ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The 1H/2H exchange at the methine position of S-[2-(dimethylamino)ethyl] 2-phenylpropanethioate (DEPP) in solvent/D2O mixtures was taken as a model reaction for the metabolic epimerization of 2-arylpropanoyl-coenzyme-A thioesters and was monitored by 1H-NMR spectroscopy at 37°. The solvents used were (D6)acetone, (D3)acetonitrile, (D6)dimethylsulfoxide, and (D5)pyridine. In the investigated range of D2O percentage (10-50%), the exchange reaction was found to increase linearily with D2O content and with the basicity of the organic solvent, the fastest rates being close to 0.09 h-1 (t½ ca. 8 h). These rates are slower than those observed in vivo for the configurational inversion of profens, and they are elicited in totally unphysiological concentrations of bases. The hypothesis thus formulated is that the metabolic epimerization of 2-arylpropanoyl-coenzyme-A thioesters cannot occur nonenzymatically.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19890720606
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