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Synlett 2017; 28(15): 1939-1943
DOI: 10.1055/s-0036-1588744
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Ubiquitinated Histone Mimic Bearing a New Thioether Linkage

Qiaoqiao He
a   Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen 518055, P. R. of China
c   Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, P. R. of China   Email: huhonggang_fox@msn.com
,
Yunkun Qi
b   School of Life Sciences, University of Science and Technology of China, Hefei 230027, P. R. of China   Email: ljbchem@163.com
,
Chao Liu
c   Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, P. R. of China   Email: huhonggang_fox@msn.com
,
Jiabin Li*
b   School of Life Sciences, University of Science and Technology of China, Hefei 230027, P. R. of China   Email: ljbchem@163.com
,
Honggang Hu*
c   Department of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, P. R. of China   Email: huhonggang_fox@msn.com
› Author Affiliations
Further Information

Publication History

Received: 17 January 2017

Accepted after revision: 19 February 2017

Publication Date:
09 March 2017 (online)

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Published as part of the Cluster Recent Advances in Protein and Peptide Synthesis

Abstract

Current studies on histone ubiquitination require the development of more effective approaches for the preparation of ubiquitinated histones. Here, we report a new approach to obtain ubiquitinated histone mimics by using a thioether linkage. The synthetic ubiquitinated histone mimic is stable under reducing conditions and has the same atom number as the native structure. Biochemical experiments showed that the mimic is a good surrogate for natural ubiquitinated histone.

Key words

ubiquitin - histone modification - thioether linkage - nucleosome - thermal stability

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588744.
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