5-Amino-2'-deoxyuridine → 5-Diazo-deoxyuridine

HRID 652465

Reaktionsgleichung

Reaktionsgleichung von HRID 652465
[N+:1]([C:4]1[C:5](=[O:19])[NH:6][C:7](=[O:18])[N:8]([CH:17]=1)[C@@H:9]1[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[CH2:10]1)([O-])=O.[NH2:20]C1C(=O)NC(=O)N(C=1)[C@@H]1O[C@H](CO)[C@@H](O)C1.N([O-])=O.[Na+]>[Zn]>[N+:1](=[C:4]1[CH2:17][N:8]([C@@H:9]2[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[CH2:10]2)[C:7](=[O:18])[NH:6][C:5]1=[O:19])=[N-:20]

Komponenten

5

Edukt 3

HCID 1110815-Amino-2'-deoxyuridineHCID 1456815-Nitro-2'-deoxyuridine2×HCID 23668193Sodium Nitrite

Produkt 1

HCID 186082155-Diazo-deoxyuridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23994ZincKatalysator

Versuchsvorschrift

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.

Quellen und Nachweise

ORD-Eintrag
ord-82695b5708c246feb04fc023f91e9549
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04672111

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