Biosynthesis of phenylnannolone A, a multidrug resistance reversal agent from the halotolerant myxobacterium Nannocystis pusilla B150

ChemBioChem

Volumn 15, Issue 5, 2014, Pages 757-765

  Bouhired, Sarah M ^a   Crüsemann, Max ^b   Almeida, Celso ^a   Weber, Tilmann ^c,d   Piel, Jörn ^e   Schäberle, Till F ^a   König, Gabriele M ^a  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^c UNIVERSITY OF TÜBINGEN   (Germany)

^d Chalmers University of Technology   (Denmark)

^e ETH ZURICH   (Switzerland)

Author keywords

biosynthesis; myxobacteria; Nannocystis pusilla; phenylnannolone A; polyketides

Indexed keywords

CINNAMIC ACID; DAUNORUBICIN; METHYLMALONYL COENZYME A MUTASE; MULTIDRUG RESISTANCE PROTEIN; NATURAL PRODUCT; PANTETHEINE PHOSPHATE; PHENYLNANNOLONE A; PHN1 PROTEIN; PHN2 PROTEIN; POLYKETIDE; POLYKETIDE SYNTHASE; PROPIONYL COENZYME A CARBOXYLASE; UNCLASSIFIED DRUG; BIOLOGICAL PRODUCT; PYRONE DERIVATIVE;

AMINO ACID SEQUENCE; ARTICLE; CANCER CELL; CANCER RESISTANCE; DRUG STRUCTURE; ENZYME ANALYSIS; GENE IDENTIFICATION; MYXOCOCCALES; NANNOCYSTIS PUSILLA; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; SEQUENCE ALIGNMENT; BACTERIAL GENE; BIOSYNTHESIS; CHEMISTRY; DRUG EFFECTS; GENETICS; METABOLISM; MULTIDRUG RESISTANCE; PHYLOGENY;

BIOLOGICAL PRODUCTS; BIOSYNTHETIC PATHWAYS; DRUG RESISTANCE, MULTIPLE; GENES, BACTERIAL; MYXOCOCCALES; PHYLOGENY; PYRONES;

EID: 84896388151     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201300676     Document Type: Article

References (57)

1. M. Nett, G. M. König, Nat. Prod. Rep. 2007, 24, 1245-1261.
2. A. Conlin, M. Fornier, C. Hudis, S. Kar, P. Kirkpatrick, Nat. Rev. Drug Discovery 2007, 6, 953-954.
3. J. Staunton, K. J. Weissman, Nat. Prod. Rep. 2001, 18, 380-416.
4. S. C. Wenzel, R. Müller, Nat. Prod. Rep. 2009, 26, 1385-1407.
5. K. Blin, M. H. Medema, D. Kazempour, M. A. Fischbach, R. Breitling, E. Takano, T. Weber, Nucleic Acids Res. 2013, 41, W 204 -W 212.
6. J. Piel, Nat. Prod. Rep. 2010, 27, 996-1047.
7. B. Ohlendorf, S. Leyers, A. Krick, S. Kehraus, M. Wiese, G. M. König, ChemBioChem 2008, 9, 2997-3003.
8. E. Fox, S. E. Bates, Expert Rev. Anticancer Ther. 2007, 7, 447-459.
9. B. Ohlendorf, PhD thesis, University of Bonn (Germany), http://www.hut-verlag.de/9783899638639.html, 2008.
10. T. Weber, C. Rausch, P. Lopez, I. Hoof, V. Gaykova, D. H. Huson, W. Wohlleben, J. Biotechnol. 2009, 140, 13-17.
11. "antismash/clusean" can be found under https://bitbucket.org/ antismash/clusean, 2012.
12. A. V. Demirev, A. Khanal, N. P. K. Hanh, K. T. Nam, D. H. Nam, J. Microbiol. 2011, 49, 407-412.
13. Y.-M. Zhang, J. Hurlbert, S. W. White, C. O. Rock, J. Biol. Chem. 2006, 281, 17390-17399.
14. S. C. Findlow, C. Winsor, T. J. Simpson, J. Crosby, M. P. Crump, Biochemistry 2003, 42, 8423-8433.
15. G. Yadav, R. S. Gokhale, D. Mohanty, J. Mol. Biol. 2003, 328, 335-363.
16. S. Smith, S.-C. Tsai, Nat. Prod. Rep. 2007, 24, 1041-1072.
17. K. Buntin, H. Irschik, K. J. Weissman, E. Luxenburger, H. Blöcker, R. Müller, Chem. Biol. 2010, 17, 342-356.
18. S. Omura, H. Ikeda, J. Ishikawa, A. Hanamoto, C. Takahashi, M. Shinose, Y. Takahashi, H. Horikawa, H. Nakazawa, T. Osonoe, H. Kikuchi, T. Shiba, Y. Sakaki, M. Hattori, Proc. Natl. Acad. Sci. USA 2001, 98, 12215-12220.
19. K. Wu, L. Chung, W. P. Revill, L. Katz, C. D. Reeves, Gene 2000, 251, 81-90.
20. S.-C. Tsai, B. D. Ames, Methods Enzymol. 2009, 459, 17-47.
21. A. T. Keatinge-Clay, Chem. Biol. 2007, 14, 898-908.
22. P. Caffrey, ChemBioChem 2003, 4, 654-657.
23. N. Gaitatzis, B. Silakowski, B. Kunze, G. Nordsiek, H. Blöcker, G. Höfle, R. Müller, J. Biol. Chem. 2002, 277, 13082-13090.
24. O. Perlova, K. Gerth, O. Kaiser, A. Hans, R. Müller, J. Biotechnol. 2006, 121, 174-191.
25. R. Carvalho, R. Reid, N. Viswanathan, H. Gramajo, B. Julien, Gene 2005, 359, 91-98.
26. S.-C. Tsai, L. J. W. Miercke, J. Krucinski, R. Gokhale, J. C.-H. Chen, P. G. Foster, D. E. Cane, C. Khosla, R. M. Stroud, Proc. Natl. Acad. Sci. USA 2001, 98, 14808-14813.
27. M. Bycroft, K. J. Weissman, J. Staunton, P. F. Leadlay, Eur. J. Biochem. 2000, 267, 520-526.
28. D. A. Moffet, C. Khosla, D. E. Cane, Bioorg. Med. Chem. Lett. 2006, 16, 213-216.
29. B. Julien, Z.-Q. Tian, R. Reid, C. D. Reeves, Chem. Biol. 2006, 13, 1277-1286.
30. H. Liu, K. A. Reynolds, J. Bacteriol. 1999, 181, 6806-6813.
31. T. J. Erb, J. Rétey, G. Fuchs, B. E. Alber, J. Biol. Chem. 2008, 283, 32283-32293.
32. T. J. Erb, G. Fuchs, B. E. Alber, Mol. Microbiol. 2009, 73, 992-1008.
33. S. F. Haydock, A. N. Appleyard, T. Mironenko, J. Lester, N. Scott, P. F. Leadlay, Microbiology 2005, 151, 3161-3169.
34. R. Fouces, E. Mellado, B. Díez, J. L. Barredo, Microbiology 1999, 145, 855-868.
35. J. W. Vrijbloed, K. Zerbe-Burkhardt, A. Ratnatilleke, A. Grubelnik-Leiser, J. A. Robinson, J. Bacteriol. 1999, 181, 5600-5605.
36. Y. A. Chan, A. M. Podevels, B. M. Kevany, M. G. Thomas, Nat. Prod. Rep. 2009, 26, 90-114.
37. L. Diacovich, D. L. Mitchell, H. Pham, G. Gago, M. M. Melgar, C. Khosla, H. Gramajo, S.-C. Tsai, Biochemistry 2004, 43, 14027-14036.
38. C. Li, K. E. Roege, W. L. Kelly, ChemBioChem 2009, 10, 1064-1072.
39. Y. Xiao, S. Li, S. Niu, L. Ma, G. Zhang, H. Zhang, G. Zhang, J. Ju, C. Zhang, J. Am. Chem. Soc. 2011, 133, 1092-1105.
40. A. Arabolaza, M. E. Shillito, T.-W. Lin, L. Diacovich, M. Melgar, H. Pham, D. Amick, H. Gramajo, S.-C. Tsai, Biochemistry 2010, 49, 7367-7376.
41. Y. Kimura, T. Kojyo, I. Kimura, M. Sato, Arch. Microbiol. 1998, 170, 179-184.
42. V. V. Phelan, Y. Du, J. A. McLean, B. O. Bachmann, Chem. Biol. 2009, 16, 473-478.
43. L. M. Hicks, M. C. Moffitt, L. L. Beer, B. S. Moore, N. L. Kelleher, ACS Chem. Biol. 2006, 1, 93-102.
44. D. Meluzzi, W. H. Zheng, M. Hensler, V. Nizet, P. C. Dorrestein, Bioorg. Med. Chem. Lett. 2008, 18, 3107-3111.
45. K. Rinehart, M. Namikoshi, B. Choi, J. Appl. Phycol. 1994, 6, 159-176.
46. M. C. Moffitt, B. A. Neilan, Appl. Environ. Microbiol. 2004, 70, 6353-6362.
47. N. A. Magarvey, Z. Q. Beck, T. Golakoti, Y. Ding, U. Huber, T. K. Hemscheidt, D. Abelson, R. E. Moore, D. H. Sherman, ACS Chem. Biol. 2006, 1, 766-779.
48. L. Xiang, B. S. Moore, J. Biol. Chem. 2002, 277, 32505-32509.
49. J. S. Williams, M. Thomas, D. J. Clarke, Microbiology 2005, 151, 2543-2550.
50. M. C. Moffitt, G. V. Louie, M. E. Bowman, J. Pence, J. P. Noel, B. S. Moore, Biochemistry 2007, 46, 1004-1012.
51. T. Ahrendt, M. Miltenberger, I. Haneburger, F. Kirchner, M. Kronenwerth, A. O. Brachmann, H. Hilbi, H. B. Bode, ChemBioChem 2013, 14, 1415-1418.
52. P. M. Dewick, Medicinal Natural Products: A Biosynthetic Approach, Wiley, Chichester, 2009, p. 116.
53. C. Hertweck, Angew. Chem. Int. Ed. 2009, 48, 4688-4716
54. Angew. Chem. 2009, 121, 4782-4811.
55. J. Sambrook, D. W. Russell, Molecular Cloning: A Laboratory Manual, Cold Spring Harbor Laboratory Press, New York, 2000.
56. A. Dereeper, V. Guignon, G. Blanc, S. Audic, S. Buffet, F. Chevenet, J.-F. Dufayard, S. Guindon, V. Lefort, M. Lescot, J.-M. Claverie, O. Gascuel, Nucleic Acids Res. 2008, 36, W 465 -W 469.
57. A. Dereeper, S. Audic, J.-M. Claverie, G. Blanc, BMC Evol. Biol. 2010, 10, 8.