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

Authors :
Mulder MP
El Oualid F
ter Beek J
Ovaa H
Source :
Chembiochem : a European journal of chemical biology [Chembiochem] 2014 May 05; Vol. 15 (7), pp. 946-9. Date of Electronic Publication: 2014 Mar 12.
Publication Year :
2014

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.<br /> (© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.)

Details

Language :
English
ISSN :
1439-7633
Volume :
15
Issue :
7
Database :
MEDLINE
Journal :
Chembiochem : a European journal of chemical biology
Publication Type :
Academic Journal
Accession number :
24623714
Full Text :
https://doi.org/10.1002/cbic.201402012