Direct and practical synthesis of 2′-O,4′-C-aminomethylene-bridged nucleic acid purine derivatives by transglycosylation

Purine nucleosides of 2′-O,4′-C-aminomethylene-bridged nucleic acid (BNANC) have been directly synthesized from pyrimidine BNANC using transglycosylation reaction with high stereoselectivity and excellent yield. The BNANC purine nucleosides (adenosine, guanosine, and inosine) prepared by the direct...

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Bibliographic Details
Published inTetrahedron Vol. 73; no. 9; pp. 1211 - 1218
Main Authors Umemoto, Tadashi, Masada, Shinichi, Miyata, Kenichi, Ogasawara-Shimizu, Mari, Murata, Shumpei, Nishi, Kazunori, Ogi, Kazuhiro, Hayase, Yoji, Cho, Nobuo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 02.03.2017
Elsevier
Subjects
Chemistry
Chemistry, Organic
LNA/2′,4′-BNA
Modified nucleic acids
Oligonucleotides
Physical Sciences
Science & Technology
Transglycosylation
Transglycosylation
Modified nucleic acids
LNA/2′,4′-BNA
Oligonucleotides
RNA
5-METHYLCYTOSINE
2'-AMINO-LNA
NUCLEOSIDES
THYMINE
LNA/2 ',4 '-BNA
SCALE SYNTHESIS
IN-VITRO
ALPHA-L-LNA
ADENINE
SELECTION
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Summary:Purine nucleosides of 2′-O,4′-C-aminomethylene-bridged nucleic acid (BNANC) have been directly synthesized from pyrimidine BNANC using transglycosylation reaction with high stereoselectivity and excellent yield. The BNANC purine nucleosides (adenosine, guanosine, and inosine) prepared by the direct and practical procedure were derivatized to the corresponding phosphoramidites and were incorporated into DNA. A thermal denaturation study showed that BNANC-containing oligonucleotides hybridized to RNA selectively with excellent mismatch discrimination. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.01.010