Peptide syntheses with the 2,4,6-trimethylbenzyl esters of L-asparagine and L-glutamine

Abstract

The 2,4,6-trimethylbenzyl esters of L-asparagine and L-glutamine have been obtained as the crystalline hydrochlorides by treatment of the o- nitrophenylsulphenyl amino acid esters with methanolic hydrogen chloride. These hydrochlorides were used in the synthesis of several benzyloxycarbonyl peptide 2,4,6-trimethylbenzyl esters, which were converted into the corresponding free peptides by the action of hydrogen bromide in acetic acid under mild conditions.