The Enzyme Database

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EC 4.2.3.61     
Accepted name: 5-epiaristolochene synthase
Reaction: (2E,6E)-farnesyl diphosphate = (+)-5-epiaristolochene + diphosphate
For diagram of eremophilane and spirovetivane sesquiterpenoid biosynthesis, click here
Other name(s): 5-epi-aristolochene synthase; tobacco epiaristolochene synthase; farnesyl pyrophosphate cyclase (ambiguous); EAS; TEAS
Systematic name: (2E,6E)-farnesyl-diphosphate diphosphate-lyase [(+)-5-epiaristolochene-forming]
Comments: Initial cyclization gives (+)-germacrene A in an enzyme bound form which is not released to the medium.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Back, K., Yin, S. and Chappell, J. Expression of a plant sesquiterpene cyclase gene in Escherichia coli. Arch. Biochem. Biophys. 315 (1994) 527–532. [PMID: 7986100]
2.  Starks, C.M., Back, K., Chappell, J. and Noel, J.P. Structural basis for cyclic terpene biosynthesis by tobacco 5-epi-aristolochene synthase. Science 277 (1997) 1815–1820. [PMID: 9295271]
3.  Back, K., He, S., Kim, K.U. and Shin, D.H. Cloning and bacterial expression of sesquiterpene cyclase, a key branch point enzyme for the synthesis of sesquiterpenoid phytoalexin capsidiol in UV-challenged leaves of Capsicum annuum. Plant Cell Physiol. 39 (1998) 899–904. [PMID: 9816674]
4.  Rising, K.A., Starks, C.M., Noel, J.P. and Chappell, J. Demonstration of germacrene A as an intermediate in 5-epi-aristolochene synthase catalysis. J. Am. Chem. Soc. 122 (2000) 1861–1866.
5.  Bohlmann, J., Stauber, E.J., Krock, B., Oldham, N.J., Gershenzon, J. and Baldwin, I.T. Gene expression of 5-epi-aristolochene synthase and formation of capsidiol in roots of Nicotiana attenuata and N. sylvestris. Phytochemistry 60 (2002) 109–116. [PMID: 12009313]
6.  O'Maille, P.E., Chappell, J. and Noel, J.P. Biosynthetic potential of sesquiterpene synthases: alternative products of tobacco 5-epi-aristolochene synthase. Arch. Biochem. Biophys. 448 (2006) 73–82. [PMID: 16375847]
[EC 4.2.3.61 created 2011]
 
 


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