Biosynthesis of Long-Chain N-Acyl Amide by a Truncated Polyketide Synthase-Nonribosomal Peptide Synthetase Hybrid Megasynthase in Fungi

Journal of the American Chemical Society

Volumn 140, Issue 4, 2018, Pages 1271-1274

  Hai, Yang ^a   Tang, Yi ^a,b  

^a Engineering IV   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; AMINO ACIDS; BIOCHEMISTRY; FUNGI; KETONES; PEPTIDES;

ACTIVE SITE; BIOINFORMATICS ANALYSIS; GENOME MINING; LONG CHAINS; NONRIBOSOMAL PEPTIDE SYNTHETASES; POLYKETIDE SYNTHASES; POLYKETIDES; SIGNALING LIPIDS;

CHAINS;

5 AMINOVALERIC ACID; G PROTEIN COUPLED RECEPTOR; HISTIDINE; N ACYLAMINO ACID; NONRIBOSOMAL PEPTIDE SYNTHETASE; POLYKETIDE; POLYKETIDE SYNTHASE; POLYKETIDE SYNTHASE NONRIBOSOMAL PEPTIDE SYNTHETASE MEGASYNTHASE; UNCLASSIFIED DRUG; AMIDE; PEPTIDE SYNTHASE;

AMIDATION; AMINO ACID SUBSTITUTION; ARTICLE; BIOINFORMATICS; BIOSYNTHESIS; CARBOXY TERMINAL SEQUENCE; CATALYSIS; ENZYME RELEASE; FUNGUS; PROTEIN DOMAIN; PROTEIN MOTIF; PROTEIN PROTEIN INTERACTION; TALAROMYCES WORTMANII; CHEMISTRY; CONFORMATION; ENZYMOLOGY; METABOLISM; TALAROMYCES;

AMIDES; MOLECULAR CONFORMATION; PEPTIDE SYNTHASES; POLYKETIDE SYNTHASES; TALAROMYCES;

EID: 85041474743     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.7b13350     Document Type: Article

References (26)

1. Cox, R. J. Org. Biomol. Chem. 2007, 5, 2010 10.1039/b704420h
2. Chooi, Y.-H.; Tang, Y. J. Org. Chem. 2012, 77, 9933 10.1021/jo301592k
3. Roberts, D. M.; Bartel, C.; Scott, A.; Ivison, D.; Simpson, T. J.; Cox, R. J. Chem. Sci. 2017, 8, 1116 10.1039/C6SC03496A
4. Cacho, R. A.; Thuss, J.; Xu, W.; Sanichar, R.; Gao, Z.; Nguyen, A.; Vederas, J. C.; Tang, Y. J. Am. Chem. Soc. 2015, 137, 15688 10.1021/jacs.5b11814
5. Boettger, D.; Hertweck, C. ChemBioChem 2013, 14, 28-42 10.1002/cbic.201200624
6. Fisch, K. M.; Bakeer, W.; Yakasai, A. A.; Song, Z.; Pedrick, J.; Wasil, Z.; Bailey, A. M.; Lazarus, C. M.; Simpson, T. J.; Cox, R. J. J. Am. Chem. Soc. 2011, 133, 16635 10.1021/ja206914q
7. Li, X.-W.; Ear, A.; Nay, B. Nat. Prod. Rep. 2013, 30, 765 10.1039/c3np70016j
8. Ma, S. M.; Li, J. W.-H.; Choi, J. W.; Zhou, H.; Lee, K. K. M.; Moorthie, V. A.; Xie, X.; Kealey, J. T.; Da Silva, N. A.; Vederas, J. C.; Tang, Y. Science 2009, 326, 589 10.1126/science.1175602
9. Kakule, T. B.; Lin, Z.; Schmidt, E. W. J. Am. Chem. Soc. 2014, 136, 17882 10.1021/ja511087p
10. Boettger, D.; Bergmann, H.; Kuehn, B.; Shelest, E.; Hertweck, C. ChemBioChem 2012, 13, 2363 10.1002/cbic.201200449
11. Except cyclization domain (Cy) in bacterial NRPSs.
12. Bloudoff, K.; Schmeing, T. M. Biochim. Biophys. Acta, Proteins Proteomics 2017, 1865, 1587 10.1016/j.bbapap.2017.05.010
13. Hillson, N. J.; Balibar, C. J.; Walsh, C. T. Biochemistry 2004, 43, 11344-51 10.1021/bi0489199
14. Haslinger, K.; Peschke, M.; Brieke, C.; Maximowitsch, E.; Cryle, M. J. Nature 2015, 521, 105 10.1038/nature14141
15. According to the Metacyc database: superpathway of l -lysine degradation. Caspi, R.; Altman, T.; Billington, R.; Dreher, K.; Foerster, H.; Fulcher, C. A.; Holland, T. A.; Keseler, I. M.; Kothari, A.; Kubo, A.; Krummenacker, M.; Latendresse, M.; Mueller, L. A.; Ong, Q.; Paley, S.; Subhraveti, P.; Weaver, D. S.; Weerasinghe, D.; Zhang, P.; Karp, P. D. Nucleic Acids Res. 2014, 42, D459 10.1093/nar/gkt1103
16. Mootz, H. D.; Schörgendorfer, K.; Marahiel, M. A. FEMS Microbiol. Lett. 2002, 213, 51 10.1111/j.1574-6968.2002.tb11285.x
17. Liu, X.; Walsh, C. T. Biochemistry 2009, 48, 8746 10.1021/bi901123r
18. Gao, X.; Haynes, S. W.; Ames, B. D.; Wang, P.; Vien, L. P.; Walsh, C. T.; Tang, Y. Nat. Chem. Biol. 2012, 8, 823 10.1038/nchembio.1047
19. Similar behavior was observed for VibH towards norspermidine: Keating, T. A.; Marshall, C. G.; Walsh, C. T. Biochemistry 2000, 39, 15513 10.1021/bi001651a
20. Bergendahl, V.; Linne, U.; Marahiel, M. A. Eur. J. Biochem. 2002, 269, 620 10.1046/j.0014-2956.2001.02691.x
21. Samel, S. A.; Schoenafinger, G.; Knappe, T. A.; Marahiel, M. A.; Essen, L.-O. Structure 2007, 15, 781 10.1016/j.str.2007.05.008
22. Farrell, E. K.; Merkler, D. J. Drug Discovery Today 2008, 13, 558 10.1016/j.drudis.2008.02.006
23. Cohen, L. J.; Esterhazy, D.; Kim, S. H.; Lemetre, C.; Aguilar, R. R.; Gordon, E. A.; Pickard, A. J.; Cross, J. R.; Emiliano, A. B.; Han, S. M.; Chu, J.; Vila-Farres, X.; Kaplitt, J.; Rogoz, A.; Calle, P. Y.; Hunter, C.; Bitok, J. K.; Brady, S. F. Nature 2017, 549, 48 10.1038/nature23874
24. Vizcaino, M. I.; Engel, P.; Trautman, E.; Crawford, J. M. J. Am. Chem. Soc. 2014, 136, 9244 10.1021/ja503450q
25. Torring, T.; Shames, S. R.; Cho, W.; Roy, C. R.; Crawford, J. M. ChemBioChem 2017, 18, 638 10.1002/cbic.201600618
26. Van Wagoner, R. M.; Clardy, J. Structure 2006, 14, 1425 10.1016/j.str.2006.07.005