An Improvement for the Synthesis of a Styrene-Divinylbenzene, Copolymer Based, 6-Aminoquinoline Carbamate Reagent. Applications for Derivatlzation of Amino Acids, Peptides, and Proteins

Abstract

Abstract An improved method for the synthesis of a styrene-divinylbenzene based 6-aminoquinoline carbamate (6-AQC) reagent with a benzotriazole linkage is reported in this paper. By using 6-arninoquinoline (6-AQ) and triphosgene as the starting materials, the synthesis of the intermediate quinoline-64socyanate became much simpler. Directly from quinolyl-6-isocyanate, instead of from the rearrangement of quinolyl acyl azide, a polymeric reagent with high loading and few adsorbed impurities was obtained. This was then used for the derivatization of amino acids (AAs) and peptides. High efficiencies and reproducibilities of the derivatizations make this reagent attractive for the analysis of AAs and small peptides. The reagent was also used for a derivatization study of proteins. This was the first time that any polymeric reagent has been described for the successful, more selective tagging of larger proteins. The effect of surfactants on the reaction was also studied. Derivatizations with the solid polymeric...