trans-3',4'-BNAs, novel nucleic acid analogues with an S-type conformation: synthesis and incorporation into oligonucleotides

Mitsuaki Sekiguchi; Tomohisa Osaki; Yasuki Harada; Satoshi Obika; Takeshi Imanishi

doi:10.1093/nass/3.1.111

trans-3',4'-BNAs, novel nucleic acid analogues with an S-type conformation: synthesis and incorporation into oligonucleotides

Nucleic Acids Res Suppl. 2003:(3):111-2. doi: 10.1093/nass/3.1.111.

Authors

Mitsuaki Sekiguchi¹, Tomohisa Osaki, Yasuki Harada, Satoshi Obika, Takeshi Imanishi

Affiliation

¹ Graduate School of Phamaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.

PMID: 14510405
DOI: 10.1093/nass/3.1.111

Abstract

We designed and successfully synthesized novel nucleic acid analogues with a C3'-C4' trans-fused six-membered ring, trans-3',4'-BNAs from D-glucose. A 1H-NMR experiment and X-ray crystallographic analysis demonstrated that the sugar puckering of trans-3',4'-BNA was restricted in an S-type conformation. We also achieved its incorporation into oligonucleotides using automated DNA synthesizer.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Nucleic Acid Conformation
Nucleic Acids / chemical synthesis*
Nucleic Acids / chemistry
Oligonucleotides / chemistry*
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

Nucleic Acids
Oligonucleotides