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Updated: Feb 7, 2026

Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
Water-soluble allyl sulfones for dual site-specific labelling of proteins and cyclic peptides
Tao Wang1, Andreas Riegger1, Markus Lamla1
1Institute of Organic Chemistry III , Ulm University , Albert-Einstein-Allee 11 , D-89081 Ulm , Germany .
Abstract:
Water-soluble allyl sulfones provide convenient site-specific disulfide rebridging of native proteins and cyclic peptides. The site-selective functionalization of (a) the peptide hormone somatostatin, (b) the interchain disulfide of bovine insulin and (c) functionalization of the proteins GFP and lysozyme with allyl sulfones proceeds in aqueous solution. Allyl sulfones offer three functionalizable sites that react with thiol containing molecules in a step-wise fashion. Dual labeling of proteins and cyclic peptides is achieved i.e. the attachment of a chromophore and an affinity tag in a single reaction step, which is of great significance for the construction of precise multifunctional peptide and protein conjugates.
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