Adhikari, A., Teijaro, C. N., Townsend, C. A. & Shen, B. in Comprehensive Natural Products III (eds Liu H.-W. & Begley T. P.) 365–414 (Elsevier, 2020).
Konishi, M. et al. Dynemicin A, a novel antibiotic with the anthraquinone and 1,5-diyn-3-ene subunit. J. Antibiot. 42, 1449–1452 (1989).
Van Lanen, S. G. & Shen, B. Biosynthesis of enediyne antitumor antibiotics. Curr. Top. Med. Chem. 8, 448–459 (2008).
Article PubMed PubMed Central Google Scholar
Igarashi, M. et al. Sealutomicins, new enediyne antibiotics from the deep-sea actinomycete Nonomuraea sp. MM565M-173N2. J. Antibiot. 74, 291–299 (2021).
Maeda, H. SMANCS and polymer-conjugated macromolecular drugs: advantages in cancer chemotherapy. Adv. Drug Deliv. Rev. 46, 169–185 (2001).
Article CAS PubMed Google Scholar
Adhikari, A., Shen, B. & Rader, C. Challenges and opportunities to develop enediyne natural products as payloads for antibody–drug conjugates. Antib. Ther. 4, 1–15 (2021).
CAS PubMed PubMed Central Google Scholar
Nicolaou, K. C. et al. Uncialamycin-based antibody–drug conjugates: unique enediyne ADCs exhibiting bystander killing effect. Proc. Natl Acad. Sci. USA 118, e2107042118 (2021).
Article CAS PubMed PubMed Central Google Scholar
Yan, X. et al. Strain prioritization and genome mining for enediyne natural products. mBio 7, e02104–e02116 (2016).
Article CAS PubMed PubMed Central Google Scholar
Hindra et al. Submerged fermentation of Streptomyces uncialis providing a biotechnology platform for uncialamycin biosynthesis, engineering, and production. J. Ind. Microbiol. Biotechnol. 48, kuab025 (2021).
Article CAS PubMed PubMed Central Google Scholar
Lee, M. D. et al. Calichemicins, a novel family of antitumor antibiotics. 1. Chemistry and partial structure of calichemicin .gamma.1I. J. Am. Chem. Soc. 109, 3464–3466 (1987).
Davies, J. et al. Uncialamycin, a new enediyne antibiotic. Org. Lett. 7, 5233–5236 (2005).
Article CAS PubMed Google Scholar
Otani, T., Yoshida, K., Sasaki, T. & Minami, Y. C-1027 enediyne chromophore: presence of another active form and its chemical structure. J. Antibiot. 52, 415–421 (1999).
Komano, K. et al. Total synthesis and structure revision of the (−)-maduropeptin chromophore. J. Am. Chem. Soc. 131, 12072–12073 (2009).
Article CAS PubMed Google Scholar
Zhang, J. et al. A phosphopantetheinylating polyketide synthase producing a linear polyene to initiate enediyne antitumor antibiotic biosynthesis. Proc. Natl Acad. Sci. USA 105, 1460–1465 (2008).
Article CAS PubMed PubMed Central Google Scholar
Horsman, G. P., Chen, Y., Thorson, J. S. & Shen, B. Polyketide synthase chemistry does not direct biosynthetic divergence between 9- and 10-membered enediynes. Proc. Natl Acad. Sci. USA 107, 11331–11335 (2010).
Article CAS PubMed PubMed Central Google Scholar
Belecki, K., Crawford, J. M. & Townsend, C. A. Production of octaketide polyenes by the calicheamicin polyketide synthase CalE8: implications for the biosynthesis of enediyne core structures. J. Am. Chem. Soc. 131, 12564–12566 (2009).
Article CAS PubMed PubMed Central Google Scholar
Kong, R. et al. Characterization of a carbonyl-conjugated polyene precursor in 10-membered enediyne biosynthesis. J. Am. Chem. Soc. 130, 8142–8143 (2008).
Article CAS PubMed Google Scholar
Belecki, K. & Townsend, C. A. Environmental control of the calicheamicin polyketide synthase leads to detection of a programmed octaketide and a proposal for enediyne biosynthesis. Angew. Chem. Int. Ed. 51, 11316–11319 (2012).
Chen, X., Guo, Z.-F., Lai, P. M., Sze, K. H. & Guo, Z. Identification of a nonaketide product for the iterative polyketide synthase in biosynthesis of the nine-membered enediyne C-1027. Angew. Chem. Int. Ed. 49, 7926–7928 (2010).
Cohen, D. R. & Townsend, C. A. A dual role for a polyketide synthase in dynemicin enediyne and anthraquinone biosynthesis. Nat. Chem. 10, 231–236 (2018).
Article CAS PubMed Google Scholar
Pan, J. et al. Discovery of pentaene polyols by the activation of an enediyne gene cluster: biosynthetic implications for 9-membered enediyne core structures. Chem. Sci. 13, 13475–13481 (2022).
Article CAS PubMed PubMed Central Google Scholar
Bhardwaj, M. et al. A discrete intermediate for the biosynthesis of both the enediyne core and the anthraquinone moiety of enediyne natural products. Proc. Natl Acad. Sci. USA 120, e2220468120 (2023).
Article CAS PubMed PubMed Central Google Scholar
Cohen, D. R. & Townsend, C. A. Characterization of an anthracene intermediate in dynemicin biosynthesis. Angew. Chem. Int. Ed. 57, 5650–5654 (2018).
Liu, W. et al. Rapid PCR amplification of minimal enediyne polyketide synthase cassettes leads to a predictive familial classification model. Proc. Natl Acad. Sci. USA 100, 11959–11963 (2003).
Article CAS PubMed PubMed Central Google Scholar
Zazopoulos, E. et al. A genomics-guided approach for discovering and expressing cryptic metabolic pathways. Nat. Biotechnol. 21, 187–190 (2003).
Article CAS PubMed Google Scholar
Yan, X. et al. Comparative studies of the biosynthetic gene clusters for anthraquinone-fused enediynes shedding light into the tailoring steps of tiancimycin biosynthesis. Org. Lett. 20, 5918–5921 (2018).
Article CAS PubMed PubMed Central Google Scholar
Gui, C. et al. Intramolecular C–C bond formation links anthraquinone and enediyne scaffolds in tiancimycin biosynthesis. J. Am. Chem. Soc. 144, 20452–20462 (2022).
Article CAS PubMed PubMed Central Google Scholar
Kosgei, A. J. et al. The crystal structure of DynF from the dynemicin-biosynthesis pathway of Micromonospora chersina. Acta Crystallogr. F 78, 1–7 (2022).
Ma, G.-L. et al. Pathway retrofitting yields insights into the biosynthesis of anthraquinone-fused enediynes. J. Am. Chem. Soc. 143, 11500–11509 (2021).
Article CAS PubMed Google Scholar
Li, X., Lv, J. M., Hu, D. & Abe, I. Biosynthesis of alkyne-containing natural products. RSC Chem. Biol. 2, 166–180 (2021).
Article CAS PubMed Google Scholar
Minto, R. E. & Blacklock, B. J. Biosynthesis and function of polyacetylenes and allied natural products. Prog. Lipid Res. 47, 233–306 (2008).
Article CAS PubMed PubMed Central Google Scholar
Shi Shun, A. L. K. & Tykwinski, R. R. Synthesis of naturally occurring polyynes. Angew. Chem. Int. Ed. 45, 1034–1057 (2006).
Mullins, A. J. et al. Discovery of the Pseudomonas polyyne protegencin by a phylogeny-guided study of polyyne biosynthetic gene cluster diversity. mBio 12, e0071521 (2021).
Wang, L., Zhou, X., Fredimoses, M., Liao, S. & Liu, Y. Naturally occurring organoiodines. RSC Adv. 4, 57350–57376 (2014).
Boudreau, P. D. et al. Expanding the described metabolome of the marine cyanobacterium Moorea producens JHB through orthogonal natural products workflows. PLoS ONE 10, e0133297 (2015).
Article PubMed PubMed Central Google Scholar
Gribble, G. W.A survey of recently discovered naturally occurring organohalogen compounds. J. Nat. Prod. 87, 1285–1305 (2024).
Article CAS PubMed Google Scholar
Maiese, W. M. et al. Calicheamicins, a novel family of antitumor antibiotics: taxonomy, fermentation and biological properties. J. Antibiot. 42, 558–563 (1989).
Hensens, O. D., Giner, J. L. & Goldberg, I. H. Biosynthesis of NCS Chrom A, the chromophore of the antitumor antibiotic neocarzinostatin. J. Am. Chem. Soc. 111, 3295–3299 (1989).
Rudolf, J. D., Yan, X. & Shen, B. Genome neighborhood network reveals insights into enediyne biosynthesis and facilitates prediction and prioritization for discovery. J. Ind. Microbiol. Biotechnol. 43, 261–276 (2016).
留言 (0)