1-(α-Diazobenzyl)pyrene: A Reagent for Photolabile and Fluorescent Protection of Carboxyl Groups of Amino Acids and Peptides

Abstract

1-(α-Diazobenzyl)pyrene (1c), red prisms stable at room temperature for more than three months, reacted with the p-toluenesulfonic acid salts of amino acids to give the corresponding highly fluorescent amino acid α-(1-pyrenyl)benzyl ester salts in moderate yield. The amino acids were recovered by irradiation at 340 nm in methanol. Application of this method to dipeptides is also described.