Synthesis of cyclo-PLAI using a combination of solid- and solution-phase methods |
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Authors: | Orin Inggriani Napitupulu Dadan Sumiarsa Toto Subroto Nurlelasari Desi Harneti Unang Supratman |
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Institution: | 1. Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Padjadjaran, Jatinangor, West Java, Indonesia;2. Laboratorium Sentral, Universitas Padjadjaran, Jatinangor, West Java, Indonesia |
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Abstract: | Cyclo-PLAI was successfully synthesized using a combination of solid- and solution-phase methods. This current synthesis was found to be faster than the previously reported synthesis for the cyclic peptide. The linear precursor was synthesized on 2-chlorotrityl resin with Fmoc/t-Bu strategy. HATU/HOAt was employed as the coupling reagent in the amide bond formation on the resin. Cyclization of the linear precursor was experimented with HATU/HOAt reagents with different conditions. However, the linear precursor was best cyclized using HATU reagent in DIPEA by stirring the reaction mixture at 0?°C for 1?h and followed by stirring the reaction mixture at room temperature for 30?min, giving the cyclic product in 70% yield (calculated from the linear peptide). Both linear and cyclic products were characterized using HR-TOF-ESMS, 1H-NMR, 13C-NMR, and compared with previously reported spectral data for the cyclic product. |
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Keywords: | Cyclo-PLAI cyclotetrapeptide HATU cyclization solid-phase peptide synthesis 2-chlorotrityl resin |
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