SYNTHESIS AND HYDROXYLAMINOLYSIS OF N-CARBOXYMETHYL-N-ACETYL-L-GLUTAMIC ACID DIMETHYLESTER

N-carboxymethyl-N-acetyl-l-glutamic acid dimethylester (CM-AGAdiME) has been synthesized from acetyl-l-glutamic acid dimethylester and methyl chlorofor-mate. The synthesis of this compound was undertaken to allow us to ascertain if N-carboxy-N-acetyl-l-glutamate was formed as an intermediate in the reaction catalyzed by the ureotelic liver carbamyl phosphate synthetase. The latter substance was not detected in the enzyme reaction. When the diacylamine, CM-AGAdiME, is subject to hydroxylaminolysis at pH 6 or 14, acethydroxamate is formed as rapidly as with other acyl anhydrides; a result in keeping with the anhydride character of diacylamines. In an attempt to isolate N-acetyl-N-carboxyglutamic acid from CM-AGAdiME, the ester was subjected to liver aliesterase which removed quantitatively only one methyl group from the γ-carboxyl of CM-AGAdiME. The rapid decomposition of carboxymethylhydroxamate in acidic ferric chloride solutions is also described. © 1969.