Cysteine/Penicillamine Ligation Independent of Terminal Steric Demands for Chemical Protein Synthesis.
Angew Chem Int Ed Engl
; 59(31): 12741-12745, 2020 07 27.
Article
em En
| MEDLINE
| ID: mdl-32343022
ABSTRACT
The chemical ligation of two unprotected peptides to generate a natural peptidic linkage specifically at the C- and N-termini is a desirable goal in chemical protein synthesis but is challenging because it demands high reactivity and selectivity (chemo-, regio-, and stereoselectivity). We report an operationally simple and highly effective chemical peptide ligation involving the ligation of peptides with C-terminal salicylaldehyde esters to peptides with N-terminal cysteine/penicillamine. The notable features of this method include its tolerance of steric hinderance from the side groups on either ligating terminus, thereby allowing flexible disconnection at sites that are otherwise difficult to functionalize. In addition, this method can be expanded to selective desulfurization and one-pot ligation-desulfurization reactions. The effectiveness of this method was demonstrated by the synthesis of VISTA (216-311), PD-1 (192-288) and Eglinâ
C.
Palavras-chave
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Penicilamina
/
Fragmentos de Peptídeos
/
Cisteína
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Ano de publicação:
2020
Tipo de documento:
Article