title: 5-Fluoro-4-thiouridine phosphoramidite: new synthon for introducing photoaffinity label into oligodeoxynucleotides.
abstract: The synthesis of phosphoramidite of 5-fluoro-4-thio-2'-O-methyluridine is described. An appropriate set of protecting groups was optimized including the 4-thio function introduced via 4-triazolyl as the 4-(2-cyanoethyl)thio derivative, and the t-butyldimethyl silyl for 2' and 3' hydroxyl protection, enabling efficient synthesis of the phosphoramidite. These protecting groups prevented unwanted side reactions during oligonucleotide synthesis. The utility of the proposed synthetic route was proven by the preparation of several oligonucleotides via automated synthesis. Photochemical experiments confirmed the utility of the synthon.
authors.affiliation: Adam Mickiewicz University, Faculty of Chemistry, Grunwaldzka 6, 60-780 Poznan, Poland. janmil@amu.edu.pl
authors.forename: Jan
authors.initials: J
authors.lastname: Milecki
authors.forename: Joanna
authors.initials: J
authors.lastname: Nowak
authors.forename: Bohdan
authors.initials: B
authors.lastname: Skalski
authors.forename: Stefan
authors.initials: S
authors.lastname: Franzen
mesh_terms: D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D019920:Photoaffinity Labels / Q000138:chemical synthesis / Q000737:chemistry*; D013891:Thiouridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C548253:5-fluoro-4-thiouridine; D009838:Oligodeoxyribonucleotides; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D019920:Photoaffinity Labels; C434331:phosphoramidite; D013891:Thiouridine