Genome-based discovery and total synthesis of janustatins, potent cytotoxins from a plant-associated bacterium

Wilson, M. C. et al. An environmental bacterial taxon with a large and distinct metabolic repertoire. Nature 506, 58–62 (2014).

CAS  PubMed  Article  Google Scholar 

Elshahawi, S. I. et al. Boronated tartrolon antibiotic produced by symbiotic cellulose-degrading bacteria in shipworm gills. Proc. Natl Acad. Sci. USA 110, e295–e304 (2013).

CAS  PubMed  PubMed Central  Article  Google Scholar 

Sit, C. S. et al. Variable genetic architectures produce virtually identical molecules in bacterial symbionts of fungus-growing ants. Proc. Natl Acad. Sci. USA 112, 13150–13154 (2015).

CAS  PubMed  PubMed Central  Article  Google Scholar 

Ueoka, R. et al. Genome-based identification of a plant-associated marine bacterium as a rich natural product source. Angew. Chem. Int. Ed. 130, 14727–14731 (2018).

Article  Google Scholar 

Waterworth, S. C. et al. Horizontal gene transfer to a defensive symbiont with a reduced genome in a multipartite beetle microbiome. mBio 11, e02430-19 (2020).

PubMed  PubMed Central  Article  Google Scholar 

Zan, J. et al. A microbial factory for defensive kahalalides in a tripartite marine symbiosis. Science 364, eaaw6732 (2019).

CAS  PubMed  Article  Google Scholar 

Tobias, N. J. et al. Natural product diversity associated with the nematode symbionts Photorhabdus and Xenorhabdus. Nat. Microbiol. 2, 1676–1685 (2017).

CAS  PubMed  Article  Google Scholar 

Rust, M. et al. A multiproducer microbiome generates chemical diversity in the marine sponge Mycale hentscheli. Proc. Natl Acad. Sci. USA 117, 9508–9518 (2020).

CAS  PubMed  PubMed Central  Article  Google Scholar 

Storey, M. A. et al. Metagenomic exploration of the marine sponge Mycale hentscheli uncovers multiple polyketide-producing bacterial symbionts. mBio 11, e02997-19 (2020).

PubMed  PubMed Central  Article  Google Scholar 

Freeman, M. F. et al. Metagenome mining reveals polytheonamides as posttranslationally modified ribosomal peptides. Science 338, 387–390 (2012).

CAS  PubMed  Article  Google Scholar 

Helfrich, E. J. N. & Piel, J. Biosynthesis of polyketides by trans-AT polyketide synthases. Nat. Prod. Rep. 33, 231–316 (2016).

CAS  PubMed  Article  Google Scholar 

Fuller, A. T. et al. Pseudomonic acid: an antibiotic produced by Pseudomonas fluorescens. Nature 234, 416–417 (1971).

CAS  PubMed  Article  Google Scholar 

El-Sayed, A. K. et al. Characterization of the mupirocin biosynthesis gene cluster from Pseudomonas fluorescens NCIMB 10586. Chem. Biol. 10, 419–430 (2003).

CAS  PubMed  Article  Google Scholar 

Pulsawat, N., Kitani, S. & Nihira, T. Characterization of biosynthetic gene cluster for the production of virginiamycin M, a streptogramin type A antibiotic, in Streptomyces virginiae. Gene 393, 31–42 (2007).

CAS  PubMed  Article  Google Scholar 

Mast, Y. et al. Characterization of the 'pristinamycin supercluster' of Streptomyces pristinaespiralis. Microb. Biotechnol. 4, 192–206 (2011).

CAS  PubMed  PubMed Central  Article  Google Scholar 

Cocito, C. G. Antibiotics of the virginiamycin family, inhibitors which contain synergistic components. Microbiol. Rev. 43, 145–198 (1979).

CAS  PubMed  PubMed Central  Article  Google Scholar 

Pöplau, P., Frank, S., Morinaka, B. I. & Piel, J. An enzymatic domain for the formation of cyclic ethers in complex polyketides. Angew. Chem. Int. Ed. 52, 13215–13218 (2013).

Article  CAS  Google Scholar 

Ueoka, R., Bortfeld-Miller, M., Morinaka, B. I., Vorholt, J. A. & Piel, J. Toblerols: cyclopropanol-containing polyketide modulators of antibiosis in Methylobacteria. Angew. Chem. Int. Ed. 130, 989–993 (2018).

Article  Google Scholar 

Meoded, R. A. et al. A polyketide synthase component for oxygen insertion into polyketide backbones. Angew. Chem. Int. Ed. 57, 11644–11648 (2018).

CAS  Article  Google Scholar 

Ma, M., Lohman, J. R., Liu, T. & Shen, B. C-S bond cleavage by a polyketide synthase domain. Proc. Natl Acad. Sci. USA 112, 10359–11364 (2015).

CAS  PubMed  PubMed Central  Article  Google Scholar 

Chung, E. J., Park, J. A., Jeon, C. O. & Chung, Y. R. Gynuella sunshinyii gen. nov., sp. nov., an antifungal rhizobacterium isolated from a halophyte, Carex scabrifolia Steud. Int. J. Syst. Evol. Microbiol. 65, 1038–1043 (2015).

CAS  PubMed  Article  Google Scholar 

Blin, K. et al. AntiSMASH 5.0: updates to the secondary metabolite genome mining pipeline. Nucleic Acids Res. 47, W81–W87 (2019).

CAS  PubMed  PubMed Central  Article  Google Scholar 

Helfrich, E. J. N. et al. Automated structure prediction of trans-acyltransferase polyketide synthase products. Nat. Chem. Biol. 15, 813–821 (2019).

CAS  PubMed  PubMed Central  Article  Google Scholar 

Ueoka, R. et al. Genome mining of oxidation modules in trans-acyltransferase polyketide synthases reveals a culturable source for lobatamides. Angew. Chem. Int. Ed. 59, 7761–7765 (2020).

CAS  Article  Google Scholar 

Chung, Y. R. & Khan, H. Novel nitrilase and method for preparing sangivamycin by using same. Patent KR20150047041A (2014).

Helfrich, E. J. N. et al. Evolution of combinatorial diversity in trans-acyltransferase polyketide synthase assembly lines across bacteria. Nat. Commun. 12, 1422 (2021).

CAS  PubMed  PubMed Central  Article  Google Scholar 

Nguyen, T. et al. Exploiting the mosaic structure of trans-acyltransferase polyketide synthases for natural product discovery and pathway dissection. Nat. Biotechnol. 26, 225–233 (2008).

CAS  PubMed  Article  Google Scholar 

Grindberg, R. V. et al. Single cell genome amplification accelerates identification of the apratoxin biosynthetic pathway from a complex microbial assemblage. PLoS ONE 6, e18565 (2011).

CAS  PubMed  PubMed Central  Article  Google Scholar 

Luesch, H., Yoshida, W. Y., Moore, R. E., Paul, V. J. & Corbett, T. H. Total structure determination of apratoxin A, a potent novel cytotoxin from the marine cyanobacterium Lyngbya majuscula. J. Am. Chem. Soc. 123, 5418–5423 (2001).

CAS  PubMed  Article  Google Scholar 

Buchholz, T. J. et al. Polyketide β-branching in bryostatin biosynthesis: identification of surrogate acetyl-ACP donors for BryR, an HMG-ACP synthase. Chem. Biol. 17, 1092–1100 (2010).

CAS  PubMed  PubMed Central  Article  Google Scholar 

Davidson, S. K., Allen, S. W., Lim, G. E., Anderson, C. M. & Haygood, M. G. Evidence for the biosynthesis of bryostatins by the bacterial symbiont ‘Candidatus Endobugula sertula’ of the bryozoan Bugula neritina. Appl. Environ. Microbiol. 67, 4531–4537 (2001).

CAS  PubMed  PubMed Central  Article  Google Scholar 

Skiba, M. A. et al. Repurposing the GNAT fold in the initiation of polyketide biosynthesis. Structure 28, 63–74 (2020).

CAS  PubMed  Article  Google Scholar 

Skiba, M. A. et al. A mononuclear iron-dependent methyltransferase catalyzes initial steps in assembly of the apratoxin A polyketide starter unit. ACS Chem. Biol. 12, 3039–3048 (2017).

CAS  PubMed  PubMed Central  Article  Google Scholar 

Skiba, M. A. et al. Biosynthesis of t-butyl in apratoxin A: functional analysis and architecture of a PKS loading module. ACS Chem. Biol. 13, 1640–1650 (2018).

CAS  PubMed  PubMed Central  Article  Google Scholar 

Röttig, M. et al. NRPSpredictor2—a web server for predicting NRPS adenylation domain specificity. Nucleic Acids Res. 39, W362–W367 (2011).

PubMed  PubMed Central  Article  CAS  Google Scholar 

Lu, S. et al. CDD/SPARCLE: the conserved domain database in 2020. Nucleic Acids Res. 48, D265–D268 (2020).

CAS  PubMed  Article  Google Scholar 

Hehre, W. et al. Efficient protocol for accurately calculating 13C chemical shifts of conformationally flexible natural products: scope, assessment and limitations. J. Nat. Prod. 82, 2299–2306 (2019).

CAS  PubMed  Article  Google Scholar 

Hwang, T.-L. & Shaka, A. J. Cross relaxation without TOCSY: transverse rotating-frame Overhauser effect spectroscopy. J. Am. Chem. Soc. 114, 3157–3159 (1992).

CAS  Article  Google Scholar 

Nunez-Vergara, L. J. et al. Chromenopyridines: promising scaffolds for medicinal and biological chemistry. Curr. Med. Chem. 18, 4761–4785 (2011).

CAS  PubMed  Article 

留言 (0)

沒有登入
gif