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Bioscience, Biotechnology, and Biochemistry Volume 72, 2008 - Issue 3
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Original Articles

Chemical Structure of Posttranslational Modification with A Farnesyl Group on Tryptophan

Masahiro OKADAGraduate School of Bioagricultural Sciences, Nagoya University
,
Hisao YAMAGUCHIGraduate School of Bioagricultural Sciences, Nagoya University
,
Isao SATOGraduate School of Bioagricultural Sciences, Nagoya University
,
Fumitada TSUJIGraduate School of Bioagricultural Sciences, Nagoya University
,
David DUBNAUPublic Health Research Institute
&
Youji SAKAGAMIGraduate School of Bioagricultural Sciences, Nagoya University
Pages 914-918 | Received 07 Jan 2008, Accepted 03 Feb 2008, Published online: 22 May 2014

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Kazutake Hirooka, Saki Shioda & Masahiro Okada. (2020) Identification of critical residues for the catalytic activity of ComQ, a Bacillus prenylation enzyme for quorum sensing, by using a simple bioassay system. Bioscience, Biotechnology, and Biochemistry 84:2, pages 347-357.
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Shunsuke Hayashi, Syohei Usami, Yuta Nakamura, Koki Ozaki & Masahiro Okada. (2015) Identification of a quorum sensing pheromone posttranslationally farnesylated at the internal tryptophan residue from Bacillus subtilis subsp. natto. Bioscience, Biotechnology, and Biochemistry 79:10, pages 1567-1569.
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Masahiro Okada, Ayako Ishihara, Risa Yamasaki, Fumitada Tsuji, Shunsuke Hayashi, Syohei Usami & Youji Sakagami. (2014) A region corresponding to second aspartate-rich motif in tryptophan isoprenylating enzyme, ComQ, serves as a substrate-binding site. Bioscience, Biotechnology, and Biochemistry 78:4, pages 550-555.
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Fumitada TSUJI, Ayako ISHIHARA, Aya NAKAGAWA, Masahiro OKADA, Shigeyuki KITAMURA, Kyoko KANAMARU, Yuichi MASUDA, Kazuma MURAKAMI, Kazuhiro IRIE & Youji SAKAGAMI. (2012) Lack of the Consensus Sequence Necessary for Tryptophan Prenylation in the ComX Pheromone Precursor. Bioscience, Biotechnology, and Biochemistry 76:8, pages 1492-1496.
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Masahiro OKADA. (2011) Post-Translational Isoprenylation of Tryptophan. Bioscience, Biotechnology, and Biochemistry 75:8, pages 1413-1417.
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Articles from other publishers (31)

Azusa Miyata, Sohei Ito & Daisuke Fujinami. (2023) Structure Prediction and Genome Mining‐Aided Discovery of the Bacterial C‐Terminal Tryptophan Prenyltransferase PalQ. Advanced Science.
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Chayanid Ongpipattanakul, Emily K. Desormeaux, Adam DiCaprio, Wilfred A. van der Donk, Douglas A. Mitchell & Satish K. Nair. (2022) Mechanism of Action of Ribosomally Synthesized and Post-Translationally Modified Peptides. Chemical Reviews 122:18, pages 14722-14814.
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Chenghai Sun, Wenya Tian, Zhi Lin & Xudong Qu. (2022) Biosynthesis of pyrroloindoline-containing natural products. Natural Product Reports 39:9, pages 1721-1765.
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Sylvie Rebuffat. (2022) Ribosomally synthesized peptides, foreground players in microbial interactions: recent developments and unanswered questions. Natural Product Reports 39:2, pages 273-310.
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Jeffrey D. Rudolf, Tyler A. Alsup, Baofu Xu & Zining Li. (2021) Bacterial terpenome. Natural Product Reports 38:5, pages 905-980.
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Leyla Mohammadkhani & Majid M. Heravi. (2020) Applications of Transition‐Metal‐Catalyzed Asymmetric Allylic Substitution in Total Synthesis of Natural Products: An Update. The Chemical Record 21:1, pages 29-68.
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Masahiro Okada & Shimpei Sumimoto. 2020. Quorum Sensing: Microbial Rules of Life. Quorum Sensing: Microbial Rules of Life 201 217 .
Maho Morita, Yue Hao, Jouni K. Jokela, Debosmita Sardar, Zhenjian Lin, Kaarina Sivonen, Satish K. Nair & Eric W. Schmidt. (2018) Post-Translational Tyrosine Geranylation in Cyanobactin Biosynthesis. Journal of the American Chemical Society 140:19, pages 6044-6048.
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Chaitanya Aggarwal & Michael J. Federle. 2018. Molecular Life Sciences. Molecular Life Sciences 872 884 .
Barry M. Trost, Walter H. Chan & Sushant Malhotra. (2017) Development of the Regiodivergent Asymmetric Prenylation of 3‐Substituted Oxindoles. Chemistry – A European Journal 23:18, pages 4405-4414.
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Masahiro Okada, Tomotoshi Sugita & Ikuro Abe. (2017) Posttranslational isoprenylation of tryptophan in bacteria. Beilstein Journal of Organic Chemistry 13, pages 338-346.
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Adam Skiredj, Mehdi A. Beniddir, Laurent Evanno & Erwan Poupon. (2016) Mimicking the Main Events of the Biosynthesis of Drimentines: Synthesis of Δ8′-Isodrimentine A and Related Compounds. European Journal of Organic Chemistry 2016:17, pages 2954-2958.
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Masahiro Okada, Tomotoshi Sugita, Kohei Akita, Yu Nakashima, Tian Tian, Chang Li, Takahiro Mori & Ikuro Abe. (2016) Stereospecific prenylation of tryptophan by a cyanobacterial post-translational modification enzyme. Organic & Biomolecular Chemistry 14:40, pages 9639-9644.
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Arata Yajima. 2016. 331 355 .
Masahiro Okada, Yuta Nakamura, Shunsuke Hayashi, Koki Ozaki & Syohei Usami. (2015) Chemical structure and biological activity of a quorum sensing pheromone from Bacillus subtilis subsp. natto. Bioorganic & Medicinal Chemistry Letters 25:19, pages 4293-4296.
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Christina N. Krute, Ronan K. Carroll, Frances E. Rivera, Andy Weiss, Ryan M. Young, Andrew Shilling, Mohsen Botlani, Sameer Varma, Bill J. Baker & Lindsey N. Shaw. (2015) The disruption of prenylation leads to pleiotropic rearrangements in cellular behavior in S taphylococcus aureus . Molecular Microbiology 95:5, pages 819-832.
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Matthias D’Hondt, Frederick Verbeke, Sofie Stalmans, Bert Gevaert, Evelien Wynendaele & Bart De Spiegeleer. (2014) Derringer desirability and kinetic plot LC-column comparison approach for MS-compatible lipopeptide analysis. Journal of Pharmaceutical Analysis 4:3, pages 173-182.
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Iztok Dogsa, Kumari Sonal Choudhary, Ziva Marsetic, Sanjarbek Hudaiberdiev, Roberto Vera, S?ndor Pongor & Ines Mandic-Mulec. (2014) ComQXPA Quorum Sensing Systems May Not Be Unique to Bacillus subtilis: A Census in Prokaryotic Genomes. PLoS ONE 9:5, pages e96122.
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Arata Yajima. (2014) Recent progress in the chemistry and chemical biology of microbial signaling molecules: quorum-sensing pheromones and microbial hormones. Tetrahedron Letters 55:17, pages 2773-2780.
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Chaitanya Aggarwal & Michael J. Federle. 2021. Molecular Life Sciences. Molecular Life Sciences 1 14 .
Stuart W. Haynes, Xue Gao, Yi Tang & Christopher T. Walsh. (2013) Complexity Generation in Fungal Peptidyl Alkaloid Biosynthesis: A Two-Enzyme Pathway to the Hexacyclic MDR Export Pump Inhibitor Ardeemin. ACS Chemical Biology 8:4, pages 741-748.
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Natalia Korotkova, Jessica S. Hoff, Devon M. Becker, John Kyle Heggen Quinn, Laura M. Icenogle & Steve L. Moseley. (2012) SpyA is a membrane-bound ADP-ribosyltransferase of Streptococcus pyogenes which modifies a streptococcal peptide, SpyB. Molecular Microbiology 83:5, pages 936-952.
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Fumitada Tsuji, Ayako Ishihara, Keiko Kurata, Aya Nakagawa, Masahiro Okada, Shigeyuki Kitamura, Kyoko Kanamaru, Yuichi Masuda, Kazuma Murakami, Kazuhiro Irie & Youji Sakagami. (2011) Geranyl modification on the tryptophan residue of ComX RO‐E‐2 pheromone by a cell‐free system . FEBS Letters 586:2, pages 174-179.
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Fumitada Tsuji, Ko Kobayashi, Masahiro Okada, Hisao Yamaguchi, Makoto Ojika & Youji Sakagami. (2011) The geranyl-modified tryptophan residue is crucial for ComXRO-E-2 pheromone biological activity. Bioorganic & Medicinal Chemistry Letters 21:13, pages 4041-4044.
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Barry M. Trost, Sushant Malhotra & Walter H. Chan. (2011) Exercising Regiocontrol in Palladium-Catalyzed Asymmetric Prenylations and Geranylation: Unifying Strategy toward Flustramines A and B. Journal of the American Chemical Society 133:19, pages 7328-7331.
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Masahiro Okada, Fumitada Tsuji & Youji Sakagami. 2011. Protein Prenylation PART A. Protein Prenylation PART A 183 194 .
Daniel L?pez & Roberto Kolter. (2010) Extracellular signals that define distinct and coexisting cell fates in Bacillus subtilis . FEMS Microbiology Reviews 34:2, pages 134-149.
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Matthew Thoendel & Alexander R. Horswill. 2010. 91 112 .
Xinyu Liu & Christopher T. Walsh. (2009) Characterization of cyclo -Acetoacetyl- l -Tryptophan Dimethylallyltransferase in Cyclopiazonic Acid Biosynthesis: Substrate Promiscuity and Site Directed Mutagenesis Studies . Biochemistry 48:46, pages 11032-11044.
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Masahiro OKADA, Jianhua QI & Youji SAKAGAMI. (2009) Chemistry of microbial signal compounds. Mycotoxins 59:2, pages 55-66.
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John A. McIntosh, Mohamed S. Donia & Eric W. Schmidt. (2009) Ribosomal peptide natural products: bridging the ribosomal and nonribosomal worlds. Natural Product Reports 26:4, pages 537.
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