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Updated: May 28, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Amino acid building blocks for efficient Fmoc solid-phase synthesis of peptides adenylylated at serine or threonine
Michael F Albers1, Bart van Vliet, Christian Hedberg
1Department of Chemical Biology, Max-Planck Institute of Molecular Physiology, Otto-Hahn Strasse 11, D-44227, Dortmund, Germany.
Abstract:
The first straightforward building block based (non-interassembly) synthesis of peptides containing adenylylated serine and threonine residues is described. Key features include final global acidolytic protective group removal as well as full compatibility with standard Fmoc solid-phase peptide synthesis (SPPS). The described Thr-AMP SPPS-building block has been employed in the synthesis of the Thr-adenylylated sequence of human GTPase CDC42 (Ac-SEYVP-T(AMP)-VFDNYGC-NH(2)). Further, we demonstrate proof-of-concept for the synthesis of an Ser-adenylylated peptide (Ac-GSGA-S(AMP)-AGSGC-NH(2)) from the corresponding adenylylated serine building block.
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