Synthesis of gamma-glutamyldopamine and other peptidoamines in the nervous system of Aplysia californica.

The synthesis of a series of gamma-glutamyl amines (gamma-Glu-amines), including gamma-Glu-dopamine, gamma-Glu-5-hydroxytryptamine, gamma-Glu-octopamine, gamma-Glu-tryptamine, gamma-Glu-tyramine, and gamma-Glu-phenylethylamine, by nervous tissue of the marine mollusc Aplysia californica is described. After ganglia were incubated in vitro with 14C-amines, the unchanged amine and a new 14C-labeled product, identified as the gamma-Glu conjugate of the amine, were isolated from the tissue extracts. Identification was made by comparing the chromatographic properties (HPLC, TLC, and LC) of the isolated conjugates with chemically synthesized gamma-Glu-amines before and after acid hydrolysis.