Design and synthesis of an all-in-one 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group for photo-affinity labeling.
Bioorg Med Chem
; 17(15): 5388-95, 2009 Aug 01.
Article
em En
| MEDLINE
| ID: mdl-19604700
ABSTRACT
A novel radioisotope-free photo-affinity probe containing the 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group was designed and synthesized. This very compact functionality is envisaged to allow photochemically-induced coupling of a compound to its target followed by click reaction coupling with an azido-biotin reagent in order to facilitate purification of the labeled target. In a proof-of-concept study we have shown that 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group could be photolyzed to efficiently furnish the methanol adduct 23 and that the generated highly unstable carbene does not react with the neighboring acetylene moiety. A subsequent click reaction with the azido-biotin derivative 25 proceeded smoothly to give triazole 26. This chemical probe should thus be of unique value for facilitating identification of the molecular structure of the target of a bioactive compound.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Azirinas
/
Marcadores de Fotoafinidade
/
Hidrocarbonetos Fluorados
Idioma:
En
Ano de publicação:
2009
Tipo de documento:
Article