Site-Selective Synthesis of Insulin Azides and Bioconjugates.
Bioconjug Chem
; 30(4): 1127-1132, 2019 04 17.
Article
em En
| MEDLINE
| ID: mdl-30946565
ABSTRACT
A synthetic method to access novel azido-insulin analogs directly from recombinant human insulin (RHI) was developed via diazo-transfer chemistry using imidazole-1-sulfonyl azide. Systematic optimization of reaction conditions led to site-selective azidation of amino acids B1-phenylalanine and B29-lysine present in RHI. Subsequently, the azido-insulin analogs were used in azide-alkyne [3 + 2] cycloaddition reactions to synthesize a diverse array of triazole-based RHI bioconjugates that were found to be potent human insulin receptor binders. The utility of this method was further demonstrated by the concise and controlled synthesis of a heterotrisubstituted insulin conjugate.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Azidas
/
Insulina
Idioma:
En
Ano de publicação:
2019
Tipo de documento:
Article
País de afiliação:
Estados Unidos