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A General Approach Towards Triazole‐Linked Adenosine Diphosphate Ribosylated Peptides and Proteins
Author(s) -
Liu Qiang,
Kistemaker Hans A. V.,
Bhogaraju Sagar,
Dikic Ivan,
Overkleeft Herman S.,
van der Marel Gijsbert A.,
Ovaa Huib,
van der Heden van Noort Gerbrand J.,
Filippov Dmitri V.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201710527
Subject(s) - peptide , chemistry , click chemistry , biochemistry , combinatorial chemistry
Current methods to prepare adenosine diphosphate ribosylated (ADPr) peptides are not generally applicable due to the labile nature of this post‐translational modification and its incompatibility with strong acidic conditions used in standard solid‐phase peptide synthesis. A general strategy is presented to prepare ADPr peptide analogues based on a copper‐catalyzed click reaction between an azide‐modified peptide and an alkyne‐modified ADPr counterpart. The scope of this approach was expanded to proteins by preparing two ubiquitin ADPr analogues carrying the biological relevant α‐glycosidic linkage. Biochemical validation using Legionella effector enzyme SdeA shows that clicked ubiquitin ADPr is well‐tolerated and highlights the potential of this strategy to prepare ADPr proteins.