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CC BY-NC-ND 4.0 · Synthesis 2022; 54(17): 3858-3866
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

Gergely B. Cserép∗
a   Chemical Biology Research Group, Institute of Organic Chemistry, ELKH Research Centre for Natural Sciences, Magyar Tudósok Krt 2., 1117 Budapest, Hungary
,
Krisztina Németh
a   Chemical Biology Research Group, Institute of Organic Chemistry, ELKH Research Centre for Natural Sciences, Magyar Tudósok Krt 2., 1117 Budapest, Hungary
,
Ágnes Szatmári
a   Chemical Biology Research Group, Institute of Organic Chemistry, ELKH Research Centre for Natural Sciences, Magyar Tudósok Krt 2., 1117 Budapest, Hungary
,
Flóra Horváth
a   Chemical Biology Research Group, Institute of Organic Chemistry, ELKH Research Centre for Natural Sciences, Magyar Tudósok Krt 2., 1117 Budapest, Hungary
,
Tímea Imre
b   MS Metabolomics Research Group, Centre for Structural Study, ELKH Research Centre for Natural Sciences, Magyar Tudósok Krt 2., 1117 Budapest, Hungary
,
Krisztina Németh
b   MS Metabolomics Research Group, Centre for Structural Study, ELKH Research Centre for Natural Sciences, Magyar Tudósok Krt 2., 1117 Budapest, Hungary
,
Péter Kele∗
a   Chemical Biology Research Group, Institute of Organic Chemistry, ELKH Research Centre for Natural Sciences, Magyar Tudósok Krt 2., 1117 Budapest, Hungary
› Author AffiliationsThis 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).
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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.

Key words

IEDDA - bioorthogonal - 2-pyrone - fluorogenic probes - protein labeling

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. The Author(s). 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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