SYNTHÈSES DE DÉRIVÉS DE LA LYSINE

Abstract

New N-ε-substituted lysines have been synthetized as follows: by condensing 5-δ-bromobutylhydantoin with different primary amines, 5-δ-alkylaminobutylhydantoins were obtained, the alkaline hydrolysis of which gave the corresponding N-ε-substituted lysines. N-α-Substituted hexahomoserines have also been prepared by acid hydrolysis of the reaction product between α,ε-dihydroxycaproic nitrile and primary amines. 5-Amino-5-carboxypentane sulphonamide has been prepared in the following way: 5-δ-bromobutylhydantoin was reacted with thiourea, and the resulting isothiouronium salt was oxidized with chlorine. Gaseous ammonia was then bubbled through an ethereal suspension of the 5-δ-chlorosulphonyl butylhydantoin and the resulting sulphonamide was hydrolyzed under pressure with barium hydroxide. 5-Amino-5-carboxypentane sulphonamide was then isolated and crystallized.