Poly(styrene-co-glycerol dimethacrylate): synthesis, characterization, and application as a resin for gel-phase peptide synthesis

Abstract

An efficient cross-linked polymer support for solid-phase synthesis was prepared by introducing glycerol dimethacrylate cross-linker to polystyrene network using free radical aqueous suspension polymerization. The support was characterized by various spectroscopic methods. Morphological feature of the resin was analyzed by microscopy. The polymerization reaction was investigated with respect to the effect of amount of cross-linking agent, which in turn vary the swelling, loading, and the mechanical stability of the resin. The solvent uptake of the polymer was studied in relation to cross-linking and compared with Merrifield resin. The stability of the resin was tested in different synthetic conditions used for solid-phase peptide synthesis. Hydroxy group of the support was derivatized to chloro and then amino groups using different reagents and reaction conditions. Efficiency of the support was tested and compared with TentaGel™ resin by following different steps involved in the synthesis of the 65–74 fragment of acyl carrier protein. The results showed that the poly(styrene-co-glycerol dimethacrylate) (GDMA-PS) is equally efficient as TentaGel resin in peptide synthesis. The purity of the peptides was analyzed by HPLC and identities were determined by mass spectroscopy and amino acid analysis.