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CC BY-NC-ND 4.0 · Synthesis 2022; 54(17): 3858-3866
DOI: 10.1055/a-1761-4672
DOI: 10.1055/a-1761-4672
special topic
Special Issue in memory of Prof. Ferenc Fülöp
Beyond the Bioorthogonal Inverse-Electron-Demand Diels–Alder Reactions of Tetrazines: 2-Pyrone-Functionalized Fluorogenic Probes
This work has been implemented with the support provided by the Ministry of Innovation and Technology of Hungary from the National Research, Development and Innovation Fund, financed under the [NKFIH-K-131439 and NKFIH-PD-123955] funding scheme. We are also grateful for the generous support of Eötvös Loránd Research Network (KEP-6, FIKU).
Abstract
The applicability of pyrones as a bioorthogonal platform was explored in inverse-electron-demand Diels–Alder (IEDDA) reactions with a strained cyclooctyne. Studies showed that the pyrones are indeed suitable for IEDDA reactions under physiological conditions. Furthermore, the stable pyrone moiety could be utilized to construct easily accessible fluorogenic probes. Mutual orthogonality of the IEDDA reaction of 2-pyrones with SPAAC reactions of azides was also explored.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1761-4672.
- Supporting Information
Publication History
Received: 15 October 2021
Accepted after revision: 03 January 2022
Accepted Manuscript online:
04 February 2022
Article published online:
06 April 2022
© 2022. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
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