Development of a novel nucleoside analogue with S-type sugar conformation: 2′-deoxy-trans-3′,4′-bridged nucleic acids |
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Authors: | Tomohisa Osaki Yasuki Harada Kensaku Sugaya Somjing Roongjang |
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Institution: | a Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan b PRESTO, JST, 4-1-8 Honcho Kawaguchi, Saitama 332-0012, Japan |
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Abstract: | Two novel trans-3′,4′-bridged nucleic acid (trans-3′,4′-BNA) monomers, one with a 3,5,8-trioxabicyclo5.3.0]decane structure and the other with a 4,7-dioxabicyclo4.3.0]nonane structure, were successfully synthesized from thymidine. The locked trans-fused ring structures of the nucleoside analogues were confirmed by X-ray crystallography, which also indicated that their furanose rings had a typical S-type conformation involving C2′-endo or C3′-exo sugar puckering, respectively, and the same ring conformation as that observed in the B-type helical structure of the DNA duplex. |
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Keywords: | BNA DNA structure mimic Conformation X-ray crystallography |
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