Synthesis of isotopically labeled D-[1'-13C]ribonucleoside phosphoramidites.
The preparation of fully protected labeled diisopropylamino-beta-cyanoethyl-[1'-13C]ribonucleoside phosphoramidites with regioisomeric purity is described. We demonstrated in this paper that a regioselective 2'-O-silylation, through a 3',5'-O-di-tert-butylsilanediyl protection, has been applied for the synthesis of [1'-13C]ribonucleoside phosphoramidite units. This method allowed us to obtain only the desired 2'-O-silyl-3'-O-phosphoramidites avoiding the undesired 3'-O-silyl-2'-O-phosphoramidite nucleosides isolated by standard procedures. This is a suitable procedure to RNA precursors with respect to the isotope-containing precursors.
Saito
Y
Y
Institut de Chimie Organique et Analytique, CNRS UMR 6005, Université d'Orléans, France.
Nyilas
A
A
Agrofoglio
L A
LA
D002247:Carbon Isotopes; D007202:Indicators and Reagents; D007553:Isotope Labeling / Q000379:methods; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009843:Oligoribonucleotides / Q000138:chemical synthesis; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012313:RNA / Q000138:chemical synthesis; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry
D002247:Carbon Isotopes; D007202:Indicators and Reagents; D009843:Oligoribonucleotides; D009943:Organophosphorus Compounds; D012263:Ribonucleosides; D012313:RNA