Probing the Scope of the Amidine-1,2,3-triazine Cycloaddition as a Prospective Click Ligation Method

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Probing the Scope of the Amidine-1,2,3-triazine Cycloaddition as a Prospective Click Ligation Method

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Probing the Scope of the Amidine-1,2,3-triazine Cycloaddition as a Prospective Click Ligation Method

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GJ15-06020Y" target="_blank" >GJ15-06020Y: Vývoj nových bioortogonálních reakcí</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2018

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

—

Svazek periodika

2018

Číslo periodika v rámci svazku

37

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

5

Strana od-do

5081-5085

Kód UT WoS článku

000446662900002

EID výsledku v databázi Scopus

2-s2.0-85054802923