A short path synthesis of [13C/15N] multilabeled pyrimidine nucleosides starting from glucopyranose nucleosides.
The synthesis of fully [13C/15N] labeled pyrimidine nucleosides has been achieved from 13C-glucose and labeled nucleobases. The reaction scheme leads directly to the protected nucleosides without the need for the inversion of configuration of C-3 of 13C-glucose. This was achieved by an oxitative ring-opening reaction removing the carbon with the wrong configuration.
Lagoja
Irene M
IM
Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium.
Pochet
Sylvie
S
Boudou
Valerie
V
Little
Roy
R
Lescrinier
Eveline
E
Rozenski
Jef
J
Herdewijn
Piet
P
D002247:Carbon Isotopes; D002625:Chemistry, Organic / Q000379:methods; D002855:Chromatography, Thin Layer; D003500:Cyclization; D005947:Glucose / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D009587:Nitrogen Isotopes; D019906:Nuclear Magnetic Resonance, Biomolecular; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship; D014498:Uracil / Q000138:chemical synthesis
D002247:Carbon Isotopes; D007202:Indicators and Reagents; D009587:Nitrogen Isotopes; D011741:Pyrimidine Nucleosides; D014498:Uracil; D005947:Glucose