Side reactions in the SPPS of Cys-containing peptides |
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Authors: | Panagiotis Stathopoulos Serafim Papas Charalambos Pappas Vassilios Mousis Nisar Sayyad Vassiliki Theodorou Andreas G Tzakos Vassilios Tsikaris |
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Institution: | 1. Department of Chemistry, Section of Organic Chemistry and Biochemistry, University of Ioannina, 45110, Ioanina, Greece
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Abstract: | Alkylation of sensitive amino acids during synthesis of biologically important peptides is a common and well-documented problem in Fmoc-based strategy. Herein, we probed for the first time an unexpected S-alkylation of Cys-containing peptides that occur during the final TFA cleavage of peptides from the Wang solid support. Through a battery of approaches (NMR, UV and LC–MS) the formed by-product was assigned as the alkylation of the cysteine sulfydryl group by the p-hydroxyl benzyl group derived from the acidic Wang linker decomposition. Factors affecting this side reaction were monitored and a protocol that minimizes the presence of the by-product is reported. |
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