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.
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.
Timoshchuk
Victor A
VA
TriLink Biotechnologies, Inc., San Diego, California, USA. vtimoshchuk@trilinkbiotech.com
Hogrefe
Richard I
RI
D016227:Benzoquinones / Q000138:chemical synthesis / Q000737:chemistry*; D001583:Benzoxazoles / Q000138:chemical synthesis / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
D016227:Benzoquinones; D001583:Benzoxazoles; D005456:Fluorescent Dyes; D009705:Nucleosides; C054466:3,5-di-tert-butyl-1,2-benzoquinone