Stemodene

Last updated
Stemodene
Stemodene.svg
Names
Preferred IUPAC name
(4aS,6aS,8S,11aR,11bS)-4,4,11b-Trimethyl-9-methylidenetetradecahydro-8,11a-methanocyclohepta[a]naphthalene
Identifiers
3D model (JSmol)
10812290
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C20H32/c1-14-8-11-20-13-15(14)12-16(20)6-7-17-18(2,3)9-5-10-19(17,20)4/h15-17H,1,5-13H2,2-4H3/t15-,16-,17-,19-,20+/m0/s1
    Key: GNNRCBBKCVNPSC-VDWQKOAOSA-N
  • [H][C@@]12CC[C@@]3([H])C(C)(C)CCC[C@]3(C)[C@]1(CCC4=C)C[C@@H]4C2
Properties
C20H32
Molar mass 272.476 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Stemodene is a labdane-related diterpene whose corresponding terpene synthase has been discovered in rice and subsequently cloned and functionally characterized. The gene responsible for stemodene production has not been found in the completed rice genome, thus suggesting that perhaps other genes are as yet undiscovered in the "completed" genome. Stemarene synthase demonstrates high sequence homology with stemodene synthase, thus accounting for the latter's discovery by Dana Morrone in 2005. [1] Additionally, the corresponding olefin produced by each cyclase shows structural similarities and is derived from the common precursor of syn-copalyl diphosphate.

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Stemar-13-ene synthase is an enzyme with systematic name 9α-copalyl-diphosphate diphosphate-lyase (stemar-13-ene-forming). This enzyme catalyses the following chemical reaction

Stemod-13(17)-ene synthase is an enzyme with systematic name 9α-copalyl-diphosphate diphosphate-lyase . This enzyme catalyses the following chemical reaction

Elisabethatriene synthase is an enzyme with systematic name geranylgeranyl-diphosphate diphosphate-lyase (elisabethatriene-forming). This enzyme catalyses the following chemical reaction

Labdatriene synthase is an enzyme with systematic name 9α-copalyl-diphosphate diphosphate-lyase . This enzyme catalyses the following chemical reaction

ent-Isokaurene synthase is an enzyme with systematic name ent-copalyl-diphosphate diphosphate-lyase . This enzyme catalyses the following chemical reaction

(+)-Car-3-ene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-car-3-ene-forming]. This enzyme catalyses the following chemical reaction

(–)-α-Pinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (–)-α-pinene-forming]. This enzyme catalyses the following chemical reaction

Akhilesh Kumar Tyagi is an Indian plant biologist and the former director of National Institute of Plant Genome Research. Known for his studies on plant genomics and biotechnology, Tyagi is an elected fellow of all the three major Indian science academies namely Indian Academy of Sciences, Indian National Science Academy and National Academy of Sciences, India as well as The World Academy of Sciences and the National Academy of Agricultural Sciences. The Department of Biotechnology of the Government of India awarded him the National Bioscience Award for Career Development, one of the highest Indian science awards, for his contributions to biosciences in 1999.

References

  1. Morrone, Dana; Yinghua Jin; Meimei Xu; Suh-Yeon Choi; Robert M. Coates; Reuben J. Peters (April 15, 2006). "An unexpected diterpene cyclase from rice: functional identification of a stemodene synthase" (PDF). Archives of Biochemistry and Biophysics. 448 (1–2): 133–140. doi:10.1016/j.abb.2005.09.001. PMID   16256063. Archived from the original (PDF) on 2007-09-28. Retrieved 2006-11-07.