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. 2025 Feb 7;27(5):1159-1163.
doi: 10.1021/acs.orglett.4c04671. Epub 2025 Jan 23.

Shining a Light on Peptide and Protein Synthesis: Light-Emitting-Diode-Driven Desulfurization of Cysteine to Alanine with Rose Bengal

Mateusz Waliczek  1 , Piotr Stefanowicz  1
Affiliations

Shining a Light on Peptide and Protein Synthesis: Light-Emitting-Diode-Driven Desulfurization of Cysteine to Alanine with Rose Bengal

Mateusz Waliczek et al. Org Lett. .

Abstract

Studies presenting visible-light-induced desulfurization of peptides containing a cysteine residue have been carried out. This transformation driven by light-emitting-diode-type light proceeds with high efficiency in an aqueous solution at room temperature and involves the use of a catalytic amount of photosensitizer, Rose Bengal. The procedure has been tested on model synthetic peptides, lysozyme C and α-crystallin, and successfully applied to a one-pot native chemical ligation (NCL)-desulfurization protocol.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Diagram of examples of cysteine desulfurization methods.
Figure 2
Figure 2
Scheme of visible-light-induced desulfurization of model peptide H-Thr-Gly-Cys-Ala-Phe-Lys-NH2. LC–MS [extracted ion chromatogram (XIC)] chromatogram obtained for the mixture after desulfurization and the electrospray ionization mass spectrometry (ESI–MS) spectrum of the reaction product.
Figure 3
Figure 3
(A) Schematic representation of one-pot NCL–desulfurization, (B) ESI–MS spectrum of the reaction product, and (C) LC–MS (XIC) chromatogram obtained for the mixture after the desulfurization protocol.
Figure 4
Figure 4
Schematic representation of protein desulfurization, sequence coverage of α-crystallin tryptic digest with desulfurized cysteine residue highlighted, sequence coverage of lysozyme C tryptic digest with desulfurized cysteine residues highlighted, and table showing the percentage efficiency of desulfurization of lysozyme C depending upon the position in the sequence.
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