Literature DB >> 27711380

Genetically encoded fluorophenylalanines enable insights into the recognition of lysine trimethylation by an epigenetic reader.

Yan-Jiun Lee1, M J Schmidt2, Jeffery M Tharp1, Annemarie Weber2, Amber L Koenig3, Hong Zheng4, Jianmin Gao4, Marcey L Waters3, Daniel Summerer5, Wenshe R Liu1.   

Abstract

Fluorophenylalanines bearing 2-5 fluorine atoms at the phenyl ring have been genetically encoded by amber codon. Replacement of F59, a phenylalanine residue that is directly involved in interactions with trimethylated K9 of histone H3, in the Mpp8 chromodomain recombinantly with fluorophenylalanines significantly impairs the binding to a K9-trimethylated H3 peptide.

Entities:  

Year:  2016        PMID： 27711380      PMCID： PMC5072174          DOI： 10.1039/c6cc05959g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  54 in total

1.  The Cationminus signpi Interaction.

Authors:  Jennifer C. Ma; Dennis A. Dougherty
Journal:  Chem Rev       Date:  1997-08-05       Impact factor: 60.622

2.  Fluorinated Coiled-Coil Proteins Prepared In Vivo Display Enhanced Thermal and Chemical Stability This work was supported by a grant from the U.S. Army Research Office. Y. Tang is supported by a Whitaker Graduate Research Fellowship. We thank Dr. Gary Hathaway for performing matrix-assisted laser desorption/ionization analyses.

Authors:  Yi Tang; Giovanna Ghirlanda; Wendy A. Petka; Tadashi Nakajima; William F. DeGrado; David A. Tirrell
Journal:  Angew Chem Int Ed Engl       Date:  2001-04-17       Impact factor: 15.336

3.  Studies on the mechanism of protein synthesis; incorporation of p-fluorophenylalanine into alpha-amylase of Bacillus subtilis.

Authors:  A YOSHIDA
Journal:  Biochim Biophys Acta       Date:  1960-06-17

4.  Stabilization of coiled-coil peptide domains by introduction of trifluoroleucine.

Authors:  Y Tang; G Ghirlanda; N Vaidehi; J Kua; D T Mainz; W A Goddard III; W F DeGrado; D A Tirrell
Journal:  Biochemistry       Date:  2001-03-06       Impact factor: 3.162

5.  MD simulation of the Na+-phenylalanine complex in water: competition between cation-pi interaction and aqueous solvation.

Authors:  Francesca Costanzo; Raffaele Guido Della Valle; Vincenzo Barone
Journal:  J Phys Chem B       Date:  2005-12-08       Impact factor: 2.991

6.  Virtual screening for binding of phenylalanine analogues to phenylalanyl-tRNA synthetase.

Authors:  Pin Wang; Nagarajan Vaidehi; David A Tirrell; William A Goddard
Journal:  J Am Chem Soc       Date:  2002-12-04       Impact factor: 15.419

7.  Idiosyncrasy and identity in the prokaryotic Phe-system: crystal structure of E. coli phenylalanyl-tRNA synthetase complexed with phenylalanine and AMP.

Authors:  Inbal Mermershtain; Igal Finarov; Liron Klipcan; Naama Kessler; Haim Rozenberg; Mark G Safro
Journal:  Protein Sci       Date:  2011-01       Impact factor: 6.725

8.  Approaches to the assignment of (19)F resonances from 3-fluorophenylalanine labeled calmodulin using solution state NMR.

Authors:  Julianne L Kitevski-Leblanc; Ferenc Evanics; R Scott Prosser
Journal:  J Biomol NMR       Date:  2010-04-18       Impact factor: 2.835

9.  Distinct mode of methylated lysine-4 of histone H3 recognition by tandem tudor-like domains of Spindlin1.

Authors:  Na Yang; Weixiang Wang; Yan Wang; Mingzhu Wang; Qiang Zhao; Zihe Rao; Bing Zhu; Rui-Ming Xu
Journal:  Proc Natl Acad Sci U S A       Date:  2012-10-17       Impact factor: 11.205

10.  Structural basis for specific binding of human MPP8 chromodomain to histone H3 methylated at lysine 9.

Authors:  Jing Li; Zhihong Li; Jianbin Ruan; Chao Xu; Yufeng Tong; Patricia W Pan; Wolfram Tempel; Lissete Crombet; Jinrong Min; Jianye Zang
Journal:  PLoS One       Date:  2011-10-12       Impact factor: 3.240
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  9 in total

1.  Engineering aminoacyl-tRNA synthetases for use in synthetic biology.

Authors:  Natalie Krahn; Jeffery M Tharp; Ana Crnković; Dieter Söll
Journal:  Enzymes       Date:  2020-09-08

Review 2.  Cation-π Interactions and their Functional Roles in Membrane Proteins.

Authors:  Daniel T Infield; Ali Rasouli; Grace D Galles; Christophe Chipot; Emad Tajkhorshid; Christopher A Ahern
Journal:  J Mol Biol       Date:  2021-05-04       Impact factor: 5.469

3.  Fluorine-induced polarity increases inhibitory activity of BPTI towards chymotrypsin.

Authors:  Jakob Leppkes; Nicole Dimos; Bernhard Loll; Thomas Hohmann; Michael Dyrks; Ariane Wieseke; Bettina G Keller; Beate Koksch
Journal:  RSC Chem Biol       Date:  2022-05-19

4.  Investigation of Trimethyllysine Binding by the HP1 Chromodomain via Unnatural Amino Acid Mutagenesis.

Authors:  Stefanie A Baril; Amber L Koenig; Mackenzie W Krone; Katherine I Albanese; Cyndi Qixin He; Ga Young Lee; Kendall N Houk; Marcey L Waters; Eric M Brustad
Journal:  J Am Chem Soc       Date:  2017-11-20       Impact factor: 15.419

5.  Discovery of an H3K36me3-Derived Peptidomimetic Ligand with Enhanced Affinity for Plant Homeodomain Finger Protein 1 (PHF1).

Authors:  Isabelle A Engelberg; Jiuyang Liu; Jacqueline L Norris-Drouin; Stephanie H Cholensky; Samantha A Ottavi; Stephen V Frye; Tatiana G Kutateladze; Lindsey I James
Journal:  J Med Chem       Date:  2021-05-17       Impact factor: 8.039

6.  A Designed, Highly Efficient Pyrrolysyl-tRNA Synthetase Mutant Binds o-Chlorophenylalanine Using Two Halogen Bonds.

Authors:  Erol C Vatansever; Kai S Yang; Zhi Zachary Geng; Yuchen Qiao; Pingwei Li; Shiqing Xu; Wenshe Ray Liu
Journal:  J Mol Biol       Date:  2022-03-09       Impact factor: 6.151

Review 7.  Trimethyllysine: From Carnitine Biosynthesis to Epigenetics.

Authors:  Marijn N Maas; Jordi C J Hintzen; Miriam R B Porzberg; Jasmin Mecinović
Journal:  Int J Mol Sci       Date:  2020-12-11       Impact factor: 5.923

8.  Non-Canonical Amino Acid-Based Engineering of (R)-Amine Transaminase.

Authors:  Amol D Pagar; Hyunwoo Jeon; Taresh P Khobragade; Sharad Sarak; Pritam Giri; Seonga Lim; Tae Hyeon Yoo; Byoung Joon Ko; Hyungdon Yun
Journal:  Front Chem       Date:  2022-02-28       Impact factor: 5.221

9.  The Role of Tryptophan in π Interactions in Proteins: An Experimental Approach.

Authors:  Jinfeng Shao; Bastiaan P Kuiper; Andy-Mark W H Thunnissen; Robbert H Cool; Liang Zhou; Chenxi Huang; Bauke W Dijkstra; Jaap Broos
Journal:  J Am Chem Soc       Date:  2022-07-22       Impact factor: 16.383
  9 in total

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