Synthesis, characterization, and application of butanediol dimethacrylate cross-linked polystyrene: a flexible support for gel phase peptide synthesis

Abstract

We have developed a new cross-linked polymeric support by the copolymerization of styrene and butanediol dimethacrylate (BDODMA) for the solid-phase synthesis of peptides. The resin support was synthesized in various cross-linking densities by radical aqueous suspension polymerization. The copolymer was characterized by IR and ¹³C NMR techniques. The shape, size, and morphological features of the cross-linked polymer bead were analyzed by scanning electron microscopy. PS-BDODMA polymer support showed excellent swelling properties in all types of solvents that are used in solid-phase peptide synthesis (SPPS). The stability of polymer in various reagents and solvents was tested by IR. The polymer does not show any change in its IR spectrum even after 48 h treatment with TFA, 20% piperidine in DMF, aqueous NaOH, hydroxylamine in aqueous MeOH, and liquor ammonia. The resin can be functionalized with chloromethyl, aminomethyl, and hydroxymethyl groups under various reaction conditions. The efficiency of this new support was demonstrated by the synthesis of few model peptides with very high purity and yield. These peptides were characterized by MALDI TOF MS and amino acid analysis.