De Boer, A. H. & de Vries-van Leeuwen, I. J. Fusicoccanes: diterpenes with surprising biological functions. Trends Plant Sci. 17, 360–368 (2012).
Ohkanda, J. Fusicoccin: a chemical modulator for 14-3-3 proteins. Chem. Lett. 50, 57–67 (2021).
Sengupta, A., Liriano, J., Bienkiewicz, E. A., Miller, B. G. & Frederich, J. H. Probing the 14-3-3 isoform-specificity profile of protein-protein interactions stabilized by fusicoccin A. ACS Omega 5, 25029–25035 (2020).
Article CAS PubMed PubMed Central Google Scholar
Molzan, M. et al. Stabilization of physical RAF/14-3-3 interaction by cotylenin A as treatment strategy for RAS mutant cancers. ACS Chem. Biol. 8, 1869–1875 (2013).
Article CAS PubMed Google Scholar
Zheng, D. et al. Cytotoxic fusicoccane-type diterpenoids from Streptomyces violascens isolated from Ailuropoda melanoleuca feces. J. Nat. Prod. 80, 837–844 (2017).
Article CAS PubMed Google Scholar
Kim, S., Shin, D.-S., Lee, T. & Oh, K.-B. Periconicins, two new fusicoccane diterpenes produced by an endophytic fungus Periconia sp. with antibacterial activity. J. Nat. Prod. 67, 448–450 (2004).
Article CAS PubMed Google Scholar
Stevers, L. M. et al. Modulators of 14-3-3 protein-protein interactions. J. Med. Chem. 61, 3755–3778 (2018).
Article CAS PubMed Google Scholar
Ikejiri, F., Honma, Y., Okada, T., Urano, T. & Suzumiya, J. Cotylenin A and tyrosine kinase inhibitors synergistically inhibit the growth of chronic myeloid leukemia cells. Int. J. Oncol. 52, 2061–2068 (2018).
Kasukabe, T., Okabe-Kado, J. & Honma, Y. Cotylenin A, a new differentiation inducer, and rapamycin cooperatively inhibit growth of cancer cells through induction of cyclin G2. Cancer Sci. 99, 1693–1698 (2008).
Article CAS PubMed Google Scholar
Asahi, K. et al. Cotylenin A, a plant-growth regulator, induces the differentiation in murine and human myeloid leukemia cells. Biochem. Biophys. Res. Commun. 238, 758–763 (1997).
Article CAS PubMed Google Scholar
Anders, C. et al. A semisynthetic fusicoccane stabilizes a protein-protein interaction and enhances the expression of K+ channels at the cell surface. Chem. Biol. 20, 583–593 (2013).
Article CAS PubMed Google Scholar
Hu, Z. et al. Fusicoccane-derived diterpenoids from Alternaria brassicicola: investigation of the structure–stability relationship and discovery of an IKKβ inhibitor. Org. Lett. 20, 5198–5202 (2018).
Article CAS PubMed Google Scholar
Li, F. et al. Modified fusicoccane-type diterpenoids from Alternaria brassicicola. J. Nat. Prod. 83, 1931–1938 (2020).
Article CAS PubMed Google Scholar
Tang, Y. et al. Structural revisions of a class of natural products: scaffolds of aglycon analogues of fusicoccins and cotylenins isolated from fungi. Angew. Chem. Int. Ed. 55, 4069–4073 (2016).
Ohkanda, J. et al. Structural effect of fusicoccin upon upregulation of 14-3-3 phospholigand interaction and cytotoxic activity. Chem. Eur. J. 24, 16066–16071 (2018).
Article CAS PubMed Google Scholar
Inoue, T. et al. Semisynthesis and biological evaluation of a cotylenin A mimic derived from fusicoccin A. Bioorg. Med. Chem. Lett. 28, 646–650 (2018).
Article CAS PubMed Google Scholar
Ono, Y. et al. Dioxygenases, key enzymes to determine the aglycon structures of fusicoccin and brassicicene, diterpene compounds produced by fungi. J. Am. Chem. Soc. 133, 2548–2555 (2011).
Article CAS PubMed Google Scholar
Kato, N., Okamoto, H. & Takeshita, H. Total synthesis of optically active cotylenol, a fungal metabolite having a leaf growth activity. Intramolecular ene reaction for an eight-membered ring formation. Tetrahedron 52, 3921–3932 (1996).
Williams, D. R., Robinson, L. A., Nevill, C. R. & Reddy, J. P. Strategies for the synthesis of fusicoccanes by Nazarov reactions of dolabelladienones: total synthesis of (+)-fusicoauritone. Angew. Chem. Int. Ed. 46, 915–918 (2007).
Uwamori, M., Osada, R., Sugiyama, R., Nagatani, K. & Nakada, M. Enantioselective total synthesis of cotylenin A. J. Am. Chem. Soc. 142, 5556–5561 (2020).
Article CAS PubMed Google Scholar
Chen, B. et al. A two-phase approach to fusicoccane synthesis to uncover a compound that reduces tumourigenesis in pancreatic cancer cells. Angew. Chem. Int. Ed. 61, e202117476 (2022).
Wang, Y.-Q., Xu, K., Min, L. & Li, C.-C. Asymmetric total syntheses of hypoestin A, albolic acid, and ceroplastol II. J. Am. Chem. Soc. 144, 10162–10167 (2022).
Article CAS PubMed Google Scholar
Sims, N. J., Bonnet, W. C., Lawson, D. M. & Wood, J. L. Enantioselective total synthesis if (+)-alterbrassicicene C. J. Am. Chem. Soc. 145, 37–40 (2023).
Article CAS PubMed Google Scholar
Zhang, X. et al. Divergent synthesis of complex diterpenes via a hybrid oxidative approach. Science 369, 799–806 (2020).
Article CAS PubMed PubMed Central Google Scholar
Tazawa, A. et al. Total biosynthesis of brassicicenes: identification of a key enzyme for skeletal diversification. Org. Lett. 20, 6178–6182 (2018).
Article CAS PubMed Google Scholar
Chakrabarty, S., Wang, Y., Perkins, J. C. & Narayan, A. R. H. Scalable biocatalytic C–H oxyfunctionalization reactions. Chem. Soc. Rev. 49, 8137–8155 (2020).
Article CAS PubMed PubMed Central Google Scholar
Fasan, R. Tuning P450 enzymes as oxidation catalysts. ACS Catal. 2, 647–666 (2012).
Lange, G. L., Neider, E. E., Orrom, W. J. & Wallace, D. J. Synthesis of the spirosesquiterpene (–)-acorenone and related cyclopentanoid monoterpenes. Can. J. Chem. 56, 1628–1633 (1978).
Uroos, M., Lewis, W., Blake, A. J. & Hayes, C. J. Total synthesis of (+)-cymbodiacetal: a re-evaluation of the biomimetic route. J. Org. Chem. 75, 8465–8470 (2010).
Article CAS PubMed Google Scholar
Fürstner, A. & Shi, N. Nozaki–Hiyama–Kishi reactions catalytic in chromium. J. Am. Chem. Soc. 118, 12349–12357 (1996).
Cope, A. C., Martin, M. M. & McKervey, M. A. Transannular reactions in medium-sized rings. Q. Rev. Chem. Soc. 20, 119–152 (1966).
Kilpatrick, M. & Luborsky, F. E. The conductance and vapor pressure of boron trifluoride in anhydrous hydrofuloric acid. J. Am. Chem. Soc. 76, 5865–5868 (1954).
Vedejs, E., Engler, D. A. & Telschow, J. E. Transition-metal peroxide reactions. Synthesis of α-hydroxycarbonyl compounds from enolates. J. Org. Chem. 43, 188–196 (1978).
Baek, M. et al. Accurate prediction of protein structures and interactions using a three-track neural network. Science 373, 871–876 (2021).
Article CAS PubMed PubMed Central Google Scholar
Zallot, R., Oberg, N. & Gerlt, J. A. The EFI web resource for genomic enzymology tools: leveraging protein, genome, and metagenome databases to discover novel enzymes and metabolic pathways. Biochemistry 58, 4169–4182 (2019).
Article CAS PubMed Google Scholar
Jiang, Y. & Renata, H. Finding superior biocatalysts via homolog screening. Chem Catal. 2, 2471–2480 (2022).
Article CAS PubMed PubMed Central Google Scholar
Kille, S. et al. Reducing codon redundancy and screening effort of combinatorial protein libraries created by saturation mutagenesis. ACS Synth. Biol. 2, 83–92 (2013).
Article CAS PubMed Google Scholar
Li, F., Deng, H. & Renata, H. Remote B-ring oxidation of sclareol with an engineered P450 facilitates divergent access to complex terpenoids. J. Am. Chem. Soc. 144, 7616–7621 (2022).
Article CAS PubMed Google Scholar
Li, J., Li, F., King-Smith, E. & Renata, H. Merging chemoenzymatic and radical-based retrosynthetic logic for rapid and modular synthesis of oxidized meroterpenoids. Nat. Chem. 12, 173–179 (2020).
留言 (0)