Abstract
Selective removal of protecting groups under different cleavage mechanisms could be an asset in peptide synthesis, since it provides the feasibility to incorporate different functional groups in similar reactive centres. However, selective protection/deprotection of orthogonal protecting groups in peptides is still challenging, especially for Cys-containing peptides, where protection of the cysteine side-chain is mandatory since the nucleophilic thiol can be otherwise alkylated, acylated or oxidized. Herein, we established a protocol for the synthesis of Cys-selective S-Trt or S-Mmt protected Cys-containing peptides, in a rapid way. This was achieved by, simply fine-tuning the carbocation scavenger in the final acidolytic release of the peptide from the solid support in the classic SPPS.
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Acknowledgments
The article is in line of a research project, co-financed by the European Union (European Regional Development Fund—ERDF) and Greek national funds through the Operational Program “Competitiveness and Entrepreneurship” of the National Strategic Reference Framework (NSRF)—Research Funding Program: Synergasia 2009. Action I. Cooperative small- and mid-scale projects (Project code: 09SYN-12-827). This research has been co-financed by the European Union (European Social Fund—ESF) and Greek national funds through the Operational Program “Education and Lifelong Learning” of the National Strategic Reference Framework (NSRF)—Research Funding Program: THALES Investing in knowledge society through the European Social Fund. (Acronym: FeRedox; ID: 1356). Moreover, special thanks are given to the Mass Spectrometry Unit of University of Ioannina, for providing access to the LC-MS/MS facilities.
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Stathopoulos, P., Papas, S., Sakka, M. et al. A rapid and efficient method for the synthesis of selectively S-Trt or S-Mmt protected Cys-containing peptides. Amino Acids 46, 1367–1376 (2014). https://doi.org/10.1007/s00726-014-1696-0
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DOI: https://doi.org/10.1007/s00726-014-1696-0