Second-generation difluorinated cyclooctynes for copper-free click chemistry.
J Am Chem Soc
; 130(34): 11486-93, 2008 Aug 27.
Article
em En
| MEDLINE
| ID: mdl-18680289
ABSTRACT
The 1,3-dipolar cycloaddition of azides and activated alkynes has been used for site-selective labeling of biomolecules in vitro and in vivo. While copper catalysis has been widely employed to activate terminal alkynes for [3 + 2] cycloaddition, this method, often termed "click chemistry", is currently incompatible with living systems because of the toxicity of the metal. We recently reported a difluorinated cyclooctyne (DIFO) reagent that rapidly reacts with azides in living cells without the need for copper catalysis. Here we report a novel class of DIFO reagents for copper-free click chemistry that are considerably more synthetically tractable. The new analogues maintained the same elevated rates of [3 + 2] cycloaddition as the parent compound and were used for imaging glycans on live cells. These second-generation DIFO reagents should expand the use of copper-free click chemistry in the hands of biologists.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Polissacarídeos
/
Azidas
/
Membrana Celular
/
Cobre
/
Alcinos
/
Hidrocarbonetos Cíclicos
/
Hidrocarbonetos Fluorados
Limite:
Animals
/
Humans
Idioma:
En
Ano de publicação:
2008
Tipo de documento:
Article