Concepedia

Synthesis and properties of novel 2′-C,4′-C-ethyleneoxy-bridged 2′-deoxyribonucleic acids with exocyclic methylene groups

Takashi Osawa, Satoshi Obika, Yoshiyuki Hari

Organic & Biomolecular Chemistry · 2016 · 27 citations · 25 references

DOI

Concepts

Abstract

Three 2'-C,4'-C-ethyleneoxy-bridged 2'-deoxyribonucleic acids possessing six-membered bridges with 6'-oxygen and 8'-exocyclic methylene groups (methylene-EoDNAs) were designed and synthesized in nine to ten steps from 5-methyluridine. The methylene-EoDNA-modified oligonucleotides showed excellent binding affinity with target ssRNA and extremely high nuclease resistance compared with natural oligonucleotides. These results proved the potential of methylene-EoDNAs for nucleic acid based technology.

References

25

Duplexes of 21-nucleotide RNAs mediate RNA interference in cultured mammalian cells

Sayda M. Elbashir, Jens Harborth, Winfried Lendeckel et al. · Nature · 2001 · 9.4K citations

, , +7

LNA (Locked Nucleic Acids): Synthesis of the adenine, cytosine, guanine, 5-methylcytosine, thymine and uracil bicyclonucleoside monomers, oligomerisation, and unprecedented nucleic acid recognition

Alexei A. Koshkin, Sanjay K. Singh, Poul Nielsen et al. · Tetrahedron · 1998 · 1K citations

, , +16

LNA (locked nucleic acids): synthesis and high-affinity nucleic acid recognition

Sanjay K. Singh, Alexei A. Koshkin, Jesper Wengel et al. · Chemical Communications · 1998 · 770 citations

, , +16

Stability and structural features of the duplexes containing nucleoside analogues with a fixed N-type conformation, 2′-O,4′-C-methyleneribonucleosides

Satoshi Obika, Daishu Nanbu, Yoshiyuki Hari et al. · Tetrahedron Letters · 1998 · 693 citations

, , +16

Synthesis of 2′-O,4′-C-methyleneuridine and -cytidine. Novel bicyclic nucleosides having a fixed C3, -endo sugar puckering

Satoshi Obika, Daishu Nanbu, Yoshiyuki Hari et al. · Tetrahedron Letters · 1997 · 601 citations

, , +13