Selective Coupling of Aminophosphole-Based Fluorophores to Unprotected Peptides through P–S Bond Formation
Phosphole-based fluorophores are attractive dyes for bioimaging due to their relatively compact molecular structures, strong fluorescence up to the near-infrared region with large Stokes shifts, and remarkable resistance to photobleaching. Therefore, the development of efficient and chemoselective coupling methods for functionalizing phospholes is of significant interest for biomolecular labeling. Herein, we describe the synthesis of novel P-aminophospholes and their use for direct conjugation to cysteinyl peptides under mild conditions. The utility of this approach was demonstrated by successfully labeling the bioactive peptide ghrelin(1,8)-Cys9, as well as the growth hormone secretagogue receptor, without affecting its biological activity.
Authors
- Laure Liénart (ORCID: https://orcid.org/0009-0004-0495-6541)
- Jean‐Louis Banères (ORCID: https://orcid.org/0000-0001-7078-1285)
- Arie van der Lee (ORCID: https://orcid.org/0000-0002-4567-1831)
- Miyanou Rosales‐Hurtado (ORCID: https://orcid.org/0000-0003-2988-4244)
- Florine Cavelier (ORCID: https://orcid.org/0000-0001-5308-6416)
- Jean‐Alain Fehrentz (ORCID: https://orcid.org/0000-0002-6064-3118)
- Sébastien Clément (ORCID: https://orcid.org/0000-0002-8473-8197)
- Emmanuelle Rémond (ORCID: https://orcid.org/0000-0002-3201-4365)
- Y. Cuminal
- Vladyslava Lunova
Institutions
- École Nationale Supérieure de Chimie de Montpellier (FR)
- Centre National de la Recherche Scientifique (FR)
- Université de Montpellier (FR)
- Institut des Biomolécules Max Mousseron (FR)
- Institut Européen des Membranes (FR)
Publication Details
- Journal
- Bioconjugate Chemistry
- Published
- 2025-09-10
- DOI
- https://doi.org/10.1021/acs.bioconjchem.5c00342
- Primary Topic
- Click Chemistry and Applications
- Type
- article
- Field-Weighted Citation Impact
- 0.00