Application of microwave method to the solid phase synthesis of pseudopeptides containing ester bond |
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Authors: | Bishnu Prasad Joshi |
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Institution: | Department of Chemistry, Bio-organic Chemistry Lab, 253-Yunghyun-Dong, Nam-Gu, Incheon, 402-751, South Korea |
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Abstract: | A new procedure was developed for reducing the reaction time and improving the yield of esterification reaction in solid phase synthesis of pseudopeptides containing an ester bond by utilizing microwave irradiation. We selected a pseudodipeptide (Fmoc-LysΨCOO]Leu-NH2) and optimized the microwave-assisted esterification reaction in solid phase synthesis using Fmoc chemistry. For this, microwave-assisted esterification reactions with different reaction time, temperature, and solvents were performed using 1,3-diisopropylcarbodiimide (DIC) as the coupling reagent. We synthesized several pseudodipeptides containing an ester bond by using the optimized microwave irradiation method. The purity and yield of the pseudodipeptides synthesized in this way were better than those obtained without microwave irradiation. Furthermore, we applied this methodology for synthesizing pseudopeptides (6- and 12-mer) corresponding to the α helical peptide. The microwave-assisted esterification reaction afforded the target pseudopeptides with high yield (∼80%) and purity within 12 min, whereas the reaction without microwave irradiation afforded the target compound with poor yield (∼45%) and low purity. |
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Keywords: | Microwave Irradiation Pseudopeptides Ester bond Solid phase synthesis Peptide |
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