Site-specific incorporation of ε-N-crotonyllysine into histones.

A novel post-translationally modified amino acid, crotonyllysine (Kcr), was genetically incorporated into proteins in bacterial and mammalian cells using an evolved pyrrolysyl-tRNA/synthetase-tRNA pair. The ability to produce histones with homogenous, site-specific Kcr modifications will be valuable in elucidating the biological role of this recently identified post-translational modification.

[1]  B. G. Davis,et al.  Conversion of cysteine into dehydroalanine enables access to synthetic histones bearing diverse post-translational modifications. , 2012, Angewandte Chemie.

[2]  C. Chatterjee,et al.  Chemical approaches to understand the language of histone modifications. , 2011, ACS chemical biology.

[3]  Bing Li,et al.  Readers of histone modifications , 2011, Cell Research.

[4]  Yixue Li,et al.  Regulation of Cellular Metabolism by Protein Lysine Acetylation , 2010, Science.

[5]  Christopher T. Walsh,et al.  Posttranslationale Proteinmodifikation: die Chemie der Proteomdiversifizierung , 2005 .

[6]  M. Pazin,et al.  Histone H4-K16 Acetylation Controls Chromatin Structure and Protein Interactions , 2006, Science.

[7]  J. Chin,et al.  Genetically encoding N(epsilon)-acetyllysine in recombinant proteins. , 2008, Nature chemical biology.

[8]  Yawen Zhang,et al.  Synthesis of Dye-Labeled Lysine Derivatives , 2000 .

[9]  A. Burlingame,et al.  The Site-Specific Installation of Methyl-Lysine Analogs into Recombinant Histones , 2007, Cell.

[10]  A. Shilatifard,et al.  Histone H4 lysine-16 acetylation regulates cellular lifespan , 2009, Nature.

[11]  J. Wyrick,et al.  Deciphering the Roles of the Histone H2B N-Terminal Domain in Genome-Wide Transcription , 2006, Molecular and Cellular Biology.

[12]  Peter G Schultz,et al.  Probing Protein–Protein Interactions with a Genetically Encoded Photo‐crosslinking Amino Acid , 2011, Chembiochem : a European journal of chemical biology.

[13]  R. Roeder,et al.  Chemically ubiquitylated histone H2B stimulates hDot1L-mediated intranucleosomal methylation , 2008, Nature.

[14]  Christian A. Olsen Acylierung von Lysinen: Erweiterung des Repertoires , 2012 .

[15]  P. Tak,et al.  Histone Deacetylase Inhibitors Suppress Inflammatory Activation of Rheumatoid Arthritis Patient Synovial Macrophages and Tissue , 2010, The Journal of Immunology.

[16]  Danny Reinberg,et al.  Histones: annotating chromatin. , 2009, Annual review of genetics.

[17]  J. Chin,et al.  Genetically encoding N(epsilon)-methyl-L-lysine in recombinant histones. , 2009, Journal of the American Chemical Society.

[18]  P. Schultz,et al.  Site-specific incorporation of methyl- and acetyl-lysine analogues into recombinant proteins. , 2008, Angewandte Chemie.

[19]  N. Korolev,et al.  A direct method for site-specific protein acetylation. , 2011, Angewandte Chemie.

[20]  T. Muir,et al.  Expressed protein ligation: a general method for protein engineering. , 1998, Proceedings of the National Academy of Sciences of the United States of America.

[21]  Ronen Marmorstein,et al.  Site-specific introduction of an acetyl-lysine mimic into peptides and proteins by cysteine alkylation. , 2010, Journal of the American Chemical Society.

[22]  Sylvie Garneau-Tsodikova,et al.  Protein posttranslational modifications: the chemistry of proteome diversifications. , 2005, Angewandte Chemie.

[23]  S. Messner,et al.  Histone ADP-ribosylation in DNA repair, replication and transcription. , 2011, Trends in cell biology.

[24]  Ryohei Ishii,et al.  Multistep engineering of pyrrolysyl-tRNA synthetase to genetically encode N(epsilon)-(o-azidobenzyloxycarbonyl) lysine for site-specific protein modification. , 2008, Chemistry & biology.

[25]  J. Chin,et al.  A Method for Genetically Installing Site-Specific Acetylation in Recombinant Histones Defines the Effects of H3 K56 Acetylation , 2009, Molecular cell.

[26]  P. Marks,et al.  Histone deacetylases and cancer: causes and therapies , 2001, Nature Reviews Cancer.

[27]  L. Thompson,et al.  Therapeutic application of histone deacetylase inhibitors for central nervous system disorders , 2008, Nature Reviews Drug Discovery.

[28]  Satpal Virdee,et al.  Genetically directing ɛ-N, N-dimethyl-L-lysine in recombinant histones. , 2010, Chemistry & biology.

[29]  Zhike Lu,et al.  Identification of 67 Histone Marks and Histone Lysine Crotonylation as a New Type of Histone Modification , 2011, Cell.

[30]  P. Cole,et al.  Chemical probes for histone-modifying enzymes. , 2008, Nature chemical biology.

[31]  P. Schultz,et al.  A method to site-specifically introduce methyllysine into proteins in E. coli. , 2010, Chemical communications.

[32]  Athanassios Giannis,et al.  Epigenetik – ein Epizentrum der Genregulation: Histone und histonmodifizierende Enzyme , 2005 .

[33]  P. Dawson,et al.  Synthesis of native proteins by chemical ligation. , 2000, Annual review of biochemistry.

[34]  C. Olsen,et al.  Expansion of the lysine acylation landscape. , 2012, Angewandte Chemie.

[35]  A. Giannis,et al.  Epigenetics--an epicenter of gene regulation: histones and histone-modifying enzymes. , 2005, Angewandte Chemie.

[36]  R. Roeder,et al.  30 nm chromatin fibre decompaction requires both H4-K16 acetylation and linker histone eviction. , 2008, Journal of molecular biology.