Synthesis and characterization of N,N-dichlorinated amino acids: Taurine, homotaurine, GABA and L-leucine

Epilepsy, trauma and other circumstances leading to hyperexcitable conditio ns in the CNS tend neurochemically to be associated with excessive stimulat ed release of glutamic acid and/or a failure of GABA modulated inhibition. Somewhat to a lesser extent, taurine and its homologue homotaurine. have al so been shown to antagonize the excitatory actions of glutamic acid. Here w e report the successful synthesis and isolation in pure form of N,N-dichlor inated GABA, taurine, homotaurine and leucine. These compounds are much mor e lipophilic than their parent compounds and may therefore more readily pen etrate the blood-brain barrier systems into the neural tissue, where they c an be easily dechlorinated. Very preliminary biological testing shows that this may indeed occur. The synthesis and purification methodology will like ly also be applicable to a number of other amino acids as well as certain p eptides or selected proteins.