Iodine → HCID 131721381, compound

HRID 618965Notes

Reaction equation

HRID 618965 reaction equation
[P:1]([O:13][CH2:14][C@H:15]1[O:19][C@@H:18]([N:20]2[CH:27]=[CH:26][C:24](=[O:25])[NH:23][C:21]2=[O:22])[C@H:17]([NH2:28])[C@@H:16]1[OH:29])([O:4][P:5]([O:8][P:9]([O-:12])([O-:11])=[O:10])([O-:7])=[O:6])(=[O:3])[O-:2].[CH2:30]([NH+:32]([CH2:35][CH3:36])[CH2:33][CH3:34])[CH3:31].[CH2:37]([NH+:39]([CH2:42][CH3:43])[CH2:40][CH3:41])[CH3:38].[CH2:44]([NH+:46]([CH2:49][CH3:50])[CH2:47][CH3:48])[CH3:45].[CH2:51]([NH+:53]([CH2:56][CH3:57])[CH2:54][CH3:55])[CH3:52].[I:58]I>C([O-])(=O)C.[Na+].C(O)C>[P:1]([O:13][CH2:14][C@H:15]1[O:19][C@@H:18]([N:20]2[CH:27]=[C:26]([I:58])[C:24](=[O:25])[NH:23][C:21]2=[O:22])[C@H:17]([NH2:28])[C@@H:16]1[OH:29])([O:4][P:5]([O:8][P:9]([O-:11])([O-:12])=[O:10])([O-:7])=[O:6])(=[O:2])[O-:3].[CH2:30]([NH+:32]([CH2:35][CH3:36])[CH2:33][CH3:34])[CH3:31].[CH2:37]([NH+:39]([CH2:42][CH3:43])[CH2:40][CH3:41])[CH3:38].[CH2:44]([NH+:46]([CH2:49][CH3:50])[CH2:47][CH3:48])[CH3:45].[CH2:51]([NH+:53]([CH2:56][CH3:57])[CH2:54][CH3:55])[CH3:52]

Participants

5

Reactant 2

HCID 807IodineHCID 131721382HCID 131721382, compound

Product 1

HCID 131721381HCID 131721381, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 517045Sodium AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of tetrakis(triethylammonium)-2'-amino,2'-deoxyuridine 5'-triphosphate (35.2 mg, 0.02 mmoles, 0.02M) in sodium acetate (0.1M, 2 ml, pH 6.0) was added a solution of mercuric acetate (63.74 mg in 0.1M sodium acetate, 0.01M). The mixture was heated at 50° C. for 3 h. After cooling to room temperature, a solution of iodine in ethanol (25.38 mg I2 in 80 μl ethanol) was added. The mixture was stirred at room temperature in the dark for 1 h. The product was purified by DEAE Sephadex-A25 (Pharmacia) chromatography (0-1M triethyl ammonium bicarbonate buffer). To remove excess buffer salt the product was repeatedly concentrated from methanol to yield 6 mg (30%) tetrakis(triethylammonium)-5-iodo,2'-amino,2'-deoxyuridine 5'-triphosphate. UV: λmax 273 nm.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe product was purified by DEAE Sephadex-A25 (Pharmacia) chromatography (0-1M triethyl ammonium bicarbonate buffer)
  3. customTo remove excess buffer salt the product
  4. concentrationwas repeatedly concentrated from methanol

Sources & evidence

ORD record
ord-226c7cd4421c4289b2f4b64800060b65
Source dataset
uspto-grants-1999_09
Patent number
US05958691

Reaction notes

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