title: New synthesis of 5-carboxy-2'-deoxyuridine and its incorporation into synthetic oligonucleotides.
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.
authors.affiliation: 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.
authors.forename: V
authors.initials: V
authors.lastname: Guerniou
authors.forename: D
authors.initials: D
authors.lastname: Gasparutto
authors.forename: S
authors.initials: S
authors.lastname: Sauvaigo
authors.forename: A
authors.initials: A
authors.lastname: Favier
authors.forename: J
authors.initials: J
authors.lastname: Cadet
mesh_terms: D000577:Amides; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D010756:Phosphoric Acids
chemical_list: D000577:Amides; D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D010756:Phosphoric Acids; C017107:5-carboxy-2'-deoxyuridine; C011067:phosphoramidic acid; D003857:Deoxyuridine