Unit

UNIT 1.21 Synthesis of 5-Formyl-2′-Deoxyuridine and Its Incorporation into Oligodeoxynucleotides

  1. Kousuke Sato,
  2. Wataru Hirose,
  3. Akira Matsuda

Published Online: 1 DEC 2008

DOI: 10.1002/0471142700.nc0121s35

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Sato, K., Hirose, W. and Matsuda, A. 2008. Synthesis of 5-Formyl-2′-Deoxyuridine and Its Incorporation into Oligodeoxynucleotides. Current Protocols in Nucleic Acid Chemistry. 35:1.21:1.21.1–1.21.19.

Author Information

  1. Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan

Publication History

  1. Published Online: 1 DEC 2008
  2. Published Print: DEC 2008

Abstract

A straightforward, efficient method for the synthesis of 5-formyl-2′-deoxyuridine (dfU) and solid-phase synthesis of oligodeoxynucleotides containing dfU using a phosphoramidite method are described. The synthesis of dfU is achieved by oxidation of the 5-methyl group in thymidine derivatives. However, incorporation of the dfU 3′-O-phosphoramidite into oligodeoxynucleotides proceeds in low yield, due to instability of the 5-formyl group under conditions used for automated DNA synthesis. Therefore, oligodeoxynucleotides containing a 5-(1,2-dihydroxyethyl)uracil derivative are first prepared and finally oxidized by periodate to give the desired oligodeoxynucleotides containing 5-formyluracil. Curr. Protoc. Nucleic Acid Chem. 35:1.21.1-1.21.19. © 2008 by John Wiley & Sons, Inc.

Keywords:

  • 5-formyl-2′-deoxyuridine;
  • thymidine;
  • oligodeoxynucleotide;
  • oxidation;
  • oxidative damage;
  • chemical synthesis