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Aszonalenin

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Aszonalenin
Names
IUPAC name (2R,10S,12R)-10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclohenicosa-4,6,8,15,17,19-hexaene-13,21-dione
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C23H23N3O2/c1-4-22(2,3)23-13-18-19(27)24-16-11-7-5-9-14(16)20(28)26(18)21(23)25-17-12-8-6-10-15(17)23/h4-12,18,21,25H,1,13H2,2-3H3,(H,24,27)/t18-,21-,23+/m1/s1Key: AVLMMDWEIUEKEK-AAIMPIBUSA-N
SMILES
  • CC(C)(C=C)12C3C(=O)NC4=CC=CC=C4C(=O)N31NC5=CC=CC=C25
Properties
Chemical formula C23H23N3O2
Molar mass 373.456 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Aszonalenin is an alkaloid which is produced by Neosartorya and Aspergillus species. Aszonalenin is a neurotoxin.

References

  1. "Aszonalenin". PubChem.
  2. Whittall, John; Sutton, Peter W. (16 April 2012). Practical Methods for Biocatalysis and Biotransformations 2. John Wiley & Sons. p. 254. ISBN 978-1-119-94341-9.
  3. Grundon, M. F. (1983). Alkaloids. Royal Society of Chemistry. p. 214. ISBN 978-0-85186-367-2.
  4. Lubertozzi, David M. (2009). "Developing Aspergillus as a Host for Heterologous Expression". Biotechnology Advances. 27 (1). University of California, Berkeley: 53–75. doi:10.1016/j.biotechadv.2008.09.001. PMID 18840517.

Further reading

  • Ruchti, Jonathan; Carreira, Erick M. (2014). "Ir-Catalyzed Reverse Prenylation of 3-Substituted Indoles: Total Synthesis of (+)-Aszonalenin and (–)-Brevicompanine B". J. Am. Chem. Soc. 136 (48): 16756–16759. doi:10.1021/ja509893s. PMID 25365411.
  • Kimura, Yasuo; Hamasaki, Takashi; Nakajima, Hiromitsu; Isogai, Akira (1982). "Structure of aszonalenin, a new metabolite of Aspergillus zonatus". Tetrahedron Letters. 23 (2): 225–228. doi:10.1016/S0040-4039(00)86791-X. ISSN 0040-4039.
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