The discovery of pyridinium 1,2,4-triazines with enhanced performance in bioconjugation reactions

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

The discovery of pyridinium 1,2,4-triazines with enhanced performance in bioconjugation reactions

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

The discovery of pyridinium 1,2,4-triazines with enhanced performance in bioconjugation reactions

Popis výsledku anglicky

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.

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

2017

Kód důvěrnosti údajů

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

Název periodika

Chemical Science

ISSN

2041-6520

e-ISSN

—

Svazek periodika

8

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

6

Strana od-do

3593-3598

Kód UT WoS článku

000400553000034

EID výsledku v databázi Scopus

2-s2.0-85021631138