Reaktionsgleichung
[N:1]1[CH:9]=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.CP(=O)([O-])[O-].C[C@H](NC(CC1C=C(F)C=C(F)C=1)=O)C([NH:19][C@H](C(OC(C)(C)C)=O)C1C=CC=CC=1)=O.C(N(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O)CN(CC([O-])=O)CC([O-])=O.[OH-].[NH4+]>Cl>[N:1]1[C:9]([NH2:19])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Purine-containing oligonucleoside methylphosphonates may be depurinated by treatment by hydrochloric acid at 65° C. The methylphosphonate linkage is resistant to hydrolysis by these conditions as shown by the stability of d-TpT and d-TpTpT. On the other hand, dimers or trimers containing purine bases such as d-ApA, dApT, dTpA or d-ApApA have half-lives between 92 and 144 min in 0.01 M hydrochloric acid. Following neutralization with ammonium hydroxide, the products of these reactions were characterized by reversed phase HPLC. d-ApA gave adenine, while both d-ApT and d-TpA gave adenine and thymidine as the sole products of the reaction. Adenine and d-ApA were the only products observed when d-ApApA was partially hydrolyzed. When d-CpCpApT was completely hydrolyzed in acid three products, d-CpC, adenine and thymidine, were observed in a molar ratio of 1:1:1.
Quellen und Nachweise
- ORD-Eintrag
- ord-2c1a88d248204ed3a1b95077e24c5be4
- Quelldatensatz
- uspto-grants-1985_03
- Patentnummer
- US04507433
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