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http://hdl.handle.net/2445/193021
Title: | Amino acids with fluorescent tetrazine ethers as bioorthogonal handles for peptide modification |
Author: | Ros, Enric Bellido, Marina Matarin, Joan A. Gallen, Albert Martínez, Manuel Rodríguez, Laura Verdaguer i Espaulella, Xavier Ribas de Pouplana, Lluis Riera i Escalé, Antoni |
Keywords: | Aminoàcids Fluorescència Amino acids Fluorescence |
Issue Date: | 12-May-2022 |
Publisher: | Royal Society of Chemistry |
Abstract: | A set of 3-bromo-1,2,4,5-tetrazines with three distinct substitutions have been used as reagents for late-stage functionalization of small molecules through nucleophilic aromatic substitution. Spectroscopic studies of the products obtained proved that tetrazine ethers are intrinsically fluorescent. This fluorescence is lost upon inverse Electron-Demand Diels-Alder (iEDDA) cycloaddition with strained alkenes. Tetrazine-phenol ethers are rather interesting because they can undergo rapid iEDDA reactions with a second order rate constant (k2) compatible with bioorthogonal ligations. As a showcase, L-tyrosine was derivatized with 3-bromo-6-methyl-1,2,4,5-tetrazine and coupled to the peptide drug octreotide. This peptide was detected in cellular flow cytometry, and its fluorescence turned off through a bioorthogonal iEDDA cycloaddition with a strained alkene, showing for the first time the detection and reactivity of intrinsically fluorescent tetrazines in a biologically relevant context. The synthesis and characterization of fluorescent tetrazine ethers with bioorthogonal applicability pave the way for the generation of useful compounds for both detection and bioconjugation in vivo. |
Note: | Reproducció del document publicat a: https://doi.org/10.1039/D2RA02531K |
It is part of: | RSC Advances, 2022, vol. 12, num. 23, p. 14321-14327 |
URI: | http://hdl.handle.net/2445/193021 |
Related resource: | https://doi.org/10.1039/D2RA02531K |
ISSN: | 2046-2069 |
Appears in Collections: | Articles publicats en revistes (Química Inorgànica i Orgànica) |
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