N-Terminal dual protein functionalization by strain-promoted alkyne-nitrone cycloaddition.
Org Biomol Chem
; 11(17): 2772-9, 2013 May 07.
Article
em En
| MEDLINE
| ID: mdl-23487244
ABSTRACT
Strain-promoted alkyne-nitrone cycloadditon (SPANC) was optimized as a versatile strategy for dual functionalization of peptides and proteins. The usefulness of the dual labeling protocol is first exemplified by the simultaneous introduction of a chloroquine and a stearyl moiety, two endosomal escape-improving functional groups, into the cell-penetrating peptide hLF (human lactoferrin). Additionally, we demonstrate that dual labeling of proteins is feasible by combining metal-free and copper-catalyzed click chemistry. First, SPANC is applied to enhanced green fluorescent protein to introduce both biotin and a terminal alkyne. The terminal acetylene then serves as a convenient anchor point for the CuAAC reaction with azido-containing fluorescein, thereby demonstrating the potential of combined SPANC and CuAAC for the straightforward, dual functionalization of proteins.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Biotina
/
Proteínas de Fluorescência Verde
/
Alcinos
/
Lactoferrina
/
Óxidos de Nitrogênio
Limite:
Humans
Idioma:
En
Ano de publicação:
2013
Tipo de documento:
Article