Genetic Incorporation of ε-N-2-Hydroxyisobutyryl-lysine into Recombinant Histones

ACS Chemical Biology

Volumn 10, Issue 7, 2015, Pages 1599-1603

  Xiao, Han ^a   Xuan, Weimin ^a   Shao, Sida ^a   Liu, Tao ^a   Schultz, Peter G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID TRANSFER RNA LIGASE; EPSILON N 2 HYDROXYISOBUTYRYL LYSINE; HISTONE H2B; LYSINE DERIVATIVE; TRANSFER RNA; UNCLASSIFIED DRUG; HISTONE; LYSINE; RECOMBINANT PROTEIN;

ARTICLE; BACTERIUM; CRYSTAL STRUCTURE; HUMAN; HUMAN CELL; MAMMAL CELL; NONHUMAN; PRIORITY JOURNAL; PROTEIN PROCESSING; ANALOGS AND DERIVATIVES; ANIMAL; ESCHERICHIA COLI; GENE EXPRESSION; GENETICS; HEK293 CELL LINE; METABOLISM; MOLECULAR MODEL;

MAMMALIA;

AMINO ACYL-TRNA SYNTHETASES; ANIMALS; ESCHERICHIA COLI; GENE EXPRESSION; HEK293 CELLS; HISTONES; HUMANS; LYSINE; MODELS, MOLECULAR; PROTEIN PROCESSING, POST-TRANSLATIONAL; RECOMBINANT PROTEINS;

EID: 84937142071     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb501055h     Document Type: Article

References (31)

1. Grunstein, M. (1997) Histone acetylation in chromatin structure and transcription Nature 389, 349-352
2. Jenuwein, T. and Allis, C. D. (2001) Translating the histone code Science 293, 1074-1080
3. Peterson, C. L. and Laniel, M. A. (2004) Histones and histone modifications Curr. Biol. 14, R546-551
4. Shahbazian, M. D. and Grunstein, M. (2007) Functions of site-specific histone acetylation and deacetylation Annu. Rev. Biochem. 76, 75-100
5. Sterner, D. E. and Berger, S. L. (2000) Acetylation of histones and transcription-related factors Microbiol. Mol. Biol. Rev. 64, 435-459
6. Martin, C. and Zhang, Y. (2007) Mechanisms of epigenetic inheritance Curr. Opin. Cell Biol. 19, 266-272
7. Ruthenburg, A. J., Li, H., Patel, D. J., and Allis, C. D. (2007) Multivalent engagement of chromatin modifications by linked binding modules Nat. Rev. Mol. Cell Biol. 8, 983-994
8. Kouzarides, T. (2007) Chromatin modifications and their function Cell 128, 693-705
9. Wysocka, J., Swigut, T., Milne, T. A., Dou, Y., Zhang, X., Burlingame, A. L., Roeder, R. G., Brivanlou, A. H., and Allis, C. D. (2005) WDR5 associates with histone H3 methylated at K4 and is essential for H3 K4 methylation and vertebrate development Cell 121, 859-872
10. Zeng, L. and Zhou, M. M. (2002) Bromodomain: an acetyl-lysine binding domain FEBS Lett. 513, 124-128
11. Dai, L., Peng, C., Montellier, E., Lu, Z., Chen, Y., Ishii, H., Debernardi, A., Buchou, T., Rousseaux, S., Jin, F., Sabari, B. R., Deng, Z., Allis, C. D., Ren, B., Khochbin, S., and Zhao, Y. (2014) Lysine 2-hydroxyisobutyrylation is a widely distributed active histone mark Nat. Chem. Biol. 10, 365-370
12. Groff, D., Chen, P. R., Peters, F. B., and Schultz, P. G. (2010) A Genetically Encoded epsilon-N-Methyl Lysine in Mammalian Cells Chembiochem 11, 1066-1068
13. Bernardes, G. J. L., Chalker, J. M., Errey, J. C., and Davis, B. G. (2008) Facile conversion of cysteine and alkyl cysteines to dehydroalanine on protein surfaces: Versatile and switchable access to functionalized proteins J. Am. Chem. Soc. 130, 5052
14. Guo, J., Wang, J., Lee, J. S., and Schultz, P. G. (2008) Site-specific incorporation of methyl- and acetyl-lysine analogues into recombinant proteins Angew. Chem., Int. Ed. Engl. 47, 6399-6401
15. Nguyen, D. P., Garcia Alai, M. M., Virdee, S., and Chin, J. W. (2010) Genetically directing varepsilon-N, N-dimethyl-L-lysine in recombinant histones Chem. Biol. 17, 1072-1076
16. Simon, M. D., Chu, F. X., Racki, L. R., de la Cruz, C. C., Burlingame, A. L., Panning, B., Narlikar, G. J., and Shokat, K. M. (2007) The site-specific installation of methyl-lysine analogs into recombinant histones Cell 128, 1003-1012
17. Ai, H. W., Lee, J. W., and Schultz, P. G. (2010) A method to site-specifically introduce methyllysine into proteins in E. coli Chem. Commun. (Cambridge, U. K.) 46, 5506-5508
18. Neumann, H., Peak-Chew, S. Y., and Chin, J. W. (2008) Genetically encoding N(epsilon)-acetyllysine in recombinant proteins Nat. Chem. Biol. 4, 232-234
19. Nguyen, D. P., Garcia Alai, M. M., Kapadnis, P. B., Neumann, H., and Chin, J. W. (2009) Genetically encoding N(epsilon)-methyl-L-lysine in recombinant histones J. Am. Chem. Soc. 131, 14194-14195
20. Kim, C. H., Kang, M., Kim, H. J., Chatterjee, A., and Schultz, P. G. (2012) Site-specific incorporation of epsilon-N-crotonyllysine into histones Angew. Chem., Int. Ed. Engl. 51, 7246-7249
21. Gattner, M. J., Vrabel, M., and Carell, T. (2013) Synthesis of epsilon-N-propionyl-, epsilon-N-butyryl-, and epsilon-N-crotonyl-lysine containing histone H3 using the pyrrolysine system Chem. Commun. (Cambridge, U. K.) 49, 379-381
22. Neumann, H., Hancock, S. M., Buning, R., Routh, A., Chapman, L., Somers, J., Owen-Hughes, T., van Noort, J., Rhodes, D., and Chin, J. W. (2009) A method for genetically installing site-specific acetylation in recombinant histones defines the effects of H3 K56 acetylation Mol. Cell 36, 153-163
23. Kavran, J. M., Gundliapalli, S., O'Donoghue, P., Englert, M., Soell, D., and Steitz, T. A. (2007) Structure of pyrrolysyl-tRNA synthetase, an archaeal enzyme for genetic code innovation Proc. Natl. Acad. Sci. U. S. A. 104, 11268-11273
24. Yanagisawa, T., Ishii, R., Fukunaga, R., Kobayashi, T., Sakamoto, K., and Yokoyama, S. (2008) Multistep engineering of pyrrolysyl-tRNA synthetase to genetically encode N(epsilon)-(o-azidobenzyloxycarbonyl) lysine for site-specific protein modification Chem. Biol. 15, 1187-1197
25. Liu, C. C. and Schultz, P. G. (2010) Adding new chemistries to the genetic code Annu. Rev. Biochem. 79, 413-444
26. Xiao, H., Peters, F. B., Yang, P. Y., Reed, S., Chittuluru, J. R., and Schultz, P. G. (2014) Genetic incorporation of histidine derivatives using an engineered pyrrolysyl-tRNA synthetase ACS Chem. Biol. 9, 1092-1096
27. Matyjaszewski, K. and Xia, J. (2001) Atom transfer radical polymerization Chem. Rev. 101, 2921-2990
28. Peeler, J. C., Woodman, B. F., Averick, S., Miyake-Stoner, S. J., Stokes, A. L., Hess, K. R., Matyjaszewski, K., and Mehl, R. A. (2010) Genetically Encoded Initiator for Polymer Growth from Proteins J. Am. Chem. Soc. 132, 13575-13577
29. Chatterjee, A., Sun, S. B., Furman, J. L., Xiao, H., and Schultz, P. G. (2013) A versatile platform for single- and multiple-unnatural amino acid mutagenesis in Escherichia coli Biochemistry 52, 1828-1837
30. Xiao, H., Chatterjee, A., Choi, S. H., Bajjuri, K. M., Sinha, S. C., and Schultz, P. G. (2013) Genetic incorporation of multiple unnatural amino acids into proteins in mammalian cells Angew. Chem., Int. Ed. Engl. 52, 14080-14083
31. Chatterjee, A., Xiao, H., Bollong, M., Ai, H. W., and Schultz, P. G. (2013) Efficient viral delivery system for unnatural amino acid mutagenesis in mammalian cells Proc. Natl. Acad. Sci. U. S. A. 110, 11803-11808