Tri(propylene glycol) glycerolate diacrylate cross-linked polystyrene: a new resin support for solid-phase peptide synthesis.
A highly flexible, mechanically and chemically stable copolymer, tri(propylene glycol) glycerolate diacrylate cross-linked polystyrene (PS-TRPGGDA), was synthesized by the suspension polymerization and employed as a solid support for peptide synthesis. The beaded polymer support containing secondary hydroxyl functional groups in the cross-linker was used as the growth site for peptide synthesis. The procedure is unique and cost-effective in that it avoids the initial functionalization steps required for most of the styrene-based polymer supports. The resin was characterized by 13C-CP-MAS NMR spectroscopy and the morphologic features of the resin were investigated using scanning electron microscopy. Swelling studies conducted on the new support revealed that the PS-TRPGGDA resin undergoes more effective swelling and solvation than PS-DVB resin in all solvents used in peptide synthesis. The efficiency of the new support was demonstrated by synthesizing a 'difficult' sequence Ala-Arg-(Ala)6-Lys and comparing it with commercially available Merrifield and Sheppard resins. The synthetic efficiency was further demonstrated by the synthesis of a 24-residue NR 2A peptide substrate of calcium/calmodulin-binding peptide. The high yield and purity of the peptide synthesized on the novel support indicates the positive role of the flexible and hydrophilic cross-linking agent in the solid support.
Sasikumar
P G
PG
School of Chemical Sciences, Mahatma Gandhi University, Kottayam 686560, Kerala, India.
Kumar
K S
KS
Rajasekharan Pillai
V N
VN
D000179:Acrylates / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D003432:Cross-Linking Reagents; D005990:Glycerol / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008855:Microscopy, Electron, Scanning; D009842:Oligopeptides / Q000138:chemical synthesis; D010452:Peptide Biosynthesis; D011137:Polystyrenes / Q000138:chemical synthesis*; D019946:Propylene Glycol / Q000737:chemistry; D012117:Resins, Synthetic / Q000138:chemical synthesis*; D012997:Solvents; D017550:Spectroscopy, Fourier Transform Infrared
D000179:Acrylates; D003432:Cross-Linking Reagents; D009842:Oligopeptides; D011137:Polystyrenes; D012117:Resins, Synthetic; D012997:Solvents; C106660:alanyl-arginyl-(alanyl)(6)-lysine; D019946:Propylene Glycol; D005990:Glycerol