Synthesis and Evaluation of Nicotinic Acid Derived Tetrazines for Bioorthogonal Labeling

Gergely B. Cserép; Orsolya Demeter; Effi Bätzner; Mihály Kállay; Hans-Achim Wagenknecht; Péter Kele

doi:10.1055/s-0034-1380721

Synthesis, Table of Contents

Synthesis 2015; 47(18): 2738-2744
DOI: 10.1055/s-0034-1380721

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Synthesis and Evaluation of Nicotinic Acid Derived Tetrazines for Bioorthogonal Labeling

Gergely B. Cserép

^aChemical Biology Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary Email: kele.peter@ttk.mta.hu

,

Orsolya Demeter

^aChemical Biology Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary Email: kele.peter@ttk.mta.hu

,

Effi Bätzner

^bInstitute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany Email: Wagenknecht@kit.edu

,

Mihály Kállay

^cMTA-BME ‘Lendület’ Quantum Chemistry Research Group, Department of Physical Chemistry and Materials Science, Budapest University of Technology and Economics, P. O. Box 91, 1521 Budapest, Hungary

,

Hans-Achim Wagenknecht*

^bInstitute of Organic Chemistry, Karlsruhe Institute of Technology (KIT), Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany Email: Wagenknecht@kit.edu

,

Péter Kele*

^aChemical Biology Research Group, Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, Magyar tudósok krt. 2, 1117, Budapest, Hungary Email: kele.peter@ttk.mta.hu

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Abstract

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Abstract

A set of nicotinic acid derived tetrazines were synthesized and evaluated for activity in inverse-electron-demand Diels–Alder (IEDDA) reactions with various dienophiles. It was found that the performance of these tetrazines is governed by two factors. Theoretical and experimental investigations showed that steric effects may override the energetically predicted order of reactivity. Making a compromise between reactivity and stability, a selected tetrazine was incorporated into a deoxynucleotide to afford a bioorthogonalized building block enabling IEDDA-based tagging schemes of nucleic acids.

Key words

tetrazine - inverse-electron-demand Diels–Alder reaction - biorthogonal - nucleic acid - labeling

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References

References
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