Novel conformationally constrained 2′-C-methylribonucleosides: synthesis and incorporation into oligonucleotides
K Vejlegaard, C Wegeberg, V McKee… - Organic & Biomolecular …, 2018 - pubs.rsc.org
Organic & Biomolecular Chemistry, 2018•pubs.rsc.org
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 …
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 …
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.
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