The Development of a Versatile Trifunctional Scaffold for Biological Applications

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F15%3A00445393" target="_blank" >RIV/61388963:_____/15:00445393 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1002/ejoc.201500255" target="_blank" >http://dx.doi.org/10.1002/ejoc.201500255</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/ejoc.201500255" target="_blank" >10.1002/ejoc.201500255</a>

Jazyk výsledku

angličtina

Název v původním jazyce

The Development of a Versatile Trifunctional Scaffold for Biological Applications

Popis výsledku v původním jazyce

We describe the synthesis of a trifunctional scaffold constructed from a planar core of trimesic acid derivatized with three propargylamine moieties. The scaffold was attached to a solid-phase resin through the carboxylic group of a fluorinated alkyl spacer arm. The orthogonal protection of two of the alkyne groups with triethylsilyl and triisopropylsilyl moieties enabled modular and efficient derivatization of the scaffold with three different azides by using solid-phase synthesis on amphiphilic ChemMatrix resin. We showed that a fluorine label can be used to quantify the content of fluorine-containing compounds by F-19 NMR spectroscopic analysis after cleavage from the resin. We have thus designed a versatile and convenient tool that could be usefulfor simple and rapid solid-phase syntheses of combinatorial libraries of the scaffold-based compounds, for example as new protein binders.

Název v anglickém jazyce

The Development of a Versatile Trifunctional Scaffold for Biological Applications

Popis výsledku anglicky

We describe the synthesis of a trifunctional scaffold constructed from a planar core of trimesic acid derivatized with three propargylamine moieties. The scaffold was attached to a solid-phase resin through the carboxylic group of a fluorinated alkyl spacer arm. The orthogonal protection of two of the alkyne groups with triethylsilyl and triisopropylsilyl moieties enabled modular and efficient derivatization of the scaffold with three different azides by using solid-phase synthesis on amphiphilic ChemMatrix resin. We showed that a fluorine label can be used to quantify the content of fluorine-containing compounds by F-19 NMR spectroscopic analysis after cleavage from the resin. We have thus designed a versatile and convenient tool that could be usefulfor simple and rapid solid-phase syntheses of combinatorial libraries of the scaffold-based compounds, for example as new protein binders.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

<a href="/cs/project/GA14-17305S" target="_blank" >GA14-17305S: Mimetika insulinu</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2015

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

2015

Číslo periodika v rámci svazku

17

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

13

Strana od-do

3689-3701

Kód UT WoS článku

000355534600008

EID výsledku v databázi Scopus

2-s2.0-84934877597