One-pot synthesis of modified DNA oligomers by novel glycosidation using nucleic acids

Kazunobu Toshima, Yuichi Nishikubo, Shuichi Matsumura

Research output: Contribution to conferencePaper

Abstract

We demonstrate the novel glycosidations using a nucleic acid base (A or G) as a leaving group of glycosyl donors and the one-pot synthesis of modified DNA oligomers using this glycosidation method. It was found that the glycosidations of guanosine and adenosine with alcohols using MeOTf as an alkylative agent or TfOH as a protic acid in DMSO effectively proceeded to give the corresponding glycosides in high yields, while cytidine and thymidine could not be activated under these conditions. Furthermore, it was found that DNA oligomers could be converted into DNA oligomer analogs, which were selectively modified at the purine base positions, by this glycosidation method in one step.

Original languageEnglish
Pages5077-5078
Number of pages2
Publication statusPublished - 2005 Dec 1
Event54th SPSJ Symposium on Macromolecules - Yamagata, Japan
Duration: 2005 Sep 202005 Sep 22

Other

Other54th SPSJ Symposium on Macromolecules
CountryJapan
CityYamagata
Period05/9/2005/9/22

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Keywords

  • DNA
  • Glycosidation
  • Glycoside
  • Modified DNA oligomer
  • One-pot synthesis

ASJC Scopus subject areas

  • Engineering(all)

Cite this

Toshima, K., Nishikubo, Y., & Matsumura, S. (2005). One-pot synthesis of modified DNA oligomers by novel glycosidation using nucleic acids. 5077-5078. Paper presented at 54th SPSJ Symposium on Macromolecules, Yamagata, Japan.