New synthesis of 5-carboxy-2'-deoxyuridine and its incorporation into synthetic oligonucleotides.
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.
Guerniou
V
V
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.
Gasparutto
D
D
Sauvaigo
S
S
Favier
A
A
Cadet
J
J
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
D000577:Amides; D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D010756:Phosphoric Acids; C017107:5-carboxy-2'-deoxyuridine; C011067:phosphoramidic acid; D003857:Deoxyuridine