title: Synthesis of oligonucleotides containing thiazole and thiazole N-oxide nucleobases.
abstract: [reaction: see text] The thiazole C-nucleoside analogue was synthesized by the Hantzsch cyclization method to form the thiazole ring and was then converted to the thiazole N-oxide C-nucleoside analogue by peracid oxidation of the heterocycle nitrogen. Incorporation of the thiazole and thiazole N-oxide phosphoramidites into DNA was successful though significant deoxygenation of the N-oxide occurred during DNA assembly. The mechanism proposed for the reduction of the thiazole N-oxide to thiazole involves the formation of an N-oxide phosphite ester.
authors.affiliation: Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA.
authors.forename: Tod J
authors.initials: TJ
authors.lastname: Miller
authors.forename: Hannah D
authors.initials: HD
authors.lastname: Farquar
authors.forename: Arsham
authors.initials: A
authors.lastname: Sheybani
authors.forename: Camille E
authors.initials: CE
authors.lastname: Tallini
authors.forename: Andrea S
authors.initials: AS
authors.lastname: Saurage
authors.forename: Frank R
authors.initials: FR
authors.lastname: Fronczek
authors.forename: Robert P
authors.initials: RP
authors.lastname: Hammer
mesh_terms: D018360:Crystallography, X-Ray; D008958:Models, Molecular; D009705:Nucleosides / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D013844:Thiazoles / Q000737:chemistry*
chemical_list: D009705:Nucleosides; D009841:Oligonucleotides; D013844:Thiazoles