1440539-10-5Relevant academic research and scientific papers
Side reactions in the SPPS of Cys-containing peptides
Stathopoulos, Panagiotis,Papas, Serafim,Pappas, Charalambos,Mousis, Vassilios,Sayyad, Nisar,Theodorou, Vassiliki,Tzakos, Andreas G.,Tsikaris, Vassilios
, p. 1357 - 1363 (2013/06/27)
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.
