Cell-Penetrating Peptides Containing Fluorescent d-Cysteines
- Navo, C.D. 2
- Asín, A. 2
- Gómez-Orte, E. 1
- Gutiérrez-Jiménez, M.I. 2
- Compañón, I. 2
- Ezcurra, B. 1
- Avenoza, A. 2
- Busto, J.H. 2
- Corzana, F. 2
- Zurbano, M.M. 2
- Jiménez-Osés, G. 2
- Cabello, J. 1
- Peregrina, J.M. 2
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1
Centro de Investigación Biomédica de La Rioja
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2
Universidad de La Rioja
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ISSN: 0947-6539
Año de publicación: 2018
Volumen: 24
Número: 31
Páginas: 7991-8000
Tipo: Artículo
beta Ver similares en nube de resultadosOtras publicaciones en: Chemistry - A European Journal
Proyectos relacionados
2015/00062/001
Resumen
A series of fluorescent d-cysteines (Cys) has been synthesized and their optical properties were studied. The key synthetic step is the highly diastereoselective 1,4-conjugate addition of aryl thiols to a chiral bicyclic dehydroalanine recently developed by our group. This reaction is fast at room temperature and proceeds with total chemo- and stereoselectivity. The Michael adducts were easily transformed into the corresponding amino acids to study their optical properties and, in some selected cases, into the corresponding N-Fmoc-d-cysteine derivatives to be used in solid-phase peptide synthesis (SPPS). To further demonstrate the utility of these non-natural Cys-derived fluorescent amino acids, the coumaryl and dansyl derivatives were incorporated into cell-penetrating peptide sequences through standard SPPS and their optical properties were studied in different cell lines. The internalization of these fluorescent peptides was monitored by fluorescence microscopy. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim