Comparative acidic cleavage experiments with methyl-substituted benzyl esters of amino acids

Abstract

The action of trifluoroacetic acid and hydrogen bromide in acetic acid, respectively, on the benzyl, p-methylbenzyl, 2,4,6-trimethylbenzyl, and penta-methylbenzyl esters of some amino acid derivatives has been investigated by thin-layer chromatography. Methyl substitution greatly enhances the lability of the ester groups. The possible bearing of the results on solid-phase peptide synthesis is discussed.