DOPA, synthesis

A Garzon, A Poupaert, M Claesen, P Dumont. A lymphotropic prodrug of L-dopa Synthesis, pharmacological properties, and pharmacokinetic behavior of 1,3-dihex-adecanoyl-2-r(S)-2-amino-3-(3,4-dihydroxyphenyl) propanoyl] propane-1,2,3-triol. J Med Chem 29 687-691, 1986. 

R. Chirakal, N. Vasdev, G.J. Schrobilgen, C. Nahmias, Radiochemical and NMR spectroscopic investigation of the solvent effect on the electrophilic elemental fluori-nation of l-DOPA Synthesis of [F-18]5-fluoro-L-DOPA, J. Fluor. Chem. 99 (1999) 87-94. 

Ischiropoulos, H., Duran, D., and Horwitz, J., Peroxynitrite-mediated inhibition of DOPA synthesis in PC12 cells. J. Neurochem. 65, 2366-2372 (1995). 

Seitz G, Gebhardt S, Beck JF, Bohm W, Lode HN, Niethammer D, and Bruchelt G (1998) Ascorbic acid stimulates DOPA synthesis and tyrosine hydroxylase gene expression in the human neuroblastoma cell line SK-N-SH. Neuroscience Letters 244,33-6. 

Compound NR,R2 pHJSpiperone Binding (IC50/ nM) Inhibition of Mouse Locomotor Activity ED50 mg/kgip % Reversal of Striatal DOPA Synthesis After GBL... 

We have shown that L-tyrosine and the related amino acids can be synthesized in high yields through the reverse of a, 3-elimination. In the case of L-dopa synthesis by the resting cells of E. herbicola, more than lOOg of L-dopa was synthesized in 1 liter of reaction mixture with a significantly high yield for the substrates, pyruvate and pyrocatechol. Based on these results, Ajinomoto Co. Ltd. started the commercial production of L-dopa in 1994. 

DePietro FR, Fernstrom JD. The relative roles of phenylalanine and tyrosine as substrates for DOPA synthesis in PC12 cells. Brain Res 1999 831 72-84. 

Munoz AJ et al (2011) Metabolic engineering of Escherichia coli for improving L-3,4-dUiydroxyphenylalanine (L-DOPA) synthesis from glucose. J Ind Microbiol Biotechnol 38 1845-1852... 

Speculation still surrounds some of the aromatic hydroxylation processes which are believed to operate in higher plants. Griffith and Conn have thus shown, contrary perhaps to expectation, that partially purified phenolase preparation from Vicia faba do not catalyse the conversion of L-tyrosine to L-dopa and they concluded that phenolase does not appear to play a role in L-dopa synthesis. 

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