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Issue 2, 2016
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Photochemically re-bridging disulfide bonds and the discovery of a thiomaleimide mediated photodecarboxylation of C-terminal cysteines

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Abstract

Described in this work is a novel method for photochemically manipulating peptides and proteins via the installation of cysteine-selective photoactive tags. Thiomaleimides, generated simply by the addition of bromomaleimides to reduced disulfide bonds, undergo [2 + 2] photocycloadditions to reconnect the crosslink between the two cysteine residues. This methodology is demonstrated to enable photoactivation of a peptide by macrocyclisation, and reconnection of the heavy and light chains in an antibody fragment to form thiol stable conjugates. Finally we report on an intriguing thiomaleimide mediated photochemical decarboxylation of C-terminal cysteines, discovered during this study.

Graphical abstract: Photochemically re-bridging disulfide bonds and the discovery of a thiomaleimide mediated photodecarboxylation of C-terminal cysteines

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Publication details

The article was received on 13 Oct 2015, accepted on 16 Nov 2015 and first published on 25 Nov 2015


Article type: Communication
DOI: 10.1039/C5OB02120K
Citation: Org. Biomol. Chem., 2016,14, 455-459
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    Photochemically re-bridging disulfide bonds and the discovery of a thiomaleimide mediated photodecarboxylation of C-terminal cysteines

    D. A. Richards, S. A. Fletcher, M. Nobles, H. Kossen, L. Tedaldi, V. Chudasama, A. Tinker and J. R. Baker, Org. Biomol. Chem., 2016, 14, 455
    DOI: 10.1039/C5OB02120K

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