Reconstruction of cladoniamide biosynthesis reveals nonenzymatic routes to bisindole diversity

ACS Chemical Biology

Volumn 9, Issue 12, 2014, Pages 2748-2754

  Du, Yi Ling ^a   Williams, David E ^a   Patrick, Brian O ^a   Andersen, Raymond J ^a,b   Ryan, Katherine S ^a  

^a Department of Chemistry ^*  (United States)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBAZOLE DERIVATIVE; CLADONIAMIDE; ENZYME; INDOLE DERIVATIVE; METHYL GROUP; METHYLTRANSFERASE; SUCCINIMIDE; TRYPTOLINE DERIVATIVE; UNCLASSIFIED DRUG; BIOLOGICAL PRODUCT; CLADONIAMIDE G; INDOLE ALKALOID; PIPERIDINE DERIVATIVE; SUCCINIMIDE DERIVATIVE;

ARTICLE; BIOSYNTHESIS; BIOTRANSFORMATION; CATALYSIS; CONTROLLED STUDY; ESCHERICHIA COLI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLITE; METHYLATION; BACTERIAL GENE; BACTERIAL GENOME; CHEMICAL STRUCTURE; CHEMISTRY; GENE EXPRESSION; GENETICS; METABOLISM; MULTIGENE FAMILY;

BIOLOGICAL PRODUCTS; BIOTRANSFORMATION; ESCHERICHIA COLI; GENE EXPRESSION; GENES, BACTERIAL; GENOME, BACTERIAL; INDOLE ALKALOIDS; INDOLES; MOLECULAR STRUCTURE; MULTIGENE FAMILY; PIPERIDINES; SUCCINIMIDES;

EID: 84919686301     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb500728h     Document Type: Article

References (20)

1. Ryan, K. S. and Drennan, C. L. (2009) Divergent pathways in the biosynthesis of bisindole natural products Chem. Biol. 16, 351-64
2. Sánchez, C., Méndez, C., and Salas, J. A. (2006) Indolocarbazole natural products: Occurrence, biosynthesis, and biological activity Nat. Prod. Rep. 23, 1007-45
3. Williams, D. E., Davies, J., Patrick, B. O., Bottriell, H., Tarling, T., Roberge, M., and Andersen, R. J. (2008) Cladoniamides A-G, tryptophan-derived alkaloids produced in culture by Streptomyces uncialis Org. Lett. 10, 3501-4
4. Chang, F. Y. and Brady, S. F. (2011) Cloning and characterization of an environmental DNA-derived gene cluster that encodes the biosynthesis of the antitumor substance BE-54017 J. Am. Chem. Soc. 133, 9996-9999
5. Chang, F.-Y. and Brady, S. F. (2013) Discovery of indolotryptoline antiproliferative agents by homology-guided metagenomic screening Proc. Natl. Acad. Sci. U.S.A. 110, 2478-2483
6. Du, Y.-L., Ding, T., and Ryan, K. S. (2013) Biosynthetic O -methylation protects cladoniamides from self-destruction Org. Lett. 15, 2538-2541
7. Kimura, T., Kanagaki, S., Matsui, Y., Imoto, M., Watanabe, T., and Shibasaki, M. (2012) Synthesis and assignment of the absolute configuration of indenotryptoline bisindole alkaloid BE-54017 Org. Lett. 14, 4418-21
8. Loosley, B. C., Andersen, R. J., and Dake, G. R. (2013) Total synthesis of cladoniamide G Org. Lett. 15, 1152-1154
9. Ngernmeesri, P., Soonkit, S., Konkhum, A., and Kongkathip, B. (2014) Formal synthesis of (±)-cladoniamide G Tetrahedron Lett. 55, 1621-1624
10. Schütte, J., Kilgenstein, F., Fischer, M., and Koert, U. (2014) Unsymmetrical vic -tricarbonyl compounds for the total syntheses of cladoniamide G and cladoniamide F: Unsymmetrical vic -tricarbonyl compounds Eur. J. Org. Chem. 5302-5311
11. Ryan, K. S. (2011) Biosynthetic gene cluster for the cladoniamides, bis-indoles with a rearranged scaffold PloS One 6, e23694
12. Du, Y.-L., Ding, T., Patrick, B. O., and Ryan, K. S. (2013) Xenocladoniamide F, minimal indolotryptoline from the cladoniamide pathway Tetrahedron Lett. 54, 5635-5638
13. Viollier, P. H., Minas, W., Dale, G. E., Folcher, M., and Thompson, C. J. (2001) Role of acid metabolism in Streptomyces coelicolor morphological differentiation and antibiotic biosynthesis J. Bacteriol. 183, 3184-3192
14. Du, Y. L., Shen, X. L., Yu, P., Bai, L. Q., and Li, Y. Q. (2011) γ-Butyrolactone regulatory system of Streptomyces chattanoogensis links nutrient utilization, metabolism, and development Appl. Environ. Microbiol. 77, 8415-26
15. Ames, B. D., Liu, X., and Walsh, C. T. (2010) Enzymatic processing of fumiquinazoline F: A tandem oxidative-acylation strategy for the generation of multicyclic scaffolds in fungal indole alkaloid biosynthesis Biochemistry 49, 8564-8576
16. Tsunematsu, Y., Ishikawa, N., Wakana, D., Goda, Y., Noguchi, H., Moriya, H., Hotta, K., and Watanabe, K. (2013) Distinct mechanisms for spiro-carbon formation reveal biosynthetic pathway crosstalk Nat. Chem. Biol. 9, 818-825
17. Li, S., Finefield, J. M., Sunderhaus, J. D., McAfoos, T. J., Williams, R. M., and Sherman, D. H. (2012) Biochemical characterization of NotB as an FAD-dependent oxidase in the biosynthesis of notoamide indole alkaloids J. Am. Chem. Soc. 134, 788-791
18. Li, H., Zhang, Q., Li, S., Zhu, Y., Zhang, G., Zhang, H., Tian, X., Zhang, S., Ju, J., and Zhang, C. (2012) Identification and characterization of xiamycin A and oxiamycin gene cluster reveals an oxidative cyclization strategy tailoring indolosesquiterpene biosynthesis J. Am. Chem. Soc. 134, 8996-9005
19. Xu, Z., Baunach, M., Ding, L., and Hertweck, C. (2012) Bacterial synthesis of diverse indole terpene alkaloids by an unparalleled cyclization sequence Angew. Chem., Int. Ed. Engl. 124, 10439-10443
20. Howard-Jones, A. R. and Walsh, C. T. (2007) Nonenzymatic oxidative steps accompanying action of the cytochrome P450 enzymes StaP and RebP in the biosynthesis of staurosporine and rebeccamycin J. Am. Chem. Soc. 129, 11016-7