Synthesis, characterization, and evaluation of PS-PPDC resin: a novel flexible cross-linked polymeric support for solid-phase organic synthesis.
The present study describes the synthesis of different mole densities of poly(propylene glycol)dimethacrylate cross-linked resins using monomer units such as styrene and 4-chloromethyl styrene and its evaluation as an ideal support toward different stages of solid-phase peptide synthesis. Free radical generated aqueous suspension polymerization has been followed for polymerization and the formation of resin was characterized using infrared and carbon-13 spectroscopic techniques. Surface morphology of resin was examined by scanning electron microscopy. The polymerization reaction was investigated with respect to the effect of amount of cross-linking agent to verify the swelling, loading, and the mechanical stability of resin. Solvent imbibition abilities in commonly used solvents were measured and compared to commercially available Merrifield as well as reported styrene-acryloyloxyhydroxypropyl methacrylate-tripropyleneglycol diacrylate (SAT resins. The chemical inertness of the support was also checked with different reagents used for solid-phase peptide synthesis. The suitability of support was demonstrated by synthesizing biologically potent Endothelin class of linear peptides by Fmoc strategy and compared to SAT resin. The purities of synthetic peptides were analyzed by high-performance liquid chromatography and corresponding masses by matrix-assisted laser desorption/ionisation-time of flight analysis.
Chemical Biology, Molecular Medicine Division, Rajiv Gandhi Centre for Biotechnology, Poojappura, Thiruvananthapuram, Kerala 695 014, India.
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Siyad
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Vinod Kumar
D002851:Chromatography, High Pressure Liquid; D009682:Magnetic Resonance Spectroscopy; D008855:Microscopy, Electron, Scanning; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques; D017550:Spectroscopy, Fourier Transform Infrared
D011108:Polymers