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

We have developed a new cross-linked polymeric support by the copolymerizat ion of styrene and butanediol dimethacrylate (BDODMA) for the solid-phase s ynthesis of peptides. The resin support was synthesized in various cross-li nking densities by radical aqueous suspension polymerization. The copolymer was characterized by IR and C-13 NMR techniques. The shape, size, and morp hological features of the cross-linked polymer bead were analyzed by scanni ng electron microscopy. PS-BDODMA polymer support showed excellent swelling properties in all types of solvents that are used in solid-phase peptide s ynthesis (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 e ven after 48 h treatment with TFA, 20% piperidine in DMF, aqueous NaOH, hyd roxylamine in aqueous MeOH, and Liquor ammonia. The resin can be functional ized with chloromethyl, aminomethyl, and hydroxymethyl groups under various reaction conditions. The efficiency of this new support was demonstrated b y the synthesis of few model peptides with very high purity and yield. Thes e peptides were characterized by MALDI TOF MS and amino acid analysis.