Ester Dihydrochloride Research Articles

Synthesis of Octopine (Pectenine)

The compound isolated by Moore and Wilson1 from Pecten muscle and called pectenine by them is probably identical with octopine previously isolated by Morizawa.2 The arguments in favor of this statement will be given in a forthcoming publication.Octopine was characterized by Moore and Wilson and, on evidence which was not quite complete, they concluded that the compound is probably arginine, the α-amino group of which is attached to the α-carbon atom of propionic acid. In order to confirm this conclusion a synthesis has been carried out as follows3: d-arginine methyl ester dihydrochloride was treated with the ethyl ester of d-1, α-bromopropionic acid in absolute ethyl alcohol containing a little zinc dust and potassium iodide. Two equivalents of sodium ethylate were added at once and another equivalent added during the early part of the period of boiling which was continued for 24 hours. The esters were hydrolyzed with acid and the material was precipitated by silver and baryta. After decomposing the preci...