Synthesis of C3-Substituted N1-tert-Butyl 1,2,4-Triazinium Salts via the Liebeskind–Srogl Reaction for Fluorogenic Labeling of Live Cells

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F24%3A00581624" target="_blank" >RIV/61388963:_____/24:00581624 - isvavai.cz</a>

Výsledek na webu

<a href="https://doi.org/10.1021/acs.joc.3c02454" target="_blank" >https://doi.org/10.1021/acs.joc.3c02454</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.joc.3c02454" target="_blank" >10.1021/acs.joc.3c02454</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of C3-Substituted N1-tert-Butyl 1,2,4-Triazinium Salts via the Liebeskind–Srogl Reaction for Fluorogenic Labeling of Live Cells

Popis výsledku v původním jazyce

We recently described the development and application of new bioorthogonal conjugation, the triazinium ligation. To explore the wider application of this reaction, in this work we introduce a general method for synthesizing C3-substituted triazinium salts based on the Liebeskind-Srogl cross-coupling reaction and catalytic thioether reduction. These methods enabled the synthesis of triazinium derivatives for investigating the effect of different substituents on the ligation kinetics and stability of the compounds under biologically relevant conditions. Finally, we demonstrate that the combination of coumarin fluorophore attached to position C3 with a C5-(4-methoxyphenyl) substituent, yields a fluorogenic triazinium probes suitable for no-wash, live-cell labeling. The developed methodology represents a promising synthetic approach to the late-stage modification of triazinium salts, potentially widening their application in bioorthogonal reactions.

Název v anglickém jazyce

Synthesis of C3-Substituted N1-tert-Butyl 1,2,4-Triazinium Salts via the Liebeskind–Srogl Reaction for Fluorogenic Labeling of Live Cells

Popis výsledku anglicky

We recently described the development and application of new bioorthogonal conjugation, the triazinium ligation. To explore the wider application of this reaction, in this work we introduce a general method for synthesizing C3-substituted triazinium salts based on the Liebeskind-Srogl cross-coupling reaction and catalytic thioether reduction. These methods enabled the synthesis of triazinium derivatives for investigating the effect of different substituents on the ligation kinetics and stability of the compounds under biologically relevant conditions. Finally, we demonstrate that the combination of coumarin fluorophore attached to position C3 with a C5-(4-methoxyphenyl) substituent, yields a fluorogenic triazinium probes suitable for no-wash, live-cell labeling. The developed methodology represents a promising synthetic approach to the late-stage modification of triazinium salts, potentially widening their application in bioorthogonal reactions.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2024

Kód důvěrnosti údajů

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

Název periodika

Journal of Organic Chemistry

ISSN

0022-3263

e-ISSN

1520-6904

Svazek periodika

89

Číslo periodika v rámci svazku

20

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

7

Strana od-do

14634-14640

Kód UT WoS článku

001162217000001

EID výsledku v databázi Scopus

2-s2.0-85183111224