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L- carnitine as a powerful natural bioactive substance is known to protect the functional cells and to promote the production of energy in cells. L-carnitine is a essential amino acid that play an important role as a cofactor in ATP production in the mitochondrial matrix. L-carnitine has proved to be very useful for the treatment of obesity, inflammatory, heart failure and nervous system disorders and so on. Therefore, the synthesis of L-carnitine and its derivatives and the applications as aging inhibitors of cells have been widely studied.
Many previous researchers had first synthesized (S)-3, 4-dihydroxybutyric acid from maltose and then (S)-3-hydroxy-γ-butyrolactone by methylation and lactonization to obtain L-carnitine.
We have synthesized directly (S)-3-hydroxy-γ-butyrolactone from oligosaccharide and then L-carnitine.
The synthesis of L-carnitine was studied by three reaction steps; at the first step, (S)-3-hydroxy-γ-butyrolactone was synthesized by the treatment of oligosaccharide with hydrogen peroxide and by the continued lactonization in the strong acid medium. At the second step, (S)-3-methanesulfonyloxy-γ-butyrolactone was synthesized by the mesylation and at the third step L-carnitine was synthesized by treatment with trimethylamine.
We measured its melting point, optical rotation, IR spectrum, 1H-NMR spectrum, mass spectrum for the identification of its structure and its purity was determined by using Ultrahigh-speed liquid chromatography(UPLC).
In future, we are going to study synthetic methods of L-carnitine derivatives with better cell membrane permeability and more effective behaviors for the protection of mitochondrial functions than L-carnitine.
