Title
Synthesis of oligonucleotides containing thiazole and thiazole N-oxide nucleobases
Document Type
Article
Publication Date
3-21-2002
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.
Publication Source (Journal or Book title)
Organic letters
First Page
877
Last Page
80
Recommended Citation
Miller, T. J., Farquar, H. D., Sheybani, A., Tallini, C. E., Saurage, A. S., Fronczek, F. R., & Hammer, R. P. (2002). Synthesis of oligonucleotides containing thiazole and thiazole N-oxide nucleobases. Organic letters, 4 (6), 877-80. https://doi.org/10.1021/ol017003g