Galacto Configured N-aminoaziridines: a New Type of Irreversible Inhibitor of β-galactosidases
Overview
Chemistry
Affiliations
A new type of galactose mimetics has been synthesized following a straightforward synthetic approach based on cyclohexene olefin aziridination reactions directed by hydroxyl substituents. These enantiomerically pure galacto-configured N-aminoaziridines are potent irreversible inhibitors of Aspergillus oryzae and Escherichia coliβ-galactosidases.
From Mechanism-Based Retaining Glycosidase Inhibitors to Activity-Based Glycosidase Profiling.
Artola M, Aerts J, van der Marel G, Rovira C, Codee J, Davies G J Am Chem Soc. 2024; 146(36):24729-24741.
PMID: 39213505 PMC: 11403624. DOI: 10.1021/jacs.4c08840.
Lohith T, Kaittanis C, Belanger A, Ahn S, Sandoval P, Cohen L Molecules. 2023; 28(20).
PMID: 37894622 PMC: 10609273. DOI: 10.3390/molecules28207144.
Siyabalapitiya Arachchige S, Crich D J Org Chem. 2021; 87(1):316-339.
PMID: 34905382 PMC: 8741747. DOI: 10.1021/acs.joc.1c02374.
Fang H, Peng B, Ong S, Wu Q, Li L, Yao S Chem Sci. 2021; 12(24):8288-8310.
PMID: 34221311 PMC: 8221178. DOI: 10.1039/d1sc01359a.
Artola M, Wouters S, Schroder S, de Boer C, Chen Y, Petracca R European J Org Chem. 2019; 2019(6):1397-1404.
PMID: 31787842 PMC: 6876648. DOI: 10.1002/ejoc.201801703.