Uncovering the formation and selection of benzylmalonyl-CoA from the biosynthesis of splenocin and enterocin reveals a versatile way to introduce amino acids into polyketide carbon scaffolds

Journal of the American Chemical Society

Volumn 137, Issue 12, 2015, Pages 4183-4190

  Chang, Chenchen ^a   Huang, Rong ^a   Yan, Yan ^b   Ma, Hongmin ^a   Dai, Zheng ^a   Zhang, Benying ^a   Deng, Zixin ^a   Liu, Wen ^b   Qu, Xudong ^a  

^a WUHAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; BIOCHEMISTRY; BIOSYNTHESIS; CARBON; CARBOXYLATION; KETONES; MACHINERY; PLANTS (BOTANY); SCAFFOLDS;

ACYLTRANSFERASE; ALIPHATIC GROUPS; AROMATIC STRUCTURES; BIOSYNTHETIC ENGINEERINGS; BIOSYNTHETIC PATHWAY; POLYKETIDE SYNTHASES; SELECTIVE MODIFICATION; SYNTHETIC PATHWAYS;

AMINO ACIDS;

AMINO ACID; ASPARTIC ACID; CARBON; COENZYME A; ENTEROCIN; PHENYL GROUP; PHENYLALANINE; POLYKETIDE; POLYKETIDE SYNTHASE; SPLENOCIN; TYROSINE; UNCLASSIFIED DRUG; ACYLTRANSFERASE; ANTIMYCIN A1; BACTERIAL PROTEIN; BENZYL DERIVATIVE; BRIDGED COMPOUND; MALONYL COENZYME A;

ARTICLE; BIOSYNTHESIS; CARBOXYLATION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DEAMINATION; GENE CLUSTER; SYNTHESIS; ANALOGS AND DERIVATIVES; CHEMISTRY; ENZYME SPECIFICITY; ENZYMOLOGY; METABOLIC ENGINEERING; METABOLISM; STREPTOMYCES;

ACYLTRANSFERASES; ANTIMYCIN A; BACTERIAL PROTEINS; BENZYL COMPOUNDS; BIOSYNTHETIC PATHWAYS; BRIDGED COMPOUNDS; MALONYL COENZYME A; METABOLIC ENGINEERING; POLYKETIDE SYNTHASES; POLYKETIDES; STREPTOMYCES; SUBSTRATE SPECIFICITY;

EID: 84926366715     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b00728     Document Type: Article

References (52)

1. Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2012, 75, 311-335
2. Williams, G. J. Curr. Opin. Struct. Biol. 2013, 23, 603-612
3. Dunn, B. J.; Khosla, C. J. R. Soc., Interface 2013, 10, 20130297
4. Chan, Y. A.; Podevels, A. M.; Kevany, B. M.; Thomas, M. G. Nat. Prod. Rep. 2009, 26, 90-114
5. Wilson, M. C.; Moore, B. S. Nat. Prod. Rep. 2012, 29, 72-86
6. Chan, Y. A.; Boyne, M. T.; Podevels, A. M.; Klimowicz, A. K.; Handelsman, J.; Kelleher, N. L.; Thomas, M. G. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 14349-14354
7. Jia, X.; Tian, Z.; Shao, L.; Qu, X.; Zhao, Q.; Tang, J.; Tang, G.; Liu, W. Chem. Biol. 2006, 13, 575-585
8. Liu, Y.; Hazzard, C.; Eustáquio, A. S.; Reynolds, K. A.; Moore, B. S. J. Am. Chem. Soc. 2009, 131, 10376-10377
9. Mo, S.; Kim, D. H.; Lee, J. H.; Park, J. W.; Basnet, D. B.; Ban, Y. H.; Yoo, Y. J.; Chen, S.-w.; Park, S. R.; Choi, E. A.; Kim, E.; Jin, Y.-Y.; Lee, S.-K.; Park, J. Y.; Liu, Y.; Lee, M. O.; Lee, K. S.; Kim, S. J.; Kim, D.; Park, B. C.; Lee, S.-g.; Kwon, H. J.; Suh, J.-W.; Moore, B. S.; Lim, S.-K.; Yoon, Y. J. J. Am. Chem. Soc. 2010, 133, 976-985
10. Wilson, M. C.; Nam, S.-J.; Gulder, T. A. M.; Kauffman, C. A.; Jensen, P. R.; Fenical, W.; Moore, B. S. J. Am. Chem. Soc. 2011, 133, 1971-1977
11. Xu, Z.; Ding, L.; Hertweck, C. Angew. Chem., Int. Ed. 2011, 50, 4667-4670
12. Quade, N.; Huo, L.; Rachid, S.; Heinz, D. W.; Müller, R. Nat. Chem. Biol. 2012, 8, 117-124
13. Mantovani, S. M.; Moore, B. S. J. Am. Chem. Soc. 2013, 135, 18032-18035
14. An, J. H.; Kim, Y. S. Eur. J. Biochem. 1998, 257, 395-402
15. Pohl, N. L.; Hans, M.; Lee, H. Y.; Kim, Y. S.; Cane, D. E.; Khosla, C. J. Am. Chem. Soc. 2001, 123, 5822-5823
16. Hughes, A. J.; Keatinge-Clay, A. Chem. Biol. 2011, 18, 165-176
17. Koryakina, I.; Williams, G. J. ChemBioChem 2011, 12, 2289-2293
18. Koryakina, I.; McArthur, J.; Randall, S.; Draelos, M. M.; Musiol, E. M.; Muddiman, D. C.; Weber, T.; Williams, G. J. ACS Chem. Biol. 2012, 8, 200-208
19. Go, M. K.; Chow, J. Y.; Cheung, V. W. N.; Lim, Y. P.; Yew, W. S. Biochemistry 2012, 51, 4568-4579
20. Kennedy, J. Nat. Prod. Rep. 2008, 25, 25-34
21. Runguphan, W.; Qu, X.; O'Connor, S. E. Nature 2010, 468, 461-464
22. Qu, X.; Jiang, N.; Xu, F.; Shao, L.; Tang, G.; Wilkinson, B.; Liu, W. Mol. BioSyst. 2011, 7, 852-861
23. Ritchie, T. J.; Macdonald, S. J. Drug Discovery Today 2009, 14, 1101-1020
24. Ward, S. E.; Beswick, P. Expert Opin. Drug Discovery 2014, 9, 995-1003
25. Strangman, W. K.; Kwon, H. C.; Broide, D.; Jensen, P. R.; Fenical, W. J. Med. Chem. 2009, 52, 2317-2327
26. Yan, Y.; Zhang, L.; Ito, T.; Qu, X.; Asakawa, Y.; Awakawa, T.; Abe, I.; Liu, W. Org. Lett. 2012, 14, 4142-4145
27. Sandy, M.; Rui, Z.; Gallagher, J.; Zhang, W. ACS Chem. Biol. 2012, 7, 1956-1961
28. Sandy, M.; Zhu, X.; Rui, Z.; Zhang, W. Org. Lett. 2013, 15, 3396-3399
29. Liu, J.; Zhu, X.; Seipke, R. F.; Zhang, W. ACS Synth. Biol. 2014, 10.1021/sb5003136
30. Seipke, R. F.; Patrick, E.; Hutchings, M. I. PeerJ 2014, 2, e253
31. Yan, Y.; Chen, J.; Zhang, L.; Zheng, Q.; Han, Y.; Zhang, H.; Zhang, D.; Awakawa, T.; Abe, I.; Liu, W. Angew. Chem., Int. Ed. 2013, 52, 12308-12312
32. Quadri, L. E. N.; Weinreb, P. H.; Lei, M.; Nakano, M. M.; Zuber, P.; Walsh, C. T. Biochemistry 1998, 37, 1585-1595
33. Hahlbrock, K.; Scheel, D. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1989, 40, 347-369
34. Piel, J.; Hertweck, C.; Shipley, P. R.; Hunt, D. M.; Newman, M. S.; Moore, B. S. Chem. Biol. 2000, 7, 943-955
35. Bezanson, G. S.; Desaty, D.; Emes, A. V.; Vining, L. C. Can. J. Microbiol. 1970, 16, 147-151
36. Hill, A. M.; Thompson, B. L.; Harris, J. P.; Segret, R. Chem. Commun. 2003, 1358-1359
37. Yu, M.; Dai, Z.; Qu, X.; Gao, X. Genome Announce. 2015, 3, e01383-14
38. Xiang, L.; Moore, B. S. J. Bacteriol. 2003, 185, 399-404
39. Xiang, L.; Moore, B. S. J. Bacteriol. 2005, 187, 4286-4289
40. Kaneko, M.; Ohnishi, Y.; Horinouchi, S. J. Bacteriol. 2003, 185, 20-27
41. Bosello, M.; Robbel, L.; Linne, U.; Xie, X.; Marahiel, M. A. J. Am. Chem. Soc. 2011, 133, 4587-4595
42. Lazos, O.; Tosin, M.; Slusarczyk, A. L.; Boakes, S.; Cortés, J.; Sidebottom, P. J.; Leadlay, P. F. Chem. Biol. 2010, 17, 160-173
43. Hertweck, C. Angew. Chem., Int. Ed. 2009, 48, 4688-4716
44. Eustáquio, A. S.; O'Hagan, D.; Moore, B. S. J. Nat. Prod. 2010, 73, 378-382
45. Fibriansah, G.; Veetil, V. P.; Poelarends, G. J.; Thunnissen, A.-M. W. H. Biochemistry 2011, 50, 6053-6062
46. Kyndt, J. A.; Meyer, T. E.; Cusanovich, M. A.; Van Beeumen, J. J. FEBS Lett. 2002, 512, 240-244
47. Schwede, T. F.; Rétey, J.; Schulz, G. E. Biochemistry 1999, 38, 5355-5361
48. Turner, N. J. Curr. Opin. Chem. Biol. 2011, 15, 234-240
49. Raj, H.; Szymański, W.; de Villiers, J.; Rozeboom, H. J.; Veetil, V. P.; Reis, C. R.; de Villiers, M.; Dekker, F. J.; de Wildeman, S.; Quax, W. J.; Thunnissen, A.-M. W. H.; Feringa, B. L.; Janssen, D. B.; Poelarends, G. J. Nat. Chem. 2012, 4, 478-484
50. Zhu, X.; Liu, J.; Zhang, W. Nat. Chem. Biol. 2015, 11, 115-120
51. Zhang, L.; Chen, J.; Mori, T.; Yan, Y.; Liu, W.; Abe, I. Acta Crystallogr., Sect. F: Struct. Biol. Commun. 2014, 70, 734-737
52. Koryakina, I.; McArthur, J. B.; Draelos, M. M.; Williams, G. J. Org. Biomol. Chem. 2013, 11, 4449-4458