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

Research output: Contribution to journalArticlepeer-review

13 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 languageEnglish
Pages (from-to)2036-2038
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number15
DOIs
Publication statusPublished - 2010 Apr 14

Keywords

  • Artificial deoxyribonucleoside
  • Puckering conformation
  • Transglycosylation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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