forename: Dmitri V
authors.initials: DV
authors.lastname: Filippov
authors.forename: Gerrit
authors.initials: G
authors.lastname: Eggink
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
authors.forename: Gijs A
authors.initials: GA
authors.lastname: van der Marel
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008956:Models, Chemical; D009705:Nucleosides / Q000737:chemistry; D009711:Nucleotides / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry; D017905:Phosphites / Q000737:chemistry; D014530:Uridine Diphosphate / Q000737:chemistry
chemical_list: D002241:Carbohydrates; D009705:Nucleosides; D009711:Nucleotides; D009943:Organophosphorus Compounds; D010710:Phosphates; D017905:Phosphites; C434331:phosphoramidite; D014530:Uridine Diphosphate; D000117:Acetylglucosamine