Access to Galectin-3 Inhibitors from Chemoenzymatic Synthons.
J Org Chem
; 85(24): 16099-16114, 2020 12 18.
Article
en En
| MEDLINE
| ID: mdl-33200927
ABSTRACT
Chemoenzymatic strategies are useful for providing both regio- and stereoselective access to bioactive oligosaccharides. We show herein that a glycosynthase mutant of a Thermus thermophilus α-glycosidase can react with unnatural glycosides such as 6-azido-6-deoxy-d-glucose/glucosamine to lead to ß-d-galactopyranosyl-(1â3)-d-glucopyranoside or ß-d-galactopyranosyl-(1â3)-2-acetamido-2-deoxy-d-glucopyranoside derivatives bearing a unique azide function. Taking advantage of the orthogonality between the azide and the hydroxyl functional groups, the former was next selectively reacted to give rise to a library of galectin-3 inhibitors. Combining enzyme substrate promiscuity and bioorthogonality thus appears as a powerful strategy to rapidly access to sugar-based ligands.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Oligosacáridos
/
Galectina 3
Idioma:
En
Revista:
J Org Chem
Año:
2020
Tipo del documento:
Article
País de afiliación:
Francia