Tetraethyleneglycol diacrylate (TTEGDA)-crosslinked polystyrene resin as an efficient solid support for gel phase peptide synthesis

Abstract

Various applications of the newly developed tetraethyleneglycol diacrylate (TTEGDA)-crosslinked polystyrene resin are illustrated by the synthesis of model peptides, fully protected peptides, peptide amides and biologically important sequences. PS-TTEGDA resin was prepared by suspension polymerization of styrene and TTEGDA and functionalized with chloromethyl, 4-cholromethyl-3-nitro, aminomethyl, α-bromopropionyl, α-aminopropionyl, 4-bromomethyl 3-nitrobenzamido, 4-aminomethyl-3-nitrobenzamido groups. Peptide synthesis was carried out using these modified resins by standard solid phase methodology. Coupling and deprotection in this synthetic strategy went to near completion showing the positive role of hydrophilic and flexible crosslinking agent TTEGDA in facilitating gelphase reactions. The peptides were removed from the support by photolysis, trifluoroaceticacid (TFA) treatment,trans-esterification or ammonolysis in high purity and yield. The crude peptides were purified by column chromatography/FPLC and characterized by aminoacid analysis, sequencing or ¹H-NMR.