Synthesis of a Ubiquitinated Histone Mimic Bearing a New Thioether Linkage

Qiaoqiao He; Yunkun Qi; Chao Liu; Jiabin Li; Honggang Hu

doi:10.1055/s-0036-1588744

Synlett, Table of Contents

Synlett 2017; 28(15): 1939-1943
DOI: 10.1055/s-0036-1588744

cluster

Synthesis of a Ubiquitinated Histone Mimic Bearing a New Thioether Linkage

Qiaoqiao He

^aKey Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen 518055, P. R. of China

^cDepartment of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, P. R. of China Email: huhonggang_fox@msn.com

,

Yunkun Qi

^bSchool of Life Sciences, University of Science and Technology of China, Hefei 230027, P. R. of China Email: ljbchem@163.com

,

Chao Liu

^cDepartment of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, P. R. of China Email: huhonggang_fox@msn.com

,

Jiabin Li*

^bSchool of Life Sciences, University of Science and Technology of China, Hefei 230027, P. R. of China Email: ljbchem@163.com

,

Honggang Hu*

^cDepartment of Organic Chemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, P. R. of China Email: huhonggang_fox@msn.com

› Author Affiliations

Abstract

All articles of this category

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

Full Text

References

References and Notes
1 Huang H. Sabari BR. Garcia BA. Allis CD. Zhao Y.-M. Cell 2014; 159: 458

2a Zhang Y. Genes Dev. 2003; 17: 2733
2b Weake VM. Workman JL. Mol. Cell. 2008; 29: 653
2c Müller MM. Muir TW. Chem. Rev. 2015; 115: 2296

3a Mattiroli F. Vissers JH. A. van Dijk WJ. Ikpa P. Citterio E. Vermeulen W. Marteijn JA. Sixma TK. Cell 2012; 150: 1182
3b Wilson MD. Benlekbir S. Fradet-Turcotte A. Sherker A. Julien J.-P. McEwan A. Noordermeer SM. Sicheri F. Rubinstein JL. Durocher D. Nature 2016; 536: 100

4a Fierz B. Chatterjee C. McGinty RK. Bar-Dagan M. Raleigh DP. Muir TW. Nat. Chem. Biol. 2011; 7: 113
4b Debelouchina G. Gerecht K. Muir TW. Nat. Chem. Biol. 2017; 13: 105

5a Morgan MT. Haj-Yahya M. Ringel AE. Bandi P. Brik A. Wolberger C. Science 2016; 351: 725
5b Machida S. Sekine S. Nishiyama Y. Horikoshi N. Kurumizaka H. Open Biol. 2016; 6: 160090
5c Li J.-B. He Q.-Q. Liu Y.-T. Liu S.-L. Tang S. Li C.-M. Sun D.-M. Li X.-R. Zhou M. Zhu P. Bi G.-Q. Zhou Z.-H. Zheng J.-S. Tian C.-L. ChemBioChem 2016; 18: 176

6a Kent SB. H. Chem. Soc. Rev. 2009; 38: 338
6b Pattabiraman VR. Bode JW. Nature 2011; 480: 471
6c Zheng J.-S. Tang S. Huang Y.-C. Liu L. Acc. Chem. Res. 2013; 46: 2475
6d Huang YC. Fang GM. Liu L. Nat. Sci. Rev. 2016; 3: 107
6e Bondalapati S. Jbara M. Brik A. Nat. Chem. 2016; 8: 407

7a Siman P. Karthikeyan SV. Nikolov M. Fischle W. Brik A. Angew. Chem. Int. Ed. 2013; 52: 8059
7b Seenaiah M. Jbara M. Mali SM. Brik A. Angew. Chem. Int. Ed. 2015; 54: 12374

8a McGinty RK. Kim J. Chatterjee C. Roeder RG. Muir TW. Nature 2008; 453: 812
8b Kumar KS. A. Spasser L. Ohayon S. Erlich LA. Brik A. Bioconjugate Chem. 2011; 22: 137
8c Haj-Yahya M. Eltarteer N. Ohayon S. Shema E. Kotler E. Oren M. Brik A. Angew. Chem. Int. Ed. 2012; 51: 11535
8d Holt M. Muir T. Annu. Rev. Biochem. 2015; 84: 265
8e Weller CE. Dhall A. Ding F. Linares E. Whedon SD. Senger NA. Tyson EL. Bagert JD. Li X. Augusto O. Chatterjee C. Nat. Commun. 2016; 7: 12979

9 Bi X.-B. Yang R.-L. Feng XY. Rhodes D. Liu C.-F. Org. Biomol. Chem. 2016; 14: 835
10 Dawson PE. Muir TW. Clark-Lewis I. Kent SB. H. Science 1994; 266: 776

11a Chatterjee C. McGinty RK. Fierz B. Muir TW. Nat. Chem. Biol. 2010; 6: 267
11b Whitcomb SJ. Fierz B. McGinty RK. Holt M. Ito T. Muir TW. Allis CD. J. Biol. Chem. 2012; 287: 23718
11c Holt MT. David Y. Pollock S. Tang Z. Jeon J. Kim J. Roeder RG. Muir TW. Proc. Natl. Acad. Sci. U.S.A. 2015; 112: 10365
11d Zhou L. Holt MT. Ohashi N. Zhao A. Müller MM. Wang B. Muir TW. Nat. Commun. 2016; 7: 10589

12 Long L. Furgason M. Yao TT. Methods 2014; 70: 134

13a Simon MD. Chu F. Racki LR. de la Cruz CC. Burlingame AL. Panning B. Narlikar GJ. Shokat KM. Cell 2007; 128: 1003
13b Chatterjee C. Muir TW. J. Biol. Chem. 2010; 285: 11045
13c Dhall A. Chatterjee C. ACS Chem. Biol. 2011; 6: 987

14a Yang R.-L. Bi X.-B. Li FP. Cao Y. Liu C.-F. Chem. Commun. 2014; 50: 7971
14b Li Y.-T. Liang J. Li J.-B. Fang G.-M. Huang Y. Liu L. J. Pept. Sci. 2014; 20: 102

15 Hemantha HP. Bavikar SN. Herman-Bachinsky Y. Haj-Yahya N. Bondalapati S. Ciechanover A. Brik A. J. Am. Chem. Soc. 2014; 136: 2665

16a Wu L.-P. Zee BM. Wang Y.-M. Garcia BA. Dou Y.-L. Mol. Cell. 2011; 43: 132
16b Wu L.-P. Lee SY. Zhou B. Nguyen UT. Muir TW. Tan S. Dou Y.-L. Mol. Cell. 2013; 49: 1108
16c Wu L.-P. Li L. Zhou B. Qin Z.-H. Dou Y.-L. Mol. Cell. 2014; 54: 920

17a Fang G.-M. Li Y.-M. Shen F. Huang Y.-C. Li J.-B. Lin Y. Cui H.-K. Liu L. Angew. Chem. Int. Ed. 2011; 50: 7645
17b Fang G.-M. Wang J.-X. Liu L. Angew. Chem. Int. Ed. 2012; 51: 10347
17c Li Y.-M. Li Y.-T. Pan M. Kong X.-Q. Huang Y.-C. Hong Z.-Y. Liu L. Angew. Chem. Int. Ed. 2014; 53: 2198
17d Tang S. Si Y.-Y. Wang Z.-P. Mei K.-R. Chen X. Cheng J.-Y. Zheng J.-S. Liu L. Angew. Chem. Int. Ed. 2015; 54: 5713
17e Pan M. Gao S. Zheng Y. Tan X. Lan H. Tan X. Sun D. Lu L. Wang T. Zheng Q. Huang Y. Wang J. Liu L. J. Am. Chem. Soc. 2016; 138: 7429

18a Luger K. Rechsteiner TJ. Richmond TJ. Methods Mol. Biol 1999; 119: 1
18b Dyer PN. Edayathumangalam RS. White CL. Bao Y. Chakravarthy S. Muthurajan UM. Luger K. Methods Enzymol. 2003; 375: 23

19 Taguchi H. Horikoshi N. Arimura Y. Kurumizaka H. Methods 2014; 70: 119

Supplementary Material

Supporting Information