SPED-(Styrene-Polyethyleneglycol Diacrylate-9-Decen-1-ol) - A Novel Resin for Solid Phase Peptide Synthesis; Synthesis and Characterization of Biologically Potent Endothelin Classes of Peptides

Mohammedhaneefa      A. Siyad; Gopalakrishnapillai      S.V. Kumar

doi:10.2174/138620712800194512

Abstract

Here we present a novel beaded chemically stable, highly permeable hydrophobic/hydrophilic balanced support for solid phase peptide synthesis. The resin (SPED) was prepared by free radical suspension polymerization using monomers styrene and 9-decen-1-ol with amphiphilic cross-linking agent polyethyleneglycol diacrylate (Mn≈ 258). Different cross-linking densities were prepared to check the extent of swelling in different polar and non-polar solvents. The SPED resin was characterized with IR, 13C NMR and surface by SEM. The chemical stability of the support in various peptide synthetic conditions was investigated and monitored by IR spectroscopy. To evaluate the applicability of the new resin in synthetic conditions more challenging peptide sequence of retro-ACP (74-65) was synthesized and compared to commercially available Merrifield resin. The efficiency of SPED was further confirmed by synthesizing biologically important endothelin family of peptides in high yield and purity. The purity of all peptides was checked by RP-HPLC and mass by MALDI-TOF MS.

Keywords: Endothelin, peptide, resin, solid phase peptide synthesis

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