Compounds Related to Canaline and Canavanine

In 1929 Kitagawa (l-3) and his collaborators isolated from the non-protein fraction of jack bean (Cunavaliu ensiformis) an amino acid, canavanine, which is decomposed by an enzyme present in liver into urea and another amino acid, canaline.He assigned the following form&e to the two compounds.C-N-0-CHP--CH2-C-COOH -+ / NH Canavanine H (NH*)&0 + HPN-0-CH2-CH2--C-COOH I NH, Canaline These structures were confirmed by means of degradation experiments by Gulland and Morris (4).The discovery of a naturally occurring ether of hydroxyguanidine makes desirable further knowledge of the general properties of this type of compound, and of the related ethers of hydroxylamine, which have received relatively little attention.Experiments have therefore been undertaken to develop convenient