Convergent Total Synthesis of Histone H2B Protein with Site-Specific Ubiquitination at Lys120

Yun-Kun Qi; Qiao-Qiao He; Hua-Song Ai; Jia-Bin Li; Ji-Shen Zheng

doi:10.1055/s-0036-1590794

Synlett, Table of Contents

Synlett 2017; 28(15): 1907-1912
DOI: 10.1055/s-0036-1590794

cluster

Convergent Total Synthesis of Histone H2B Protein with Site-Specific Ubiquitination at Lys120

Yun-Kun Qi

School of Life Sciences, University of Science and Technology of China, Hefei 230027, P. R. of China, Email: lijiabin@ustc.edu.cn Email: jszheng@ustc.edu.cn

,

Qiao-Qiao He

School of Life Sciences, University of Science and Technology of China, Hefei 230027, P. R. of China, Email: lijiabin@ustc.edu.cn Email: jszheng@ustc.edu.cn

,

Hua-Song Ai

School of Life Sciences, University of Science and Technology of China, Hefei 230027, P. R. of China, Email: lijiabin@ustc.edu.cn Email: jszheng@ustc.edu.cn

,

Jia-Bin Li*

School of Life Sciences, University of Science and Technology of China, Hefei 230027, P. R. of China, Email: lijiabin@ustc.edu.cn Email: jszheng@ustc.edu.cn

,

Ji-Shen Zheng *

School of Life Sciences, University of Science and Technology of China, Hefei 230027, P. R. of China, Email: lijiabin@ustc.edu.cn Email: jszheng@ustc.edu.cn

› Author Affiliations

Abstract

All articles of this category

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

Abstract

Histone H2B Lys120 mono-ubiquitylation (H2BK120Ub) plays an important role in regulating gene expression and diverse nuclear processes. For biochemical and biophysical studies of this dynamic post-translational modification, access to homogeneous and workable amount of H2BK120Ub is obligatory. Here we report a new strategy for the convergent total chemical synthesis of homogenous histone H2BK120Ub on multi-milligram scale through the combination of hydrazide-based native chemical ligation and acid-cleavable auxiliary-mediated ligation of peptide hydrazides. The synthetic H2BK120Ub could be efficiently incorporated into nucleosomes, which may provide valuable materials for the biochemical and structural studies of nucleosome complexes involving H2BK120Ub.

Key words

native chemical ligation - chemical synthesis - histone modification - ubiquitination - H2B - H2BK120

Full Text

References

References and Notes
1 Luger K. Mader AW. Richmond RK. Sargent DF. Richmond TJ. Nature (London) 1997; 389: 251
2 Huang H. Lin S. Garcia BA. Zhao Y. Chem. Rev. 2015; 115: 2376

3a Tessarz P. Kouzarides T. Nat. Rev. Mol. Cell Biol. 2014; 15: 703
3b Muller MM. Muir TW. Chem. Rev. 2015; 115: 2296
3c Bowman GD. Poirier MG. Chem. Rev. 2015; 115: 2274

4a Debelouchina GT. Gerecht K. Muir TW. Nat. Chem. Biol. 2017; 13: 105
4b Wilson MD. Benlekbir S. Fradet-Turcotte A. Sherker A. Julien JP. McEwan A. Noordermeer SM. Sicheri F. Rubinstein JL. Durocher D. Nature (London) 2016; 536: 100
4c Fuchs G. Oren M. Biochim. Biophys. Acta 2014; 1839: 694

5a McGinty RK. Kim J. Chatterjee C. Roeder RG. Muir TW. Nature (London) 2008; 453: 812
5b Weake VM. Workman JL. Mol. Cell 2008; 29: 653
5c Kim J. Guermah M. McGinty RK. Lee J. Tang Z. Milne TA. Shilatifard A. Muir TW. Roeder RG. Cell 2009; 137: 459
5d Gopinath P. Ohayon S. Nawatha M. Brik A. Chem. Soc. Rev. 2016; 45: 4171
5e Sun ZW. Allis CD. Nature (London) 2002; 418: 104

6a Mali SM. Singh SK. Eid E. Brik A. J. Am. Chem. Soc. 2017; 139: 4971
6b Nguyen UT. Bittova L. Muller MM. Fierz B. David Y. Houck-Loomis B. Feng V. Dann GP. Muir TW. Nat. Methods 2014; 11: 834
6c David Y. Vila-Perello M. Verma S. Muir TW. Nat. Chem. 2015; 7: 394

7a Holt M. Muir T. Annu. Rev. Biochem. 2015; 84: 265
7b Howard CJ. Yu RR. Gardner ML. Shimko JC. Ottesen JJ. Top. Curr. Chem. 2015; 363: 193
7c Bondalapati S. Jbara M. Brik A. Nat. Chem. 2016; 8: 407
7d Maity SK. Jbara M. Brik A. J. Pept. Sci. 2016; 22: 252
7e Yang R. Liu CF. Top. Curr. Chem. 2015; 362: 89
7f Yu RR. Mahto SK. Justus K. Alexander MM. Howard CJ. Ottesen JJ. Org. Biomol. Chem. 2016; 14: 2603

8a Chatterjee C. McGinty RK. Pellois JP. Muir TW. Angew. Chem. Int. Ed. 2007; 46: 2814
8b McGinty RK. Kohn M. Chatterjee C. Chiang KP. Pratt MR. Muir TW. ACS Chem. Biol. 2009; 4: 958
8c Fierz B. Kilic S. Hieb AR. Luger K. Muir TW. J. Am. Chem. Soc. 2012; 134: 19548

9a Ajish Kumar KS. Haj-Yahya M. Olschewski D. Lashuel HA. Brik A. Angew. Chem. Int. Ed. 2009; 48: 8090
9b Seenaiah M. Jbara M. Mali SM. Brik A. Angew. Chem. Int. Ed. 2015; 54: 12374

10a Yang R. Pasunooti KK. Li F. Liu XW. Liu CF. J. Am. Chem. Soc. 2009; 131: 13592
10b El Oualid F. Merkx R. Ekkebus R. Hameed DS. Smit JJ. de Jong A. Hilkmann H. Sixma TK. Ovaa H. Angew. Chem. Int. Ed. 2010; 49: 10149
10c Merkx R. de Bruin G. Kruithof A. van den Bergh T. Snip E. Lutz M. El Oualid F. Ovaa H. Chem. Sci. 2013; 4: 4494

11a Kumar KS. Spasser L. Ohayon S. Erlich LA. Brik A. Bioconjug. Chem. 2011; 22: 137
11b Haj-Yahya M. Eltarteer N. Ohayon S. Shema E. Kotler E. Oren M. Brik A. Angew. Chem. Int. Ed. 2012; 51: 11535
11c Jbara M. Maity SK. Morgan M. Wolberger C. Brik A. Angew. Chem. Int. Ed. 2016; 55: 4972

12a Chatterjee C. McGinty RK. Fierz B. Muir TW. Nat. Chem. Biol. 2010; 6: 267
12b Fierz B. Chatterjee C. McGinty RK. Bar-Dagan M. Raleigh DP. Muir TW. Nat. Chem. Biol. 2011; 7: 113
12c Holt MT. David Y. Pollock S. Tang Z. Jeon J. Kim J. Roeder RG. Muir TW. Proc. Natl. Acad. Sci. USA 2015; 112: 10365
12d Zhou L. Holt MT. Ohashi N. Zhao A. Muller MM. Wang B. Muir TW. Nat. Commun. 2016; 7: 10589

13a Morgan MT. Haj-Yahya M. Ringel AE. Bandi P. Brik A. Wolberger C. Science 2016; 351: 725
13b Long L. Furgason M. Yao T. Methods 2014; 70: 134

14 Machida S. Sekine S. Nishiyama Y. Horikoshi N. Kurumizaka H. Open. Biol. 2016; 6: 160090
15 Fradet-Turcotte A. Canny MD. Escribano-Diaz C. Orthwein A. Leung CC. Huang H. Landry MC. Kitevski-LeBlanc J. Noordermeer SM. Sicheri F. Durocher D. Nature (London) 2013; 499: 50
16 Bi X. Yang R. Feng X. Rhodes D. Liu CF. Org. Biomol. Chem. 2016; 14: 835

17a Siman P. Karthikeyan SV. Nikolov M. Fischle W. Brik A. Angew. Chem. Int. Ed. 2013; 52: 8059
17b Li J. He Q. Liu Y. Liu S. Tang S. Li C. Sun D. Li X. Zhou M. Zhu P. Bi G. Zhou Z. Zheng JS. Tian C. ChemBioChem 2017; 18: 176
17c Jbara M. Maity SK. Seenaiah M. Brik A. J. Am. Chem. Soc. 2016; 138: 5069
17d He QQ. Qi YK. Liu C. Li JB. Hu HG. Synlett 2017;

18 Qi YK. He QQ. Ai HS. Guo J. Li JB. Chem. Commun. 2017; 53: 4148

19a Fang GM. Li YM. Shen F. Huang YC. Li JB. Lin Y. Cui HK. Liu L. Angew. Chem. Int. Ed. 2011; 50: 7645
19b Fang G.-M. Wang J.-X. Liu L. Angew. Chem. Int. Ed. 2012; 51: 10347
19c Zheng JS. Tang S. Qi YK. Wang ZP. Liu L. Nat. Protoc. 2013; 8: 2483
19d 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
19e Tang S. Si YY. Wang ZP. Mei KR. Chen X. Cheng JY. Zheng JS. Liu L. Angew. Chem. Int. Ed. 2015; 54: 5713
19f Zheng JS. He Y. Zuo C. Cai XY. Tang S. Wang ZA. Zhang LH. Tian CL. Liu L. J. Am. Chem. Soc. 2016; 138: 3553
19g Qi YK. Chang HN. Pan KM. Tian CL. Zheng JS. Chem. Commun. 2015; 51: 14632
19h Dawson PE. Muir TW. Clark-Lewis I. Kent SB. H. Science 1994; 266: 776

20a Botti P. Carrasco MR. Kent SB. H. Tetrahedron Lett. 2001; 42: 1831
20b Macmillan D. Anderson DW. Org. Lett. 2004; 6: 4659
20c Weller CE. Huang W. Chatterjee C. ChemBioChem 2014; 15: 1263
20d Yang R. Bi X. Li F. Cao Y. Liu CF. Chem. Commun. 2014; 50: 7971
20e Loibl SF. Harpaz Z. Seitz O. Angew. Chem. Int. Ed. 2015; 54: 15055
20f 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
20g Gao S. Pan M. Zheng Y. Huang Y. Zheng Q. Sun D. Lu L. Tan X. Tan X. Lan H. Wang J. Wang T. Wang J. Liu L. J. Am. Chem. Soc. 2016; 138: 14497

21 Wan Q. Danishefsky SJ. Angew. Chem. Int. Ed. 2007; 46: 9248

22a Pentelute BL. Kent SB. H. Org. Lett. 2007; 9: 687
22b Maity SK. Jbara M. Laps S. Brik A. Angew. Chem. Int. Ed. 2016; 55: 8108

23a Lowary PT. Widom J. J. Mol. Biol. 1998; 276: 19
23b Dyer PN. Edayathumangalam RS. White CL. Bao Y. Chakravarthy S. Muthurajan UM. Luger K. Methods Enzymol. 2004; 375: 23

Supplementary Material

Supporting Information