Geranyl modification on the tryptophan residue of ComX RO-E-2 pheromone by a cell-free system

FEBS Letters

Volumn 586, Issue 2, 2012, Pages 174-179

  Tsuji, Fumitada ^a   Ishihara, Ayako ^a   Kurata, Keiko ^a   Nakagawa, Aya ^a   Okada, Masahiro ^b   Kitamura, Shigeyuki ^a   Kanamaru, Kyoko ^a   Masuda, Yuichi ^c   Murakami, Kazuma ^c   Irie, Kazuhiro ^c   Sakagami, Youji ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b CHUBU UNIVERSITY   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

Bacillus subtilis; ComX pheromone; Posttranslational modification; Prenylation; Prenyltransferase; Quorum sensing

Indexed keywords

COMX RO E 2 PHEROMONE; PHEROMONE; TRYPTOPHAN; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BACILLUS SUBTILIS; BACTERIUM MUTANT; CELL FREE SYSTEM; CONTROLLED STUDY; ENZYME MECHANISM; ESCHERICHIA COLI; GERANYLATION; HORMONE DETERMINATION; HORMONE STRUCTURE; IN VITRO STUDY; NONHUMAN; POLYACRYLAMIDE GEL ELECTROPHORESIS; PRIORITY JOURNAL; PROTEIN MODIFICATION; PROTEIN PRENYLATION; PROTEIN PROCESSING; QUORUM SENSING;

AMINO ACID SEQUENCE; BACILLUS SUBTILIS; BACTERIAL PROTEINS; CATALYSIS; CELL-FREE SYSTEM; GERANYLTRANSTRANSFERASE; MODELS, BIOLOGICAL; MOLECULAR SEQUENCE DATA; PHEROMONES; PROTEIN PRENYLATION; PROTEIN PROCESSING, POST-TRANSLATIONAL; TRYPTOPHAN;

BACILLUS SUBTILIS; POSIBACTERIA;

EID: 84855768922     PISSN: 00145793     EISSN: 18733468     Source Type: Journal    
DOI: 10.1016/j.febslet.2011.12.012     Document Type: Article

References (33)

1. W.C. Fuqua, S.C. Winans, and E.P. Greenberg Quorum sensing in bacteria: the LuxR-LuxI family of cell density-responsive transcriptional regulators J. Bacteriol. 176 1994 269 275 (Pubitemid 24034041)
2. O. Johnsborg, V. Eldholm, and L.S. Havarstein Natural genetic transformation: prevalence, mechanisms and function Res. Microbiol. 158 2007 767 778 (Pubitemid 350235180)
3. R. Magnuson, J. Solomon, and A.D. Grossman Biochemical and genetic characterization of a competence pheromone from B. subtilis Cell 77 1994 207 216 (Pubitemid 24138618)
4. M. Okada, I. Sato, S.J. Cho, H. Iwata, T. Nishio, D. Dubnau, and Y. Sakagami Structure of the Bacillus subtilis quorum-sensing peptide pheromone ComX Nat. Chem. Biol. 1 2005 23 24
5. M. Okada, H. Yamaguchi, I. Sato, F. Tsuji, D. Dubnau, and Y. Sakagami Chemical structure of posttranslational modification with a farnesyl group on tryptophan Biosci. Biotechnol. Biochem. 72 2008 914 918 (Pubitemid 351463662)
6. M. Okada, I. Sato, S.J. Cho, Y. Suzuki, M. Ojika, D. Dubnau, and Y. Sakagami Towards structural determination of the ComX pheromone: synthetic studies on peptides containing geranyltryptophan Biosci. Biotechnol. Biochem. 68 2004 2374 2387 (Pubitemid 40033515)
7. M. Okada, I. Sato, S.J. Cho, D. Dubnau, and Y. Sakagami Chemical synthesis of ComX pheromone and related peptides containing isoprenoidal tryptophan residues Tetrahedron 62 2006 8907 8918 (Pubitemid 44176079)
8. M. Okada, H. Yamaguchi, I. Sato, S.J. Cho, D. Dubnau, and Y. Sakagami Structure-activity relationship studies on quorum sensing ComX(RO-E-2) pheromone Bioorg. Med. Chem. Lett. 17 2007 1705 1707 (Pubitemid 46274337)
9. RO-E-2 pheromone biological activity Bioorg. Med. Chem. Lett. 21 2011 4041 4044
10. K. Bacon Schneider, T.M. Palmer, and A.D. Grossman Characterization of comQ and comX, two genes required for production of ComX pheromone in Bacillus subtilis J. Bacteriol. 184 2002 410 419 (Pubitemid 34027380)
11. Y. Weinrauch, T. Msadek, F. Kunst, and D. Dubnau Sequence and properties of comQ, a new competence regulatory gene of Bacillus subtilis J. Bacteriol. 173 1991 5685 5693
12. L.S. Tran, T. Nagai, and Y. Itoh Divergent structure of the ComQXPA quorum-sensing components: molecular basis of strain-specific communication mechanism in Bacillus subtilis Mol. Microbiol. 37 2000 1159 1171
13. S. Takahashi, and T. Koyama Structure and function of cis-prenyl chain elongating enzymes Chem. Rec. 6 2006 194 205 (Pubitemid 44369415)
14. P.J. Casey, and M.C. Seabra Protein prenyltransferases J. Biol. Chem. 271 1996 5289 5292 (Pubitemid 26083855)
15. K.T. Lane, and L.S. Beese Thematic review series: lipid posttranslational modifications. Structural biology of protein farnesyltransferase and geranylgeranyltransferase type I J. Lipid. Res. 47 2006 681 699
16. K.F. Leung, R. Baron, and M.C. Seabra Thematic review series: lipid posttranslational modifications. Geranylgeranylation of Rab GTPases J. Lipid. Res. 47 2006 467 475
17. Y. Kamiya, A. Sakurai, S. Tamura, and N. Takahashi Structure of rhodotorucine A, a novel lipopeptide, inducing mating tube formation in Rhodosporidium toruloides Biochem. Biophys. Res. Commun. 83 1978 1077 1083 (Pubitemid 8402821)
18. Y. Sakagami, A. Isogai, A. Suzuki, S. Tamura, C. Kitada, and M. Fujino Structure of tremerogen A-10, a peptidal hormone inducing conjugation tube formation in Tremella mesenterica Agric. Biol. Chem. 43 1979 2643 2645 (Pubitemid 11248763)
19. Y. Sakagami, M. Yoshida, A. Isogai, and A. Suzuki Peptidal sex hormones inducing conjugation tube formation in compatible mating-type cells of Tremella mesenterica Science 212 1981 1525 1527 (Pubitemid 11063028)
20. S.J. McTaggart Isoprenylated proteins Cell. Mol. Life Sci. 63 2006 255 267 (Pubitemid 43202309)
21. A.D. Basso, P. Kirschmeier, and W.R. Bishop Lipid posttranslational modifications. Farnesyl transferase inhibitors J. Lipid. Res. 47 2006 15 31
22. U.T. Nguyen Analysis of the eukaryotic prenylome by isoprenoid affinity tagging Nat. Chem. Biol. 5 2009 227 235
23. U.T. Nguyen, R.S. Goody, and K. Alexandrov Understanding and exploiting protein prenyltransferases ChemBioChem 11 2010 1194 1201
24. M. Okada, H. Yamaguchi, I. Sato, F. Tsuji, J. Qi, D. Dubnau, and Y. Sakagami Acid labile ComX pheromone from Bacillus mojavensis RO-H-1 Biosci. Biotechnol. Biochem. 71 2007 1807 1810 (Pubitemid 47358713)
25. P. Tortosa, L. Logsdon, B. Kraigher, Y. Itoh, I. Mandic-Mulec, and D. Dubnau Specificity and genetic polymorphism of the Bacillus competence quorum-sensing system J. Bacteriol. 183 2001 451 460 (Pubitemid 32048102)
26. M. Ansaldi, and D. Dubnau Diversifying selection at the Bacillus quorum-sensing locus and determinants of modification specificity during synthesis of the ComX pheromone J. Bacteriol. 186 2004 15 21 (Pubitemid 38020281)
27. M. Ansaldi, D. Marolt, T. Stebe, I. Mandic-Mulec, and D. Dubnau Specific activation of the Bacillus quorum-sensing systems by isoprenylated pheromone variants Mol. Microbiol. 44 2002 1561 1573 (Pubitemid 34639433)
28. K. Irie, K. Oie, A. Nakahara, Y. Yanai, H. Ohigashi, P.A. Wender, H. Fukuda, H. Konishi, and U. Kikkawa Molecular basis for protein kinase C isozyme-selective binding: The synthesis, folding, and phorbol ester binding of the cysteine-rich domains of all protein kinase C isozymes J. Am. Chem. Soc. 120 1998 9159 9167 (Pubitemid 28452689)
29. D. Mori, Y. Kimura, S. Kitamura, Y. Sakagami, Y. Yoshioka, T. Shintani, T. Okamoto, and M. Ojika Spongolactams, farnesyl transferase inhibitors from a marine sponge: isolation through an LC/MS-guided assay, structures, and semisyntheses J. Org. Chem. 72 2007 7190 7198 (Pubitemid 47425486)
30. M.C. Seabra, J.L. Goldstein, T.C. Sudhof, and M.S. Brown Rab geranylgeranyl transferase. A multisubunit enzyme that prenylates GTP-binding proteins terminating in Cys-X-Cys or Cys-Cys J. Biol. Chem. 267 1992 14497 14503
31. J.F. Moomaw, and P.J. Casey Mammalian protein geranylgeranyltransferase. Subunit composition and metal requirements J. Biol. Chem. 267 1992 17438 17443
32. Y. Reiss, M.S. Brown, and J.L. Goldstein Divalent cation and prenyl pyrophosphate specificities of the protein farnesyltransferase from rat brain, a zinc metalloenzyme J. Biol. Chem. 267 1992 6403 6408
33. W.J. Chen, J.F. Moomaw, L. Overton, T.A. Kost, and P.J. Casey High level expression of mammalian protein farnesyltransferase in a baculovirus system. The purified protein contains zinc J. Biol. Chem. 268 1993 9675 9680 (Pubitemid 23146027)