Synthesis of oligonucleotides containing thiazole and thiazole N-oxide nucleobases

Tod J. Miller, Hannah D. Farquar, Arsham Sheybani, Camille E. Tallini, Andrea S. Saurage, Frank R. Fronczek, Robert P. Hammer

Research output: Contribution to journalArticle

9 Scopus citations

Abstract

(equation presented) 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.

Original languageEnglish
Pages (from-to)877-880
Number of pages4
JournalOrganic Letters
Volume4
Issue number6
DOIs
StatePublished - Mar 21 2002
Externally publishedYes

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    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), 877-880. https://doi.org/10.1021/ol017003g