Synthesis and structures of deoxyribonucleoside analogues for triazole-linked DNA (TLDNA)

Tomoko Fujino; Nobuhide Tsunaka; Marine Guillot-Nieckowski; Waka Nakanishi; Takeaki Iwamoto; Eiichi Nakamura; Hiroyuki Isobe

doi:10.1016/j.tetlet.2010.02.046

Synthesis and structures of deoxyribonucleoside analogues for triazole-linked DNA (^TLDNA)

Tomoko Fujino, Nobuhide Tsunaka, Marine Guillot-Nieckowski, Waka Nakanishi, Takeaki Iwamoto, Eiichi Nakamura, Hiroyuki Isobe

SCI - Chemistry

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

Deoxyribonucleoside analogues bearing acetylene group at the pseudo-5′-position and azido group at the pseudo-3′-position have been synthesized by transglycosylation reaction of deoxythymidine analogue with adenine, cytosine, and guanine nucleobases as nucleophiles. The structures of analogues were studied in crystalline state by X-ray crystallography as well as in solution phase by NMR spectroscopy and showed the puckering conformations similar to the natural congeners.

Original language	English
Pages (from-to)	2036-2038
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2010.02.046
Publication status	Published - 2010 Apr 14

Keywords

Artificial deoxyribonucleoside
Puckering conformation
Transglycosylation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2010.02.046

Cite this

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title = "Synthesis and structures of deoxyribonucleoside analogues for triazole-linked DNA (TLDNA)",

abstract = "Deoxyribonucleoside analogues bearing acetylene group at the pseudo-5′-position and azido group at the pseudo-3′-position have been synthesized by transglycosylation reaction of deoxythymidine analogue with adenine, cytosine, and guanine nucleobases as nucleophiles. The structures of analogues were studied in crystalline state by X-ray crystallography as well as in solution phase by NMR spectroscopy and showed the puckering conformations similar to the natural congeners.",

keywords = "Artificial deoxyribonucleoside, Puckering conformation, Transglycosylation",

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note = "Funding Information: This work was partly supported by KAKENHI ( 20655026/20108015 , H.I.). M.G.-N. thanks JSPS for a postdoctoral fellowship. ",

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T1 - Synthesis and structures of deoxyribonucleoside analogues for triazole-linked DNA (TLDNA)

AU - Fujino, Tomoko

AU - Tsunaka, Nobuhide

AU - Guillot-Nieckowski, Marine

AU - Nakanishi, Waka

AU - Iwamoto, Takeaki

AU - Nakamura, Eiichi

AU - Isobe, Hiroyuki

N1 - Funding Information: This work was partly supported by KAKENHI ( 20655026/20108015 , H.I.). M.G.-N. thanks JSPS for a postdoctoral fellowship.

PY - 2010/4/14

Y1 - 2010/4/14

N2 - Deoxyribonucleoside analogues bearing acetylene group at the pseudo-5′-position and azido group at the pseudo-3′-position have been synthesized by transglycosylation reaction of deoxythymidine analogue with adenine, cytosine, and guanine nucleobases as nucleophiles. The structures of analogues were studied in crystalline state by X-ray crystallography as well as in solution phase by NMR spectroscopy and showed the puckering conformations similar to the natural congeners.

AB - Deoxyribonucleoside analogues bearing acetylene group at the pseudo-5′-position and azido group at the pseudo-3′-position have been synthesized by transglycosylation reaction of deoxythymidine analogue with adenine, cytosine, and guanine nucleobases as nucleophiles. The structures of analogues were studied in crystalline state by X-ray crystallography as well as in solution phase by NMR spectroscopy and showed the puckering conformations similar to the natural congeners.

KW - Artificial deoxyribonucleoside

KW - Puckering conformation

KW - Transglycosylation

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