Acylcarnitine profiles have been used as a biomarker for the clinical diagnoses of metabolic disorder diseases, such as medium and long-chain acyl- CoAdehydrogenase (MCAD, LCAD) deficiency by using tandem mass spectrometry analyses. Acyltransferace enzymes reversibly interconvert acyl-COA and acylcarnitine derivatives, thereby it catalyze the translocation of the fatty acyl moiety across the mitochondrial membrane. Current invistigations found that acylcarnitine induced oxidative stress, and insulin resistance have been reversed by applying antioxidants treatment , and concluded that incomplete fatty acid β-oxidation in muscle tissues result in accumulation and increase in acyl carnitine levels in different skeletal muscle tissues. We present a developed method for the synthesis of less common medium chains acyl carnitines stereoisomers that formed during gut microbe metabolism. We synthesized cis-3,4-methylene-heptanoylcarnitine and its stereoisomer trans-3,4-methylene-heptanoylcarnitine, the synthesis will be presented, based on O-Acylation of carnitine chloride, and replacement of the acid chloride by thionyl chloride followed by the addition of carnitine chloride. Furthermore the spectroscopic characterization of the free fatty acids and the two acylcarnitine steroisimers will be achieved using 400 MHz NMR, GC/MS EI-QQQ, and LC/MS QTRAP 5500. Both synthesized steroiomers will be purified by solid phase extraction –SPE-, followed by high performance liquid chromatography-HPLC. Additionally we identified cis -3,4-methylene-heptanoylcarnitine, and its trans isomer in plasma and skeletal muscle tissue by liquid chromatography-mass spectrometry analyses.

Synthesis, spectroscopic characterization & detection of cyclopropyl heptanoylcarnitine stereoisomers in human plasma

ACS Spring 2022

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