Uridine Diphosphate → Uridine 5'-triphosphate

HRID 217098

Reaction equation

HRID 217098 reaction equation
[P:1]([O:9][CH2:10][C@H:11]1[O:15][C@@H:14]([N:16]2[CH:23]=[CH:22][C:20](=[O:21])[NH:19][C:17]2=[O:18])[C@H:13]([OH:24])[C@@H:12]1[OH:25])([O:4][P:5]([OH:8])([OH:7])=[O:6])(=[O:3])[OH:2].[Cl-].[Mg+2].[Cl-].C(N(CCCC)CCCC)CCC>CN(C)C=O>[CH:22]1[C:20](=[O:21])[NH:19][C:17](=[O:18])[N:16]([C@@H:14]2[O:15][C@H:11]([CH2:10][O:9][P:1]([O:4][P:5]([O:8][P:1]([OH:4])([OH:3])=[O:2])([OH:7])=[O:6])([OH:2])=[O:3])[C@@H:12]([OH:25])[C@H:13]2[OH:24])[CH:23]=1

Participants

5

Reactant 3

HCID 6031Uridine DiphosphateHCID 7622TributylamineHCID 5360315Magnesium Chloride

Product 1

HCID 6133Uridine 5'-triphosphateYield 50.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A 0.154 M dimethylformamide solution of uridine 5′-diphosphate (UDP) tributylamine salt (584 μL, 90.0 μmol) and a 0.45 M dimethylformamide solution of anhydrous magnesium chloride (200 μL, 90.0 μmol) were added to a 0.15 M dimethylformamide solution of cUTP tributylamine salt (500 μL, 75.0 μmol), and the mixture was stirred at room temperature for 72 hours. The resultant reaction mixture was analyzed through HPLC (262 nm). As a result, Up5U (i.e., target product) was found to be produced from UTP at a synthesis yield of 50.5%.

Workup

  1. customThe resultant reaction mixture

Sources & evidence

ORD record
ord-b779d8eddbca477eb784101004ed9b6e
Source dataset
uspto-grants-2012_06
Patent number
US08193338B2

Linked notes

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