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

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