335595-64-7Relevant academic research and scientific papers
Efficient synthesis of D-[1′-13c]-ribonucleosides for incorporation into oligo-RNA
Saito,Nyilas,Agrofoglio
, p. 937 - 940 (2007/10/03)
Syntheses of the monomer building blocks used for the solid-phase synthesis of specifically 1′-13C-labeled oligoribonucleotides from the D-[1-13C]ribose is presented. Procedure has been used for the selective formation of 2′-O-silylated ribonucleosides. After 5′-O-dimethoxytritylation, the synthesis of D-[1′-13C] ribonucleoside phosphoramidites has been achieved.
Synthesis of isotopically labeled D-[1′-13C]ribonucleoside phosphoramidites
Saito, Yoshio,Nyilas, Agnes,Agrofoglio, Luigi A.
, p. 83 - 90 (2007/10/03)
The preparation of fully protected labeled diisopropylamino-β-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.
13C-enriched ribonucleosides: Synthesis and application of 13C-1H and 13C-13C spin-coupling constants to assess furanose and N-glycoside bond conformations
Kline, Paul C.,Serianni, Anthony S.
, p. 7373 - 7381 (2007/10/02)
Adenosine (1), cytidine (2), guanosine (3), and uridine (4) have been prepared chemically with 13C enrichment (99 atom %) at C1′ and C2′ of the ribose ring. Reliable synthetic protocols have been developed to permit access to millimole quantities of labeled ribonucleosides required for structural studies of stable isotopically labeled oligonucleotides and for in vivo metabolism studies. High-resolution 1H and 13C NMR spectra of the enriched ribonucleosides have been obtained, and 13C-13C and 13C-1H spin-coupling constants have been measured for pathways within the β-D-ribofuranose ring and across the N-glycoside bond. Related couplings were determined in methyl α- and β-D-ribofuranosides (5, 6), and in two conformationally constrained nucleosides, 2,2′-anhydro-(1-β-D-arabinofuranosyl)uracil (7) and 2′,3′-O-isopropylidene-2,5′-O-cyclouridine (8). The latter data were used to construct a crude Karplus curve for the 13C-C-N-13C coupling pathway across the N-glycoside bond in 1-4. 1H-1H, 13C-1H, and 13C-13C coupling data are used to evaluate current models describing the conformational dynamics of 1-4 in aqueous solution.
