A rapid and efficient method for the synthesis of selectively S-Trt or S-Mmt protected Cys-containing peptides

作者：Stathopoulos Panagiotis; Papas Serafim; Sakka Marianna; Tzakos Andreas G; Tsikaris Vassilios^*

来源：Amino Acids, 2014, 46(5): 1367-1376.

DOI：10.1007/s00726-014-1696-0

• Solid phase peptide synthesis
• Cysteine
• S-Trt
• S-Mmt
• TFA cleavage

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.

• 出版日期2014-5