Nucleosides, Nucleotides & Nucleic Acids 2009-05-01

The "Corey's reagent," 3,5-di-tert-butyl-1,2-benzoquinone, as a modifying agent in the synthesis of fluorescent and double-headed nucleosides.

Victor A Timoshchuk, Richard I Hogrefe

Index: Nucleosides Nucleotides Nucleic Acids 28(5) , 464-72, (2009)

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Abstract

A new method for the synthesis of fluorescent nucleosides has been developed. It has been shown that a reaction of benzoquinone with aminopropenyl group at C-5-position of 2'-deoxyuridine or 2'-deoxycytidine and aminopropynyl group at the C-7-position of 8-aza-7-deazaadenosine under extremely mild conditions affords conjugated benzoxazole derivatives of nucleosides, which possess strong fluorescent properties. In a similar reaction 5'-amino-5'-deoxy-nucleosides form double-headed nucleoside derivatives with benzoxazole attached at C-4'-position.