Probing the Scope of the Amidine-1,2,3-triazine Cycloaddition as a Prospective Click Ligation Method
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F18%3A00495506" target="_blank" >RIV/61388963:_____/18:00495506 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201800530" target="_blank" >http://dx.doi.org/10.1002/ejoc.201800530</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201800530" target="_blank" >10.1002/ejoc.201800530</a>
Alternative languages
Result language
angličtina
Original language name
Probing the Scope of the Amidine-1,2,3-triazine Cycloaddition as a Prospective Click Ligation Method
Original language description
Despite recent achievements in the development of chemical reactions enabling selective modification of complex biomolecules, the demand for fast and efficient methodologies that allow the attachment of various functional groups to these systems is the subject of intense research. Here, we report on the study of the amidine-1,2,3-triazine cycloaddition reaction, which has the potential to address many of the challenges associated with the development of such chemistry. We describe an optimized protocol leading to the in situ formation of free amidine bases, which directly react in the cycloaddition reaction with 1,2,3-triazines. Our kinetic studies reveal the structural features determining the reaction rates. Finally, we show that the amidine-1,2,3-triazine cycloaddition is extraordinarily selective and orthogonal to other popular ligation reactions. The pros and cons of the methodology are presented.
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
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
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Volume of the periodical
2018
Issue of the periodical within the volume
37
Country of publishing house
DE - GERMANY
Number of pages
5
Pages from-to
5081-5085
UT code for WoS article
000446662900002
EID of the result in the Scopus database
2-s2.0-85054802923