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Four optically-active dipeptides of L-histidine containing di-(2-chloroethyl)amino groups have been synthesized: the methyl esters of p-di-(2-chloroethyl)aminophenylacetyl-L-histidyl-L-leucine, of p-di-(2-chloroethyl)aminophenylacetyl-L-leucyl-L-histidine, of p-di-(2-chloroethyl)aminophenylacetyl-L-histidyl-L-histidine, and of p-di-(2-chloroethyl)aminophenylacetyl-L-histidyl-L-methionine.
The methyl esters of the dipeptide p-di-(2-chloroethyl)aminophenylacetyl-L-histidyl-L-leucine synthesized by the azide method and by the p-nitrophenyl ester method had the same angles of optical rotation as the same dipeptide obtained by using the 1,3-dicyclohexylcarbodiimide method alone.
The condensations of p-di-(2-chloroethyl)aminophenylacetyl-L-histidine with the methyl esters of L-leucine, L-histidine, and L-methionine with the aid of 1,3-dicyclohexylcarbodiimide were carried out in dimethyl sulfoxide with no protection of the imidazole ring of the histidine.
KeywordsPeptide Ester Methyl Ester Dimethyl Imidazole
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