Triethylamine → Deoxyuridine Triphosphate

HRID 1976945Notes

Reaction equation

HRID 1976945 reaction equation
[P:1]([O:13][CH2:14][C@H:15]1[O:19][C@@H:18]([N:20]2[CH:27]=[C:26](CC=CN)[C:24](=[O:25])[NH:23][C:21]2=[O:22])[CH2:17][C@@H:16]1[OH:32])([O:4][P:5]([O:8][P:9]([OH:12])([OH:11])=[O:10])([OH:7])=[O:6])(=[O:3])[OH:2].C(N(CC)CC)C>O.CN(C=O)C>[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])[CH2:17][C@@H:16]1[OH:32])([O:4][P:5]([O:8][P:9]([OH:11])([OH:12])=[O:10])([OH:7])=[O:6])(=[O:2])[OH:3]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 865993805-(3-Amino)allyldeoxyuridine 5'-triphosphate

Product 1

HCID 65070Deoxyuridine Triphosphate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2 mg of 5-(3-aminoallyl)-2′-deoxyuridine-5′-triphosphate, ammonium salt (Sigma Chemical) in 100 μL of water is added a solution of 3 mg of Compound 72 (Example 73) in 100 μL of DMF, followed by addition of 5 μL of triethylamine. After the mixture is stirred at room temperature for 3 hours, the solution is evaporated to dryness under vacuum and the residue is purified by chromatography over lipophilic SEPHADEX resin using water for elution. The first green fluorescent fractions are combined and lyophilized to give the fluorescent nucleotide conjugate as an orange solid (Compound 107) Alternatively a fluorescent conjugate (Compound 108) of deoxyuridine-5′-triphosphate is prepared using 5-(3-amino-1-propynyl)-2′-deoxyuridine-5′-triphosphate in place of 5-(3-aminoally)-2′-deoxyuridine-5′-triphosphate (as described in Hobbs, Jr. et al, supra).

Workup

  1. customthe solution is evaporated to dryness under vacuum
  2. customthe residue is purified by chromatography over lipophilic SEPHADEX resin
  3. washfor elution

Sources & evidence

ORD record
ord-34546c0d15c847888c723c0442c97165
Source dataset
uspto-grants-2001_05
Patent number
US06229055B1

Reaction notes

Loading…