Synthesis of oligonucleotides containing thiazole and thiazole N-oxide nucleobases.
[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.
Miller
Tod J
TJ
Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA.
Farquar
Hannah D
HD
Sheybani
Arsham
A
Tallini
Camille E
CE
Saurage
Andrea S
AS
Fronczek
Frank R
FR
Hammer
Robert P
RP
D018360:Crystallography, X-Ray; D008958:Models, Molecular; D009705:Nucleosides / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D013844:Thiazoles / Q000737:chemistry*
D009705:Nucleosides; D009841:Oligonucleotides; D013844:Thiazoles