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

• Published in: Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2009-05, Vol.28 (5-7), p.464-472
• Main Authors: Timoshchuk, Victor A., Hogrefe, Richard I.
• Format: Article
• Language: English
• Subjects: Benzoquinones - chemical synthesis; Benzoquinones - chemistry; benzoxazoles; Benzoxazoles - chemical synthesis; Benzoxazoles - chemistry; Corey's reagent; double-headed nucleosides; Fluorescent Dyes - chemical synthesis; Fluorescent Dyes - chemistry; Fluorescent nucleosides; labeling; Nucleosides - chemical synthesis; Nucleosides - chemistry
• ISSN: 1525-7770; 1532-2335
• DOI: 10.1080/15257770903044598

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.