5-azido-deoxyuridine compounds and method of synthesis of the same
US4672111A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Apr 23, 1985 |
| Grant date | Jun 9, 1987 |
| Priority date | — |
| Expiry date | Apr 23, 2005 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H19/10
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
5-azido-2-'-deoxyuridine nucleoside and nucleotide compounds and a method of producing them. The method involves reacting a 5'-deoxyuridine compound with nitrosonium tetrafluoroborate to produce a 5-nitro-deoxyuridine 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-deoxyuridine 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, produces photoactive DNA.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.