Towards broad spectrum activity - based glycosidase probes : synthesis and evaluation of deoxygenated cyclophellitol aziridines
نویسندگان
چکیده
منابع مشابه
Towards broad spectrum activity-based glycosidase probes: synthesis and evaluation of deoxygenated cyclophellitol aziridines.
Activity-based protein profiling has emerged as a powerful tool for visualizing glycosidases in complex biological samples. Several configurational cyclophellitol isomers have been shown to display high selectivity as probes for glycosidases processing substrates featuring the same configuration. Here, a set of deoxygenated cyclophellitols are presented which enable inter-class profiling of β-g...
متن کامل1,6-Cyclophellitol Cyclosulfates: A New Class of Irreversible Glycosidase Inhibitor
The essential biological roles played by glycosidases, coupled to the diverse therapeutic benefits of pharmacologically targeting these enzymes, provide considerable motivation for the development of new inhibitor classes. Cyclophellitol epoxides and aziridines are recently established covalent glycosidase inactivators. Inspired by the application of cyclic sulfates as electrophilic equivalents...
متن کاملCorrection to “Detection of Active Mammalian GH31 α-Glucosidases in Health and Disease Using In-Class, Broad-Spectrum Activity-Based Probes”
The development of small molecule activity-based probes (ABPs) is an evolving and powerful area of chemistry. There is a major need for synthetically accessible and specific ABPs to advance our understanding of enzymes in health and disease. α-Glucosidases are involved in diverse physiological processes including carbohydrate assimilation in the gastrointestinal tract, glycoprotein processing i...
متن کاملIn vitro and in vivo comparative and competitive activity-based protein profiling of GH29 α-l-fucosidases.
GH29 α-l-fucosidases catalyze the hydrolysis of α-l-fucosidic linkages. Deficiency in human lysosomal α-l-fucosidase (FUCA1) leads to the recessively inherited disorder, fucosidosis. Herein we describe the development of fucopyranose-configured cyclophellitol aziridines as activity-based probes (ABPs) for selective in vitro and in vivo labeling of GH29 α-l-fucosidases from bacteria, mice and ma...
متن کاملStereocontrolled synthesis of beta-amino alcohols from lithiated aziridines and boronic esters.
From natural products to ligands for asymmetric catalysis, the b-amino alcohol motif is ubiquitous. The importance of this motif to such a broad spectrum of chemistry has prompted the development of a range of methodologies for its synthesis which include Sharpless aminohydroxylation as well as the addition of nucleophiles to aminocarbonyls, imines, epoxides, and aziridines. We considered a con...
متن کامل