HA-Ahx-Ahx-Ub-VPS

a potent, irreversible and specific inhibitor of deubiquitinating enzymes (DUBs), labeled with HA on the N-terminus

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Description

HA-Ahx-Ahx-Ub-VPS (UbiQ-193) is an irreversible inhibitor of deubiquitinating enzymes (DUBs) that is prepared by chemical synthesis. It contains a vinyl pentynyl sulfone (VPS) warhead and N-terminal HA-tag (YPYDVPDYA). The HA tag is separated from the Ub N-terminus by two aminohexanoic acid (Ahx) linkers for efficient recognition of the tag. The VPS electrophile allows for post-labeling modification of covalent DUB::UbiQ-193 complexes by using click chemistry with for example biotin-azide.

El Oualid, F., et al. Chemical Synthesis of Ubiquitin, Ubiquitin-Based Probes, and Diubiquitin. Angewandte Chemie Int. Ed. 49, 10149-10153 (2010).
http://www.ncbi.nlm.nih.gov/pubmed/21117055

Borodovsky, A., et al. A novel active site-directed probe specific for deubiquitylating enzymes reveals proteasome association of USP14. EMBO J. 20, 5187-5196 (2001).
http://www.ncbi.nlm.nih.gov/pubmed/11566882

Borodovsky, A., et al. Chemistry-based functional proteomics reveals novel members of the deubiquitinating enzyme family. Chem. Biol. 9, 1149-1159 (2002).
http://www.ncbi.nlm.nih.gov/pubmed/12401499

de Jong, A., et al. Ubiquitin-based probes prepared by total synthesis to profile the activity of deubiquitinating enzymes. ChemBiochem 13, 2251-2258 (2012).
http://www.ncbi.nlm.nih.gov/pubmed/23011887

http://www.ncbi.nlm.nih.gov/pubmed/23011887