The concept of internal solubilization in peptide synthesis: ethylene glycol-based protecting groups

L. Kocsis, T. Bruckdorfer, G. Orosz

Tetrahedron Lett. 2008; 49: 7015-7017; https://doi.org/10.1016/j.tetlet.2008.09.126

Abstract: A novel, ethylene glycol-based protecting group is designed and synthesized for use in solid phase peptide synthesis. Ether and ester type protected amino acids are prepared. The acid stability of the new protecting group showed complete Fmoc/t-Bu compatibility. The new derivatives are tested in solid phase peptide synthesis, with a ‘difficult’ sequence to examine the disruption of peptide aggregation.Graphical abstractAn Fmoc compatible side chain protecting group family is developed, which inhibits peptide chain aggregation. Protected amino acid derivatives can easily be incorporated into existing automated and manual peptide synthesis protocols.