Total synthesis of 2′,3′,4′,5′,5′-2H5- ribonucleosides: The key building blocks for NMR structure elucidation of large RNA

A. Földesi, A. Trifonova, Z. Dinya, J. Chattopadhyaya

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Abstract

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).

Original languageEnglish
Pages (from-to)6560-6570
Number of pages11
JournalJournal of Organic Chemistry
Volume66
Issue number20
DOIs
Publication statusPublished - Oct 5 2001

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ASJC Scopus subject areas

  • Organic Chemistry

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