5-azido-deoxyuridine compounds and method of synthesis of...

Details 5-azido-deoxyuridine compounds and method of synthesis of... 5-azido-deoxyuridine compounds and method of synthesis of...

C - Chemistry, Metallurgy

07

H

260/229.3

C07H 19/10 (2006.01)

Patent

CA 1266643

ABSTRACT OF THE DISCLOSURE 5-AZIDO-DEOXYURIDINE COMPOUNDS AND METHOD OF SYNTHESIS OF THE SAME 5-azido-2'-deoxyuridine nucleoside and nucleotide compounds and a method of producing them. The method involves reacting a 5'-deoxyucidine compound with nitrosonium tetrafluocobocate to pro- duce a 5-nitro-deoxyucidine compound. The 5-nitro- deoxyuridine compound is reduced to a 5-amino- deoxyuridine compound in the presence of metallic zinc. The 5-amino-deoxyuridine compound is acidified and reacted with sodium nitrite to produce a 5-diazo- deoxyucidine compound. The diazo-deoxyuridine compound is then reacted with sodium azide to produce a 5-azido-deoxyuridine compound. The latter, in the monophosphate form, is further reacted with diphenylchlorophosphate to produce the photoactive triphosphate, 5-azido-2'-deoxyuridine-5'-triphosphate or 5-azido-dUTP. The photoactive compound, when added to DNA in an in vitro synthesis reaction, pro- duces photoactive DNA.

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