Novel conformationally constrained 2′-C-methylribonucleosides: synthesis and incorporation into oligonucleotides?

Organic & Biomolecular Chemistry Pub Date: 2018-01-24 DOI: 10.1039/C7OB02663C

Abstract

Synthesis of two novel conformationally constrained bicyclic ribonucleoside phosphoramidites bearing a 2′-C-methyl substituent has been accomplished. These phosphoramidites were used to incorporate the corresponding 2′-C-methyl nucleotides into oligonucleotides and to study their effects on duplex thermal stability. Whereas the C2′–O4′-linked LNA-type derivative induced severe destabilization of duplexes formed with complementary DNA and RNA, the C3′–O4′-linked derivative induced RNA-selective hybridization with increased affinity relative to that of the unmodified DNA-based probe.

Graphical abstract: Novel conformationally constrained 2′-C-methylribonucleosides: synthesis and incorporation into oligonucleotides
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