New synthesis of 5-carboxy-2'-deoxyuridine and its incorporation into synthetic oligonucleotides

  • Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):1073-5. doi: 10.1081/NCN-120022739.
V Guerniou  1 ,  D Gasparutto ,  S Sauvaigo ,  A Favier ,  J Cadet
Affiliations
  • 1. Laboratoire Lésions des Acides Nucléiques, Service de Chimie Inorganique et Biologique, UMR 5046, CEA/DSM/Departement de Recherche Fondamentale sur la Matière Condensée, Grenoble Cedex, France.
PMID: 14565347 DOI: 10.1081/NCN-120022739
Abstract

5-Carboxy-2'-deoxyuridine is a methyl oxidation product of thymidine. It can be formed by the menadione-mediated photosensitization of thymidine in aerated aqueous solution. Here in we present a new four-step synthesis of the 5-carboxy-2'-deoxyuridine phosphoramidite building block based on the alkaline hydrolysis of 5-trifluoromethyl-2'-deoxyuridine. The phosphoramidite derivative has been incorporated at defined sites into oligonucleotides using the solid phase synthesis approach.

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