2-(5-Hexenylthio)adenosine 5'-triphosphate → 2-(5-Hexenylthio) adenosine 5'-diphosphate trisammonium salt

HRID 53475Notes

Reaction equation

HRID 53475 reaction equation
[NH4+:1].[NH4+].[NH4+].[NH4+].[P:5]([O:17][CH2:18][C@H:19]1[O:23][C@@H:22]([N:24]2[C:33]3[N:32]=[C:31]([S:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH2:40])[N:30]=[C:28]([NH2:29])[C:27]=3[N:26]=[CH:25]2)[C@H:21]([OH:41])[C@@H:20]1[OH:42])([O:8][P:9]([O:12]P([O-])([O-])=O)([O-:11])=[O:10])(=[O:7])[O-:6].P(OC[C@H]1O[C@@H]([N:62]2C3N=C(SCCCCC=C)N=C(N)C=3N=C2)[C@H](O)[C@@H]1O)(OP(OP(O)(O)=O)(O)=O)(=O)O>>[NH4+:24].[NH4+:62].[NH4+:1].[P:5]([O:17][CH2:18][C@H:19]1[O:23][C@@H:22]([N:24]2[C:33]3[N:32]=[C:31]([S:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=[CH2:40])[N:30]=[C:28]([NH2:29])[C:27]=3[N:26]=[CH:25]2)[C@H:21]([OH:41])[C@@H:20]1[OH:42])([O:8][P:9]([O-:11])([O-:12])=[O:10])(=[O:6])[O-:7]

Participants

3

Reactant 2

HCID 228718472-(5-Hexenylthio)adenosine 5'-triphosphateHCID 228718482-(5-Hexenylthio)adenosine 5'-triphosphate tetraammonium salt

Product 1

HCID 867506982-(5-Hexenylthio) adenosine 5'-diphosphate trisammonium salt

Procedure

NMR of 2-(5-hexenylthio)adenosine 5'-triphosphate tetraammonium salt: 1H NMR (D2) d: 8.41 (S, 1H, H-8), 6.13 (d, J=5.7 Hz, 1H, H-1'), 4.64 (m, 1H, H-3'), 4.37 (m, 1H, H-4'), 4.24 (din, 2H, H-5'). High Res. FAB: calcd. for C16H25O13N5P3S: 620.0382. Found: 620.0428. Retention time: 7.7 min (91% purity) using solvent system I, 7.4 min (>98% purity) using solvent system II. 2-(5-Hexenylthio)adenosine 5'-triphosphate was also synthesized by the triphosphorylation procedure recited in Example 1.

Workup

  1. customsolvent system I, 7.4 min (>98% purity)

Sources & evidence

ORD record
ord-4793d58f7cc5434ca4f47852a0b25bcd
Source dataset
uspto-grants-1997_04
Patent number
US05620676

Reaction notes

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