Synthesis of an enantiomeric DNA oligomer and its T-HgII-T base-pair formation.

Kaichiro Haruta; Yoshiyuki Tanaka; Takuya Kawamura; Yoshinori Kondo; Akira Ono; Hiroyuki Yamakoshi; Naoki Kanoh; Yoshiharu Iwabuchi

doi:10.1093/nass/nrm094

Synthesis of an enantiomeric DNA oligomer and its T-HgII-T base-pair formation.

Kaichiro Haruta, Yoshiyuki Tanaka, Takuya Kawamura, Yoshinori Kondo, Akira Ono, Hiroyuki Yamakoshi, Naoki Kanoh, Yoshiharu Iwabuchi

PHA - Molecular Pharmaceutical Science

Research output: Contribution to journal › Article

Abstract

Unnatural "L-DNA" containing 2'-deoxy-L-ribose backbone instead of natural 2'-deoxy-D-ribose was synthesized and evaluated by (1)H NMR, CD spectra. Proton ((1)H) NMR spectra of natural DNA (D-TpT) and L-DNA (L-TpT) are fully consistent with each other. In CD spectra, however, spectrum of L-TpT was reversed, relative to that of D-TpT. These results indicate that L-TpT is an isomer with a mirror image configuration of D-TpT. In summary, we have synthesized enantiomeric L-DNA, and the L-DNA would be materials for nanodevices and tools for exploring why the D-isomer of DNA molecules was selected as a bio-molecule.

Original language	English
Pages (from-to)	187-188
Number of pages	2
Journal	Nucleic acids symposium series (2004)
Issue number	51
DOIs	https://doi.org/10.1093/nass/nrm094
Publication status	Published - 2007

ASJC Scopus subject areas

Medicine(all)

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10.1093/nass/nrm094

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Haruta, K., Tanaka, Y., Kawamura, T., Kondo, Y., Ono, A., Yamakoshi, H., Kanoh, N., & Iwabuchi, Y. (2007). Synthesis of an enantiomeric DNA oligomer and its T-HgII-T base-pair formation. Nucleic acids symposium series (2004), (51), 187-188. https://doi.org/10.1093/nass/nrm094

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title = "Synthesis of an enantiomeric DNA oligomer and its T-HgII-T base-pair formation.",

abstract = "Unnatural {"}L-DNA{"} containing 2'-deoxy-L-ribose backbone instead of natural 2'-deoxy-D-ribose was synthesized and evaluated by (1)H NMR, CD spectra. Proton ((1)H) NMR spectra of natural DNA (D-TpT) and L-DNA (L-TpT) are fully consistent with each other. In CD spectra, however, spectrum of L-TpT was reversed, relative to that of D-TpT. These results indicate that L-TpT is an isomer with a mirror image configuration of D-TpT. In summary, we have synthesized enantiomeric L-DNA, and the L-DNA would be materials for nanodevices and tools for exploring why the D-isomer of DNA molecules was selected as a bio-molecule.",

author = "Kaichiro Haruta and Yoshiyuki Tanaka and Takuya Kawamura and Yoshinori Kondo and Akira Ono and Hiroyuki Yamakoshi and Naoki Kanoh and Yoshiharu Iwabuchi",

year = "2007",

doi = "10.1093/nass/nrm094",

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pages = "187--188",

journal = "Nucleic acids symposium series (2004)",

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T1 - Synthesis of an enantiomeric DNA oligomer and its T-HgII-T base-pair formation.

AU - Haruta, Kaichiro

AU - Tanaka, Yoshiyuki

AU - Kawamura, Takuya

AU - Kondo, Yoshinori

AU - Ono, Akira

AU - Yamakoshi, Hiroyuki

AU - Kanoh, Naoki

AU - Iwabuchi, Yoshiharu

PY - 2007

Y1 - 2007

N2 - Unnatural "L-DNA" containing 2'-deoxy-L-ribose backbone instead of natural 2'-deoxy-D-ribose was synthesized and evaluated by (1)H NMR, CD spectra. Proton ((1)H) NMR spectra of natural DNA (D-TpT) and L-DNA (L-TpT) are fully consistent with each other. In CD spectra, however, spectrum of L-TpT was reversed, relative to that of D-TpT. These results indicate that L-TpT is an isomer with a mirror image configuration of D-TpT. In summary, we have synthesized enantiomeric L-DNA, and the L-DNA would be materials for nanodevices and tools for exploring why the D-isomer of DNA molecules was selected as a bio-molecule.

AB - Unnatural "L-DNA" containing 2'-deoxy-L-ribose backbone instead of natural 2'-deoxy-D-ribose was synthesized and evaluated by (1)H NMR, CD spectra. Proton ((1)H) NMR spectra of natural DNA (D-TpT) and L-DNA (L-TpT) are fully consistent with each other. In CD spectra, however, spectrum of L-TpT was reversed, relative to that of D-TpT. These results indicate that L-TpT is an isomer with a mirror image configuration of D-TpT. In summary, we have synthesized enantiomeric L-DNA, and the L-DNA would be materials for nanodevices and tools for exploring why the D-isomer of DNA molecules was selected as a bio-molecule.

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