From covalent glycosidase inhibitors to activity-based glycosidase probes
| Autor: | Sybrin P. Schröder, Hermen S. Overkleeft, Gijsbert A. van der Marel, Johannes M. F. G. Aerts, Martin D. Witte, Lianne I. Willems, Jianbing Jiang, Jeroen D. C. Codée, Kah-Yee Li, Thomas J. N. Beenakker, Wouter W. Kallemeijn |
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| Přispěvatelé: | Chemical Biology 2, Medical Biochemistry, Amsterdam Cardiovascular Sciences, Amsterdam Gastroenterology Endocrinology Metabolism |
| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Proteases
Glycoside Hydrolases TERMINAL ALKYNES medicine.medical_treatment enzymes Chemical biology SELECTIVE INHIBITORS glycosidases Context (language use) protein profiling Catalysis BETA-GLUCOSIDASES Serine PROFILING PROBES glycobiology CARBOHYDRATE-PROCESSING ENZYMES medicine Glycoside hydrolase Enzyme Inhibitors CYCLOPHELLITOL ANALOGS chemistry.chemical_classification Protease Molecular Structure FUNCTIONAL PROTEOMIC ANALYSIS Organic Chemistry Glycosidic bond General Chemistry ALPHA-GLUCOSIDASE proteins PROTEIN-TYROSINE PHOSPHATASES CATALYTIC NUCLEOPHILE Enzyme Activation Enzyme chemistry Biochemistry Drug Design Molecular Probes |
| Zdroj: | Chemistry, 20(35), 10864-10872. Wiley-VCH Verlag GmbH & Co. KGaA Chemistry (Weinheim an der Bergstrasse, Germany), 20(35), 10864-10872. Wiley-VCH Verlag |
| ISSN: | 0947-6539 |
| Popis: | Activity-based protein profiling has emerged as a powerful discovery tool in chemical biology and medicinal chemistry research. Success of activity-based protein profiling hinges on the presence of compounds that can covalently and irreversibly bind to enzymes, do so selectively in the context of complex biological samples, and subsequently report on the selected pool of proteins. Such tagged molecules featuring an electrophilic trap, termed activity-based probes, have been developed with most success for serine hydrolases and various protease families (serine proteases, cysteine proteases, proteasomes). This concept presents the current progress and future directions in the design of activity-based probes targeting retaining glycosidases, enzymes that employ a double displacement mechanism in the hydrolysis of glycosidic bonds with overall retention. In contrast to inverting glycosidases, retaining glycosidases form a covalent intermediate with their substrates during the catalytic process and are therefore amenable to activity-based protein profiling studies. |
| Databáze: | OpenAIRE |
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