Integration of Chemical, Genetic, and Bioinformatic Approaches Delineates Fungal Polyketide-Peptide Hybrid Biosynthesis

Organic Letters

Volumn 19, Issue 8, 2017, Pages 2002-2005

  Yokoyama, Mamoru ^a   Hirayama, Yuichiro ^a   Yamamoto, Tsuyoshi ^a   Kishimoto, Shinji ^a   Tsunematsu, Yuta ^a   Watanabe, Kenji ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; PEPTIDE; POLYKETIDE; PYRONE DERIVATIVE;

ASPERGILLUS NIDULANS; ASPERGILLUS NIGER; BIOLOGY; BIOSYNTHESIS; CHEMISTRY; FUNGAL GENE; GENETICS; ISOLATION AND PURIFICATION; METABOLISM; MULTIGENE FAMILY; SECONDARY METABOLISM;

ASPERGILLUS NIDULANS; ASPERGILLUS NIGER; BIOLOGICAL PRODUCTS; BIOSYNTHETIC PATHWAYS; COMPUTATIONAL BIOLOGY; GENES, FUNGAL; MULTIGENE FAMILY; PEPTIDES; POLYKETIDES; PYRONES; SECONDARY METABOLISM;

EID: 85018462166     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.7b00559     Document Type: Article

References (24)

1. Brakhage, A. A.; Schroeckh, V. Fungal Genet. Biol. 2011, 48, 15 10.1016/j.fgb.2010.04.004
2. Kato, H.; Tsunematsu, Y.; Yamamoto, T.; Namiki, T.; Kishimoto, S.; Noguchi, H.; Watanabe, K. J. Antibiot. 2016, 69, 561 10.1038/ja.2016.54
3. Scherlach, K.; Boettger, D.; Remme, N.; Hertweck, C. Nat. Prod. Rep. 2010, 27, 869 10.1039/b903913a
4. Schümann, J.; Hertweck, C. J. Am. Chem. Soc. 2007, 129, 9564 10.1021/ja072884t
5. Ishiuchi, K.; Nakazawa, T.; Yagishita, F.; Mino, T.; Noguchi, H.; Hotta, K.; Watanabe, K. J. Am. Chem. Soc. 2013, 135, 7371 10.1021/ja402828w
6. Sato, M.; Yagishita, F.; Mino, T.; Uchiyama, N.; Patel, A.; Chooi, Y. H.; Goda, Y.; Xu, W.; Noguchi, H.; Yamamoto, T.; Hotta, K.; Houk, K. N.; Tang, Y.; Watanabe, K. ChemBioChem 2015, 16, 2294 10.1002/cbic.201500386
7. Wiemann, P.; Guo, C. J.; Palmer, J. M.; Sekonyela, R.; Wang, C. C.; Keller, N. P. Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 17065 10.1073/pnas.1313258110
8. Tsunematsu, Y.; Fukutomi, M.; Saruwatari, T.; Noguchi, H.; Hotta, K.; Tang, Y.; Watanabe, K. Angew. Chem., Int. Ed. 2014, 53, 8475 10.1002/anie.201404804
9. Yamamoto, T.; Tsunematsu, Y.; Hara, K.; Suzuki, T.; Kishimoto, S.; Kawagishi, H.; Noguchi, H.; Hashimoto, H.; Tang, Y.; Hotta, K.; Watanabe, K. Angew. Chem., Int. Ed. 2016, 55, 6207 10.1002/anie.201600940
10. Lazarus, C. M.; Williams, K.; Bailey, A. M. Nat. Prod. Rep. 2014, 31, 1339 10.1039/C4NP00084F
11. Yamamoto, T.; Tsunematsu, Y.; Noguchi, H.; Hotta, K.; Watanabe, K. Org. Lett. 2015, 17, 4992 10.1021/acs.orglett.5b02435
12. Nayak, T.; Szewczyk, E.; Oakley, C. E.; Osmani, A.; Ukil, L.; Murray, S. L.; Hynes, M. J.; Osmani, S. A.; Oakley, B. R. Genetics 2005, 172, 1557 10.1534/genetics.105.052563
13. Ganzlin, M.; Rinas, U. J. Biotechnol. 2008, 135, 266 10.1016/j.jbiotec.2008.04.005
14. Fujii, K.; Ikai, Y.; Oka, H.; Suzuki, M.; Harada, K. Anal. Chem. 1997, 69, 5146 10.1021/ac970289b
15. Abraham, W.-R.; Meyer, H.; Abate, D. Tetrahedron 1995, 51, 4947 10.1016/0040-4020(95)98692-B
16. Tsunematsu, Y.; Ishikawa, N.; Wakana, D.; Goda, Y.; Noguchi, H.; Moriya, H.; Hotta, K.; Watanabe, K. Nat. Chem. Biol. 2013, 9, 818 10.1038/nchembio.1366
17. Riko, R.; Nakamura, H.; Shindo, K. J. Antibiot. 2014, 67, 179 10.1038/ja.2013.91
18. Johnson, M.; Zaretskaya, I.; Raytselis, Y.; Merezhuk, Y.; McGinnis, S.; Madden, T. L. Nucleic Acids Res. 2008, 36, W5 10.1093/nar/gkn201
19. Awakawa, T.; Yang, X. L.; Wakimoto, T.; Abe, I. ChemBioChem 2013, 14, 2095 10.1002/cbic.201300430
20. Abraham, W.-R.; Hanssen, H.-P.; Arfmann, H.-A. Phytochemistry 1995, 38, 843 10.1016/0031-9422(94)00776-P
21. Sandmeier, P.; Tamm, C. Helv. Chim. Acta 1989, 72, 784 10.1002/hlca.19890720419
22. Masi, M.; Meyer, S.; Cimmino, A.; Clement, S.; Black, B.; Evidente, A. J. Agric. Food Chem. 2014, 62, 10304 10.1021/jf5035515
23. Maloney, K. N.; Hao, W.; Xu, J.; Gibbons, J.; Hucul, J.; Roll, D.; Brady, S. F.; Schroeder, F. C.; Clardy, J. Org. Lett. 2006, 8, 4067 10.1021/ol061556f
24. Li, C. S.; Ding, Y.; Yang, B. J.; Miklossy, G.; Yin, H. Q.; Walker, L. A.; Turkson, J.; Cao, S. Org. Lett. 2015, 17, 3556 10.1021/acs.orglett.5b01650