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A native chemical ligation handle that enables the synthesis of advanced activity-based probes: diubiquitin as a case study.


ABSTRACT: We present the development of a native chemical ligation handle that also functions as a masked electrophile that can be liberated during synthesis when required. This handle can thus be used for the synthesis of complex activity-based probes. We describe the use of this handle in the generation of linkage-specific activity-based deubiquitylating enzyme probes that contain substrate context and closely mimic the native ubiquitin isopeptide linkage. We have generated activity-based probes based on all seven isopeptide-linked diubiquitin topoisomers and demonstrated their structural integrity and ability to label DUBs in a linkage-specific manner.

SUBMITTER: Mulder MP 

PROVIDER: S-EPMC4159580 | biostudies-literature |

REPOSITORIES: biostudies-literature

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