Targeted Metagenomics: Finding Rare Tryptophan Dimer Natural Products in the Environment

Journal of the American Chemical Society

Volumn 137, Issue 18, 2015, Pages 6044-6052

  Chang, Fang Yuan ^a   Ternei, Melinda A ^a   Calle, Paula Y ^a   Brady, Sean F ^a  

^a ROCKEFELLER UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; DIMERS; ENVIRONMENTAL MICROBIOLOGY; GENE EXPRESSION; SURVEYS;

BIOSYNTHETIC GENE CLUSTER; CHEMICAL EQUATIONS; CHROMOPYRROLIC ACID; ENVIRONMENTAL SAMPLE; HETEROLOGOUS EXPRESSION; METAGENOMIC LIBRARY CONSTRUCTION; PHYLOGENETIC ANALYSIS; SYNTHETIC BIOLOGY;

GENES;

ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; CARBAZOLE DERIVATIVE; DIMER; HYDROXYSPORINE; INDOLE DERIVATIVE; NATURAL PRODUCT; PYRROLINE DERIVATIVE; REDUCTASPORINE; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG; BIOLOGICAL PRODUCT; DNA; ENZYME; ESCHERICHIA COLI PROTEIN; REBD PROTEIN, E COLI; TRYPTOPHAN;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BIOSYNTHESIS; CHROMOPYRROLIC ACID SYNTHASE GENE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DIMERIZATION; DNA EXTRACTION; DNA LIBRARY; DRUG SCREENING; ENVIRONMENT; GENE; GENE CLUSTER; GENE IDENTIFICATION; GENE SEQUENCE; GENE SYNTHESIS; GENETIC ASSOCIATION; GENETIC VARIABILITY; HETEROLOGOUS EXPRESSION; HUMAN; HUMAN CELL; IC50; METAGENOME; METAGENOMICS; MOLECULAR PHYLOGENY; NONHUMAN; NUCLEOTIDE SEQUENCE; PHARMACOGENOMICS; STRUCTURE ACTIVITY RELATION; SYNTHETIC BIOLOGY; CHEMISTRY; GENETICS; METABOLISM;

BIOLOGICAL PRODUCTS; DIMERIZATION; DNA; ENZYMES; ESCHERICHIA COLI PROTEINS; METAGENOMICS; TRYPTOPHAN;

EID: 84929353102     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b01968     Document Type: Article

References (49)

1. Sterner, O. Methods Mol. Biol. 2012, 864, 393
2. Whitman, W. B.; Coleman, D. C.; Wiebe, W. J. Proc. Natl. Acad. Sci. U. S. A. 1998, 95, 6578
3. Scherlach, K.; Hertweck, C. Org. Biomol Chem. 2009, 7, 1753
4. Wilson, M. C.; Piel, J. Chem. Biol. 2013, 20, 636
5. Milshteyn, A.; Schneider, J. S.; Brady, S. F. Chem. Biol. 2014, 21, 1211
6. Sanchez, C.; Mendez, C.; Salas, J. A. Nat. Prod Rep 2006, 23, 1007
7. Nakano, H.; Omura, S. J. Antibiot. 2009, 62, 17
8. Evans, B. E.; Rittle, K. E.; Bock, M. G.; DiPardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S.; Chang, R. S.; Lotti, V. J.; Cerino, D. J.; Chen, T. B.; Kling, P. J.; Kunkel, K. A.; Springer, J. P.; Hirshfield, J. J. Med. Chem. 1988, 31, 2235
9. Ryan, K. S.; Drennan, C. L. Chem. Biol. 2009, 16, 351
10. Alkhalaf, L. M.; Ryan, K. S. Chem. Biol. 2015, 22, 317
11. Chang, F. Y.; Ternei, M. A.; Calle, P. Y.; Brady, S. F. J. Am. Chem. Soc. 2013, 135, 17906
12. Chang, F. Y.; Brady, S. F. Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 2478
13. Onaka, H.; Taniguchi, S.; Igarashi, Y.; Furumai, T. J. Antibiot. 2002, 55, 1063
14. Sanchez, C.; Butovich, I. A.; Brana, A. F.; Rohr, J.; Mendez, C.; Salas, J. A. Chem. Biol. 2002, 9, 519
15. Pemberton, J. M.; Vincent, K. M.; Penfold, R. J. Curr. Microbiol. 1991, 22, 355
16. Chang, F. Y.; Brady, S. F. J. Am. Chem. Soc. 2011, 133, 9996
17. Chang, F. Y.; Brady, S. F. ChemBioChem 2014, 15, 815
18. Charlop-Powers, Z.; Owen, J. G.; Reddy, B. V.; Ternei, M. A.; Brady, S. F. Proc. Natl. Acad. Sci. U. S. A. 2014, 111, 3757
19. Banik, J. J.; Brady, S. F. Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 17273
20. Brady, S. F. Nat. Protoc. 2007, 2, 1297
21. Howard-Jones, A. R.; Walsh, C. T. Biochemistry 2005, 44, 15652
22. Nishizawa, T.; Gruschow, S.; Jayamaha, D. H.; Nishizawa-Harada, C.; Sherman, D. H. J. Am. Chem. Soc. 2006, 128, 724
23. Howard-Jones, A. R.; Walsh, C. T. J. Am. Chem. Soc. 2007, 129, 11016
24. Groom, K.; Bhattacharya, A.; Zechel, D. L. ChemBioChem 2011, 12, 396
25. Sanchez, C.; Zhu, L.; Brana, A. F.; Salas, A. P.; Rohr, J.; Mendez, C.; Salas, J. A. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 461
26. Salas, A. P.; Zhu, L.; Sanchez, C.; Brana, A. F.; Rohr, J.; Mendez, C.; Salas, J. A. Mol. Microbiol. 2005, 58, 17
27. Kleinschroth, J.; Hartenstein, J.; C., S.; Rudolph, C.; Marme, D.; Paetzold, S. Use of indolocarbazoles for treatment of AIDS and other disorders. DE 4217963 A1 19931202, 1993.
28. Yamada, R.; Hayashi, Y. Preparation of indolocarbazole derivatives as antitumor agents. JP 05140168 A 19930608, 1993.
29. Arakawa, K.; Kodama, K.; Tatsuno, S.; Ide, S.; Kinashi, H. Antimicrob. Agents Chemother. 2006, 50, 1946
30. Cupp-Vickery, J.; Anderson, R.; Hatziris, Z. Proc. Natl. Acad. Sci. U. S. A. 2000, 97, 3050
31. Chiu, H. T.; Chen, Y. L.; Chen, C. Y.; Jin, C.; Lee, M. N.; Lin, Y. C. Mol. BioSyst. 2009, 5, 1180
32. Chiu, H. T.; Lin, Y. C.; Lee, M. N.; Chen, Y. L.; Wang, M. S.; Lai, C. C. Mol. BioSyst. 2009, 5, 1192
33. Sohlenkamp, C.; Lopez-Lara, I. M.; Geiger, O. Prog. Lipid Res. 2003, 42, 115
34. Fougere, F.; Lerudulier, D. J. Gen. Microbiol. 1990, 136, 2503
35. Yin, J.; Zhang, Z. W.; Yu, W. J.; Liao, J. Y.; Luo, X. G.; Shen, Y. J. Am. J. Chin Med. 2010, 38, 157
36. Ueda, J. Y.; Takagi, M.; Shin-ya, K. J. Nat. Prod. 2009, 72, 2181
37. Roll, D. M.; Ireland, C. M.; Lu, H. S. M.; Clardy, J. J. Org. Chem. 1988, 53, 3276
38. Rodriguez-Mata, M.; Frank, A.; Wells, E.; Leipold, F.; Turner, N. J.; Hart, S.; Turkenburg, J. P.; Grogan, G. ChemBioChem 2013, 14, 1372
39. Goldman, P. J.; Ryan, K. S.; Hamill, M. J.; Howard-Jones, A. R.; Walsh, C. T.; Elliott, S. J.; Drennan, C. L. Chem. Biol. 2012, 19, 855
40. Sancelme, M.; Fabre, S.; Prudhomme, M. J. Antibiot. 1994, 47, 792
41. Sanchez-Martinez, C.; Shih, C.; Zhu, G.; Li, T.; Brooks, H. B.; Patel, B. K.; Schultz, R. M.; DeHahn, T. B.; Spencer, C. D.; Watkins, S. A.; Ogg, C. A.; Considine, E.; Dempsey, J. A.; Zhang, F. Bioorg. Med. Chem. Lett. 2003, 13, 3841
42. Ghannoum, M. A.; Rice, L. B. Clin. Microbiol. Rev. 1999, 12, 501
43. Bailly, C.; Qu, X.; Anizon, F.; Prudhomme, M.; Riou, J. F.; Chaires, J. B. Mol. Pharmacol. 1999, 55, 377
44. Prade, L.; Engh, R. A.; Girod, A.; Kinzel, V.; Huber, R.; Bossemeyer, D. Structure 1997, 5, 1627
45. Komander, D.; Kular, G. S.; Schuttelkopf, A. W.; Deak, M.; Prakash, K. R. C.; Bain, J.; Elliott, M.; Garrido-Franco, M.; Kozikowski, A. P.; Alessi, D. R.; Van Aalten, D. M. F. Structure 2004, 12, 215
46. Staker, B. L.; Feese, M. D.; Cushman, M.; Pommier, Y.; Zembower, D.; Stewart, L.; Burgin, A. B. J. Med. Chem. 2005, 48, 2336
47. Kieser, T.; Bibb, M. J.; Buttner, M. J.; Chater, K. F.; Hopwood, D. A. Practical streptomyces genetics; John Innes Foundation: Norwich, UK, 2000.
48. Yasuzawa, T.; Iida, T.; Yoshida, M.; Hirayama, N.; Takahashi, M.; Shirahata, K.; Sano, H. J. Antibiot. 1986, 39, 1072
49. Zivadinovic, D.; Gametchu, B.; Watson, C. S. Breast Cancer Res. 2005, 7, R101