Synthesis of sugar nucleotides by application of phosphoramidites.
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.
Gold
Henrik
H
Leiden Institute of Chemistry, Bioorganic Chemistry, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA, Leiden, The Netherlands.
van Delft
Pieter
P
Meeuwenoord
Nico
N
Codée
Jeroen D C
JD
Filippov
Dmitri V
DV
Eggink
Gerrit
G
Overkleeft
Herman S
HS
van der Marel
Gijs A
GA
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
D002241:Carbohydrates; D009705:Nucleosides; D009711:Nucleotides; D009943:Organophosphorus Compounds; D010710:Phosphates; D017905:Phosphites; C434331:phosphoramidite; D014530:Uridine Diphosphate; D000117:Acetylglucosamine