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Synthesis 2015; 47(18): 2738-2744
DOI: 10.1055/s-0034-1380721
DOI: 10.1055/s-0034-1380721
special topic
Synthesis and Evaluation of Nicotinic Acid Derived Tetrazines for Bioorthogonal Labeling
Further Information
Publication History
Received: 11 March 2015
Accepted: 16 April 2015
Publication Date:
27 May 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201518/lookinside/thumbnails/ss-2015-c0157-st_10-1055_s-0034-1380721-1.jpg)
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 - labelingSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380721.
- Supporting Information
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