Influence of amino acid and N-terminal protection residue structures on peptide p-nitroanilide adsorption on polystyrene-based support

Abstract

Abstract Polystyrene-based granulated support Bio-Beads® SM-2 was employed for the separation of peptide-p-nitroanilides from Na2SO4 and Na2SO5 mixture (Oxone®) after oxidation of peptide-p-aminoanilides. Unsubstituted phenyl-containing N-terminal protection groups (such as carbobenzoxy or tested earlier benzoyl) and Phe residues ensured an efficient adsorption of peptide-p-nitroanilides onto Bio-Beads® SM-2. Neither such aromatic groups as tosyl, 9-fluorenyl(methoxycarbonyl), p-nitroanilide nor indolyl or p-hydroxyphenyl groups of Trp and Tyr residues provide peptide-p-nitroanilides with the ability to adsorb onto the polystyrene-based support. Hence, peptides and their derivatives should contain at least one unsubstituted phenyl group to ensure an efficient separation and purification via adsorption chromatography on Bio-Beads® SM-2. This chromatographic support is well suitable for desalting or separation of phenyl group-containing peptides, especially in multiple parallel preparation and high-throughput screening experiments.