Optimization of butanediol dimethacrylate crosslinked polystyrene: A novel polymeric support for solid phase peptide synthesis |
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Authors: | Ajikumar P K Devaky K S |
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Institution: | (1) School of Chemical Sciences, Mahatma Gandhi University, Priyadarsini Hills, 686 560 Kottayam, Kerala, India |
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Abstract: | Summary Studies leading to optimization of butanediol dimethacrylate-crosslinked polystyrene supports (BDDMA-PS) for solid phase peptide
synthesis are delineated. BDDMA-PS copolymers with different crosslink densities were prepared and functionalised with chloromethyl
groups. The reactivity of the Lys(2-Cl−Z)−OH residue bound to these polymers through a benzyl ester linkage was investigated
by following the kinetics of acylation by the HOBt active ester of Boc-Alanine. From the results it was observed that the
rate of peptide bond formation was maximum for a 2% BDDMA crosslinked resin. This resin was compared with a 2% DVB-crosslinked
polystyrene resin (DVB-PS). Synthesis of an extremely insoluble, hydrophobic, antiparallel β-sheeted difficult sequence peptide
LMVGGVVIA (β 34–42), C-terminal fragment of β-amyloid protein, β (1–42), was carried out on both 2% DVB-PS and 2% BDDMA-crosslinked
polystyrene supports. The synthesis of the peptide was carried out using Boc amino acid strategy. Greater extent of swelling
of the resino peptide, increased coupling efficiency during the assembly of amino acids and relatively high purity of synthesised
peptide were observed in the case of 2% BDDMA-PS polymer. |
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Keywords: | butanediol dimethacrylate crosslinked polystyrene solid phase peptide synthesis |
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