Synthesis and chemical properties of a novel 2',4'-bridged nucleic acid analogue with a seven-membered cyclic carbamate structure | Zendy

M. Nishida | Zendy; Tetsuya Kodama | Zendy; Satoshi Obika | Zendy; Tadashi Imanishi | Zendy

Open Access

Synthesis and chemical properties of a novel 2',4'-bridged nucleic acid analogue with a seven-membered cyclic carbamate structure

Author(s) -

M. Nishida,

Tetsuya Kodama,

Satoshi Obika,

Tadashi Imanishi

Publication year - 2007

Publication title -

nucleic acids symposium series

Language(s) - English

Resource type - Journals

eISSN - 1746-8272

pISSN - 0261-3166

DOI - 10.1093/nass/nrm079

Subject(s) - carbamate , furanose , monomer , nucleic acid , moiety , chemistry , chemical structure , stereochemistry , chemical shift , molecule , crystallography , organic chemistry , ring (chemistry) , polymer , biochemistry

BNA We designed and synthesized a novel bridged nucleic acid (BNA) with N-type sugar conformation, possessing a seven-membered cyclic carbamate structure (2',4'-(CNC) monomer). The monomer shows interesting chemical properties, such as prompt migration of the carbamate bridge from the 2'-to the 3'-position and consequent conformational change of the furanose moiety. These chemical behaviors of 2',4'-BNA(CNC) were investigated by (1)H-NMR analysis, and the structure of the compound after migration was confirmed by X-ray crystallographic analysis.

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