PMID:2306109
| Citation |
Brewer, F, Seim, H and Englard, S (1990) Reexamination of the 1H NMR assignments and solution conformations of L-carnitine and O-acetyl-L-carnitine using C-2 stereospecifically labeled monodeuterated isomers. Arch. Biochem. Biophys. 276:495-9 |
|---|---|
| Abstract |
The two C-2 monodeuterated isomers of L-carnitine were synthesized by enzymatic hydration of crotonobetaine in D2O and by enzymatic proton exchange of L-[2-2H2]carnitine in H2O. These reactions, catalyzed by an induced Escherichia coli carnitine hydrolyase proceed stereospecifically. The two isomers of L-[2-2H]carnitine were examined by 1H NMR at 500 MHz, which allowed us to independently monitor the pD dependence and coupling constants of the H-2 protons. The results obtained indicate that there is little effect of the carboxyl charge on the conformational state(s) of L-carnitine about the C-2/C-3 bond. The NMR data obtained in this study do not support previous solution studies of the pH-dependent conformational changes for DL-carnitine nor the proposed conformation of O-acetyl-DL-carnitine in the crystalline state. |
| Links | |
| Keywords |
Acetylcarnitine; Carnitine/analogs & derivatives; Deuterium; Hydrogen; Magnetic Resonance Spectroscopy/methods; Molecular Conformation; Stereoisomerism |
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