SYNTHESIS, CHARACTERIZATION AND APPLICATION OF TETRAETHYLENE GLYCOL DIACRYLATE CROSS-LINKED POLYSTYRENE SUPPORT FOR GEL PHASE PEPTIDE-SYNTHESIS

Styrene and tetraethylene glycol diacrylate (TTEGDA) were copolymerize d by the free radical aqueous suspension polymerization technique, emp loying toluene as the monomer diluent at 80 degrees C. The resulting b eads were functionalized by chloromethylation. The co-polymer was char acterized by IR and high-resolution solid-state C-13-NMR techniques. S canning electron microscopy was employed to observe shape, size, and m orphological features of the crosslinked bead copolymer. The swelling capacities of the copolymer were measured in various solvents. Reactiv ity of the amino functionalized polymer was compared with divinylbenze ne-polystyrene (I'S) resin. Stability of the copolymer was tested unde r various peptide synthetic conditions. High capacity chloromethyl TTE GDA-crosslinked PS was employed as a solid support in the synthesis of the hydrophobic peptide Boc(Ala-Leu-Ala)(4)-OMe. The coupling and dep rotection steps in the synthetic scheme proceeded in near quantitative yields, supporting the positive role of the flexible and hydrophilic crosslinking agent. The fully protected 12-residue peptide was cleaved from the support by a transesterification procedure in 85% overall yi eld and characterized by thin-layer chromatography, amino acid analysi s, and H-1-NMR. (C) 1996 John Wiley & Sons, Inc.