Chemistry:Varacin

From HandWiki

Varacin is a bicyclic organosulfur compound originally found in marine Ascidiacea from the Polycitor genus.[1] It contains an unusual pentathiepine (RC=CRS
5) ring.

Bioactivity

The compound reacts with DNA. Synthetic analogues have been investigated for their antimicrobial and antitumour properties.[2][3] Because of its potent biological activity and unusual and challenging ring system, it has been a popular target of efforts toward its total synthesis.[4][5][6]

Varacin and a few related polysulfane natural products potentially exhibit planar chirality.[7]

References

  1. ↑ "Varacin and three new marine antimicrobial polysulfides from the far-eastern ascidian Polycitor sp". Journal of Natural Products 58 (2): 254–8. February 1995. doi:10.1021/np50116a015. PMID 7769392. 
  2. ↑ "On the origin of cytotoxicity of the natural product varacin. A novel example of a pentathiepin reaction that provides evidence for a triatomic sulfur intermediate". Journal of the American Chemical Society 123 (42): 10379–86. October 2001. doi:10.1021/ja016495p. PMID 11603989. 
  3. ↑ "The role of amine in the mechanism of pentathiepin (polysulfur) antitumor agents". Journal of the American Chemical Society 125 (2): 396–404. January 2003. doi:10.1021/ja027416s. PMID 12517151. 
  4. ↑ "Total synthesis of the novel benzopentathiepin varacinium trifluoroacetate: the viability of "varacin-free base"". Journal of the American Chemical Society 115 (15): 7017–7018. 1993-07-01. doi:10.1021/ja00068a087. ISSN 0002-7863. 
  5. ↑ "Synthesis and Structural Properties of the Benzopentathiepins Varacin and Isolissoclinotoxin A". The Journal of Organic Chemistry 59 (20): 5955–5960. 1994-10-01. doi:10.1021/jo00099a026. ISSN 0022-3263. 
  6. ↑ "A New Route to the Synthesis of the Naturally Occurring Benzopentathiepin Varacin". Journal of the American Chemical Society 117 (27): 7261–7262. 1995-07-01. doi:10.1021/ja00132a033. 
  7. ↑ Brzostowska, Edyta M.; Paulynice, Martine; Bentley, Ronald; Greer, Alexander (2007-07-01). "Planar Chirality due to a Polysulfur Ring in Natural Pentathiepin Cytotoxins. Implications of Planar Chirality for Enantiospecific Biosynthesis and Toxicity". Chemical Research in Toxicology 20 (7): 1046–1052. doi:10.1021/tx7000465. ISSN 0893-228X. https://pubs.acs.org/doi/epdf/10.1021/tx7000465?ref=article_openPDF&. 



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Varacin&oldid=4176510"