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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Chemical Compound Review: 

germacrene a     (1Z,5E)-1,5-dimethyl-8-prop- 1-en-2-yl...

Synonyms: AC1NUXAH
 
 
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High impact information on germacrene a

  • The finding that Y92F produced (+)-aristolochene (4) as 81% of the product, accompanied by 7% 5 and 12% 2, rules out Tyr-92 as the active site Lewis acid that is responsible for protonation of the germacrene A intermediate in the formation of aristolochene (4) [1].
  • Isoprenoid biosynthesis in Artemisia annua: Cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library [2].
 

Biological context of germacrene a

  • On the basis of the X-ray structure of AS, Tyr 92 was postulated to be the active-site acid responsible for protonation of germacrene A (Caruthers, J. M.; Kang, I.; Rynkiewicz, M. J.; Cane, D. E.; Christianson, D. W. J. Biol. Chem. 2000, 275, 25533-25539) [3].

References

  1. Aristolochene synthase: mechanistic analysis of active site residues by site-directed mutagenesis. Felicetti, B., Cane, D.E. J. Am. Chem. Soc. (2004) [Pubmed]
  2. Isoprenoid biosynthesis in Artemisia annua: Cloning and heterologous expression of a germacrene A synthase from a glandular trichome cDNA library. Bertea, C.M., Voster, A., Verstappen, F.W., Maffei, M., Beekwilder, J., Bouwmeester, H.J. Arch. Biochem. Biophys. (2006) [Pubmed]
  3. Germacrene A is a product of the aristolochene synthase-mediated conversion of farnesylpyrophosphate to aristolochene. Calvert, M.J., Ashton, P.R., Allemann, R.K. J. Am. Chem. Soc. (2002) [Pubmed]
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