The discovery of pyridinium 1,2,4-triazines with enhanced performance in bioconjugation reactions
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F17%3A00475538" target="_blank" >RIV/61388963:_____/17:00475538 - isvavai.cz</a>
Result on the web
<a href="http://pubs.rsc.org/en/content/articlehtml/2017/sc/c6sc05442k" target="_blank" >http://pubs.rsc.org/en/content/articlehtml/2017/sc/c6sc05442k</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/c6sc05442k" target="_blank" >10.1039/c6sc05442k</a>
Alternative languages
Result language
angličtina
Original language name
The discovery of pyridinium 1,2,4-triazines with enhanced performance in bioconjugation reactions
Original language description
1,2,4-Triazines have recently been identified as versatile dienes participating in the inverse electron-demand Diels-Alder reaction with strained dienophiles. However, their widespread utility in bioconjugation reactions is still limited. Herein, we report a systematic study on the reactivity of various 1,2,4-triazines with trans-cyclooctenes showing that the structure of both the triazine and the dienophile significantly affect the reaction rate. Our kinetic study led to the discovery of novel cationic 1,2,4-triazines with superior properties for bioconjugation reactions. We have developed an efficient method that enables their late-stage functionalization and allows for easy access to various useful heterobifunctional scaffolds. In addition, these charged dienes form unprecedented fluorescent products upon reaction with trans-cyclooctenes and can be used for fluorogenic labeling of subcellular compartments in live cells.
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/GJ15-06020Y" target="_blank" >GJ15-06020Y: Development of new bioorthogonal reactions</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemical Science
ISSN
2041-6520
e-ISSN
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Volume of the periodical
8
Issue of the periodical within the volume
5
Country of publishing house
GB - UNITED KINGDOM
Number of pages
6
Pages from-to
3593-3598
UT code for WoS article
000400553000034
EID of the result in the Scopus database
2-s2.0-85021631138