Ddctp → N4-(3-Aminopropyl)-2',3'-dideoxycytidine-5'-triphosphate

HRID 1534972Notes

Reaction equation

HRID 1534972 reaction equation
[OH:1][P:2](=[O:27])([O:12][CH2:13][C@H:14]1[O:26][C@@H:17]([N:18]2[CH:23]=[CH:22][C:21]([NH2:24])=[N:20][C:19]2=[O:25])[CH2:16][CH2:15]1)[O:3][P:4](=[O:11])([O:6][P:7](=[O:10])([OH:9])[OH:8])[OH:5]>O>[P:2]([O:12][CH2:13][C@H:14]1[O:26][C@@H:17]([N:18]2[CH:23]=[CH:22][C:21]([NH:24][CH2:15][CH2:16][CH2:17][NH2:18])=[N:20][C:19]2=[O:25])[CH2:16][CH2:15]1)([O:3][P:4]([O:6][P:7]([OH:9])([OH:8])=[O:10])([OH:5])=[O:11])(=[O:1])[OH:27]

Participants

3

Reactant 1

HCID 119119Ddctp2×

Product 1

HCID 86745505N4-(3-Aminopropyl)-2',3'-dideoxycytidine-5'-triphosphate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2',3'-dideoxycytidine-5'-triphosphate (20 umol) was dissolved in 1.0 ml of the 1,3-propanediamine/bisulfite reaction mixture and incubated at 37° C. for 60 hr. when HPLC indicated complete conversion of the starting material to one new major substance. The product was isolated by Sephadex chromatography and lyophilization in the manner described above to yield 16.0 umol (80%) of an amorphous solid and identified as N4 -(3-aminopropyl)-2'3'-dideoxycytidine-5-triphosphate AP-ddCTP. The structure of AP-ddCTP is depicted in FIG. 1 as B where N equals three. The solid was homogeneous by HPLC (RT=20.02 min, RT(ddCTP)=21.08) and characterized by UV lambda max (H2O)=272.5 nm.

Sources & evidence

ORD record
ord-71131729721f4550b0be61c6c000a902
Source dataset
uspto-grants-1992_02
Patent number
US05091519

Reaction notes

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