372176-98-2Relevant academic research and scientific papers
Total synthesis of 2′,3′,4′,5′,5′-2H5- ribonucleosides: The key building blocks for NMR structure elucidation of large RNA
Foeldesi,Trifonova,Dinya,Chattopadhyaya
, p. 6560 - 6570 (2007/10/03)
The diastereospecific chemical syntheses of uridine-2′,3′,4′,5′,5″-2H 5 (21a), adenosine-2′,3′,4′,5′,5″-2H 5 (21b), cytidine-2′,3′,4′,5′,5″-2H 52H5 (21c), and guanosine-2′,3′,4′,5′,5″-2H 5 (21d) (>97 atom % 2H at C2′, C3′, C4′, and C5′/C5″) have been achieved for their use in the solution NMR structure determination of oligo-RNA by the Uppsala "NMR-window" concept (refs 4a-c, 5a, 6), in which a small 1H segment is NMR-visible, while the rest is made NMR-invisible by incorporation of the deuterated blocks 21a-d. The deuterated ribonucleosides 21a-d have been prepared by the condensation of appropriately protected aglycone with 1-O-acetyl-2,3,5-tri-O-(4-toluoyl)-α/β-D-ribofuranose- 2,3,4,5,5′-2H5 (19), which has been obtained via diastereospecific deuterium incorporation at the C2 center of appropriate D-ribose-2H4 derivatives either through an oxidation-reduction-inversion sequence or a one-step deuterium-proton exchange in high overall yield (44% and 24%, respectively).
Synthetic studies to improve the deuterium labelling in nucleosides for facilitating structural studies of large RNAs by high-field NMR spectroscopy
Kundu,Trifonova,Dinya,Foeldesi,Chattopadhyaya
, p. 1333 - 1337 (2007/10/03)
Synthetic studies to prepare ribonucleosides deuterated at C2′ and the application of the developed procedures for the synthesis of 2H5-ribonucleosides from 1,2-O-isopropylidene-3-O-benzyl-ribofuranose-3,4,5,5′ -2H4/
