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Ageliferin

Topic: Chemistry

 From HandWiki - Reading time: 2 min

Ageliferin is a chemical compound produced by some sponges. It was first isolated from Caribbean and then Okinawan marine sponges in the genus Agelas.[1][2][3] It often co-exists with the related compound sceptrin and other similar compounds. It has antibacterial properties and can cause biofilms to dissolve.[4] Total syntheses have been independently accomplished by the research groups of Phil S. Baran at the Scripps Research Institute,[5][6] Chuo Chen at UT Southwestern Medical Center,[7][8] Patrick Harran at UCLA,[9] and Daisuke Urabe at Toyama Prefectural University.[10]

See also

References

  1. ↑ Rinehart, Kenneth L (1990). "Bioactive Compounds from Aquatic and Terrestrial Sources". Journal of Natural Products 53 (4): 771–792. doi:10.1021/np50070a001. PMID 2095373. Bibcode: 1990JNAtP..53..771R. 
  2. ↑ Keifer, Paul A. (1991). "Bioactive Bromopyrrole Metabolites from the Caribbean Sponge Agelas conifera". J. Org. Chem. 56 (9): 2965–75. doi:10.1021/jo00009a008. 
  3. ↑ Kobayashi, Junichi (1990). "Ageliferins, potent actomyosin ATPase activators from the Okinawan marine sponge Agelas sp.". Tetrahedron 46 (16): 5579–86. doi:10.1016/S0040-4020(01)87756-5. 
  4. ↑ Laura Sanders (2009). "Sponge's secret weapon restores antibiotics' power: Bacteria treated with compound lose their resistance". Science News 175 (6): 16. doi:10.1002/scin.2009.5591750616. http://www.sciencenews.org/view/generic/id/40894/title/Sponge%27s_secret_weapon_restores_antibiotics%27_power. 
  5. ↑ Baran, Phil S.; O'Malley, Daniel P.; Zografos, Alexandros L. (2004). "Sceptrin as a Potential Biosynthetic Precursor to Complex Pyrrole–Imidazole Alkaloids: The Total Synthesis of Ageliferin". Angewandte Chemie International Edition 43 (20): 2674–2677. doi:10.1002/anie.200453937. ISSN 1521-3773. https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.200453937. 
  6. ↑ Baran, Phil S.; Li, Ke; O'Malley, Daniel P.; Mitsos, Christos (2006). "Short, Enantioselective Total Synthesis of Sceptrin and Ageliferin by Programmed Oxaquadricyclane Fragmentation". Angewandte Chemie International Edition 45 (2): 249–252. doi:10.1002/anie.200503374. ISSN 1521-3773. https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.200503374. 
  7. ↑ Wang, Xiao; Ma, Zhiqiang; Lu, Jianming; Tan, Xianghui; Chen, Chuo (2011-10-05). "Asymmetric Synthesis of Ageliferin". Journal of the American Chemical Society 133 (39): 15350–15353. doi:10.1021/ja207386q. ISSN 0002-7863. PMID 21888421. PMC 3183238. https://doi.org/10.1021/ja207386q. 
  8. ↑ Wang, Xiao; Wang, Xiaolei; Tan, Xianghui; Lu, Jianming; Cormier, Kevin W.; Ma, Zhiqiang; Chen, Chuo (2012-11-14). "A Biomimetic Route for Construction of the [4+2 and [3+2] Core Skeletons of Dimeric Pyrrole–Imidazole Alkaloids and Asymmetric Synthesis of Ageliferins"]. Journal of the American Chemical Society 134 (45): 18834–18842. doi:10.1021/ja309172t. ISSN 0002-7863. PMID 23072663. PMC 3498534. https://doi.org/10.1021/ja309172t. 
  9. ↑ Ding, Hui; Roberts, Andrew G.; Harran, Patrick G. (2012-11-29). "Total synthesis of ageliferin via acyl N-amidinyliminium ion rearrangement" (in en). Chemical Science 4 (1): 303–306. doi:10.1039/C2SC21651E. ISSN 2041-6539. PMID 23687567. PMC 3653441. https://pubs.rsc.org/en/content/articlelanding/2013/sc/c2sc21651e. 
  10. ↑ Fujino, Yudai; Fukaya, Keisuke; Urabe, Daisuke (2025-09-24). "Automated Reactivity Prediction of Complex Molecules and Its Application to Total Synthesis of Ageliferin". Journal of the American Chemical Society 147 (38): 34556–34563. doi:10.1021/jacs.5c09045. ISSN 0002-7863. https://doi.org/10.1021/jacs.5c09045. 



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