Discovery and assembly-line biosynthesis of the lymphostin pyrroloquinoline alkaloid family of mtor inhibitors in salinispora bacteria

Journal of the American Chemical Society

Volumn 133, Issue 34, 2011, Pages 13311-13313

  Miyanaga, Akimasa ^a   Janso, Jeffrey E ^b   McDonald, Leonard ^b   He, Min ^b   Liu, Hongbo ^b   Barbieri, Laurel ^b   Eustáquio, Alessandra S ^b   Fielding, Elisha N ^a   Carter, Guy T ^b   Jensen, Paul R ^a   Feng, Xidong ^b   Leighton, Margaret ^b   Koehn, Frank E ^b   Moore, Bradley S ^a,c  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^b PFIZER INC   (United States)

^c UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHETIC GENE CLUSTER; GENE MUTATIONS; INHIBITORY ACTIVITY; MOLECULAR BASIS; NATURAL PRODUCTS; NONRIBOSOMAL PEPTIDE; PYRROLOQUINOLINE; STABLE ISOTOPES; SYNTHASES;

AMINO ACIDS; ANTIBIOTICS; BIOCHEMISTRY; BIOSYNTHESIS; GENES; ISOTOPES; KETONES; METABOLITES; NITROGEN COMPOUNDS; POLYPEPTIDES;

ASSEMBLY;

ALKALOID DERIVATIVE; LYMPHOSTIN PYRROLOQUINOLINE ALKALOID FAMILY; LYMPHOSTINOL; MAMMALIAN TARGET OF RAPAMYCIN INHIBITOR; NEOLYMPHOSTIN A; NEOLYMPHOSTIN B; NEOLYMPHOSTIN C; NEOLYMPHOSTIN D; NEOLYMPHOSTINOL A; NEOLYMPHOSTINOL B; NEOLYMPHOSTINOL C; NEOLYMPHOSTINOL D; PEPTIDE SYNTHASE; POLYKETIDE SYNTHASE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; ENZYME INHIBITION; GENE CLUSTER; GENE MUTATION; HYBRID; MARINE BACTERIUM; NONHUMAN; NONRIBOSOMAL PEPTIDE SYNTHESIS; PROTEIN ASSEMBLY; SALINISPORA ARENICOLA; SALINISPORA PACIFICA; SALINISPORA TROPICA;

ACTINOMYCETALES; ALKALOIDS; ENZYME INHIBITORS; PYRROLES; QUINOLINES; TOR SERINE-THREONINE KINASES;

EID: 80052099035     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja205655w     Document Type: Article

References (24)

1. Perry, N. B.; Blunt, J. W.; McCombs, J. D.; Munro, M. H. G. J. Org. Chem. 1986, 51, 5476-5478
2. Antunes, E. M.; Copp, B. R.; Davies-Coleman, M. T.; Samaai, T. Nat. Prod. Rep. 2005, 22, 62-72
3. Sakemi, S.; Sun, H. H.; Jefford, C. W.; Bernardinelli, G. Tetrahedron Lett. 1989, 30, 2517-2520
4. Chang, L. C.; Otero-Quintero, S.; Hooper, J. N. A.; Bewley, C. A. J. Nat. Prod. 2002, 65, 776-778
5. Stierle, D. B.; Faulkner, D. J. J. Nat. Prod. 1991, 54, 1131-1133
6. Schmidt, E. W.; Harper, M. K.; Faulkner, D. J. J. Nat. Prod. 1995, 58, 1861-1867
7. Radisky, D. C.; Radisky, E. S.; Barrows, L. R.; Copp, B. R.; Kramer, R. A.; Ireland, C. M. J. Am. Chem. Soc. 1993, 115, 1632-1638
8. Ishibashi, M.; Iwasaki, T.; Imai, S.; Sakamoto, S.; Yamaguchi, K.; Ito, A. J. Nat. Prod. 2001, 64, 108-110
9. Peters, S.; Spiteller, P. J. Nat. Prod. 2007, 70, 1274-1277
10. Peters, S.; Spiteller, P. Eur. J. Org. Chem. 2007, 1571-1576
11. Hughes, C. C.; MacMillan, J. B.; Gaudêncio, S. P.; Fenical, W.; La Clair, J. J. Angew. Chem., Int. Ed. 2009, 48, 728-732
12. Hughes, C. C.; MacMillan, J. B.; Gaudêncio, S. P.; Jensen, P. R.; Fenical, W. Angew. Chem., Int. Ed. 2009, 48, 725-727
13. Nagata, H.; Ochiai, K.; Aotani, Y.; Ando, K.; Yoshida, M.; Takahashi, I.; Tamaoki, T. J. Antibiot. 1997, 50, 537-542
14. Aotani, Y.; Nagata, H.; Yoshida, M. J. Antibiot. 1997, 50, 543-545
15. Nagata, H.; Yano, H.; Sasaki, K.; Sato, S.; Nakanishi, S.; Takahashi, I.; Tamaoki, T. Biosci., Biotechnol., Biochem. 2002, 66, 501-507
16. Tatsuta, K.; Imamura, K.; Itoh, S.; Kasai, S. Tetrahedron Lett. 2004, 45, 2847-2850
17. Udwary, D. W.; Zeigler, L.; Asolkar, R. N.; Singan, V.; Lapidus, A.; Fenical, W.; Jensen, P. R.; Moore, B. S. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 10376-10381
18. Penn, K.; Jenkins, C.; Nett, M.; Udwary, D. W.; Gontang, E. A.; McGlinchey, R. P.; Foster, B.; Lapidus, A.; Podell, S.; Allen, E. E.; Moore, B. S.; Jensen, P. R. ISME J. 2009, 3, 1193-1203
19. Nett, M.; Ikeda, H.; Moore, B. S. Nat. Prod. Rep. 2009, 26, 1362-1384
20. May, J. J.; Kessler, N.; Marahiel, M. A.; Stubbs, M. T. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 12120-12125
21. Gulder, T. A. M.; Moore, B. S. Angew. Chem., Int. Ed. 2010, 49, 9346-9367
22. Schultz, A. W.; Oh, D.-C.; Carney, J. R.; Williamson, R. T.; Udwary, D. W.; Jensen, P. R.; Gould, S. J.; Fenical, W.; Moore, B. S. J. Am. Chem. Soc. 2008, 130, 4507-4516
23. Eustáquio, A. S.; Pojer, F.; Noel, J. P.; Moore, B. S. Nat. Chem. Biol. 2008, 4, 69-74
24. Du, L.; Lou, L. Nat. Prod. Rep. 2010, 27, 255-278