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

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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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Publication details

The article was received on 30 Oct 2017, accepted on 24 Jan 2018 and first published on 24 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB02663C
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Novel conformationally constrained 2′-C-methylribonucleosides: synthesis and incorporation into oligonucleotides

    K. Vejlegaard, C. Wegeberg, V. McKee and J. Wengel, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C7OB02663C

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