» Articles » PMID: 25895752

Galacto Configured N-aminoaziridines: a New Type of Irreversible Inhibitor of β-galactosidases

Overview
Journal Org Biomol Chem
Specialties Biochemistry
Chemistry
Date 2015 Apr 22
PMID 25895752
Citations 6
Authors
Affiliations
Soon will be listed here.
Abstract

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.

Citing Articles

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.


Radiosynthesis and Early Evaluation of a Positron Emission Tomography Imaging Probe [F]AGAL Targeting Alpha-Galactosidase A Enzyme for Fabry Disease.

Lohith T, Kaittanis C, Belanger A, Ahn S, Sandoval P, Cohen L Molecules. 2023; 28(20).

PMID: 37894622 PMC: 10609273. DOI: 10.3390/molecules28207144.


Side Chain Conformation and Its Influence on Glycosylation Selectivity in Hexo- and Higher Carbon Furanosides.

Siyabalapitiya Arachchige S, Crich D J Org Chem. 2021; 87(1):316-339.

PMID: 34905382 PMC: 8741747. DOI: 10.1021/acs.joc.1c02374.


Recent advances in activity-based probes (ABPs) and affinity-based probes (ABPs) for profiling of enzymes.

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.


Direct Stereoselective Aziridination of Cyclohexenols with 3-Amino-2-(trifluoromethyl)quinazolin-4(3)-one in the Synthesis of Cyclitol Aziridine Glycosidase Inhibitors.

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.