Bioorthogonal Cycloadditions of C3-Trifluoromethylated 1,2,4-Triazines with trans-Cyclooctenes
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F24%3A00585913" target="_blank" >RIV/61388963:_____/24:00585913 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1002/chem.202400839" target="_blank" >https://doi.org/10.1002/chem.202400839</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.202400839" target="_blank" >10.1002/chem.202400839</a>
Alternative languages
Result language
angličtina
Original language name
Bioorthogonal Cycloadditions of C3-Trifluoromethylated 1,2,4-Triazines with trans-Cyclooctenes
Original language description
1,2,4-triazines are a valuable class of heterodienes that can be employed in inverse electron-demand Diels–Alder reactions. However, their broader application in bioorthogonal chemistry is limited due to their low reactivity. This article focuses on 3-(trifluoromethyl)-1,2,4-triazines, which can be efficiently prepared in a one-pot reaction from NH-1,2,3-triazoles. These triazines are highly reactive in reactions with strained cyclooctenes, giving second-order rate constants as high as 230 M–1 s–1. Despite their high reactivity, the compounds remain sufficiently stable under biologically relevant conditions. We show that some of the compounds are fluorogenic, a property of potential use in bioimaging. In addition, we demonstrate the successful application of the triazines in labeling model biomolecules. Our work shows that the reactivity of 1,2,4-triazines can be enhanced by the 3-CF3-substitution, which we consider an important step toward the wider use of this promising class of reagents.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GA24-10829S" target="_blank" >GA24-10829S: Bioorthogonal reactions of 1-alkyl-1,2,4-triazinium salts</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemistry - A European Journal
ISSN
0947-6539
e-ISSN
1521-3765
Volume of the periodical
30
Issue of the periodical within the volume
40
Country of publishing house
DE - GERMANY
Number of pages
5
Pages from-to
e202400839
UT code for WoS article
001253981700001
EID of the result in the Scopus database
2-s2.0-85195422527