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Chemical Compound Review

Abietadiene     (4aR,4bR,10aS)-1,1,4a- trimethyl-7-propan-2...

Synonyms: CHEBI:30232, LMPR0104050002, AC1L9EQ5, MLS003468551, SMR002134486, ...
 
 
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Disease relevance of C11878

  • Abietadiene synthase is translated as a preprotein bearing an N-terminal plastidial targeting sequence, and this form of the recombinant protein expressed in Escherichia coli proved to be unsuitable for detailed structure-function studies [1].
 

High impact information on C11878

  • Abietadiene synthase catalyzes the committed step in resin acid biosynthesis, forming a mixture of abietadiene double-bond isomers by two sequential, mechanistically distinct cyclizations at separate active sites [2].
  • The enzyme catalyzing the cyclization reaction, abietadiene synthase, was purified from stems of wounded grand fir saplings and was digested with trypsin [3].
  • Abietadiene synthase from grand fir catalyzes two sequential, mechanistically distinct cyclizations, of geranylgeranyl diphosphate and of copalyl diphosphate, in the formation of a mixture of abietadiene isomers as the committed step of diterpenoid resin acid biosynthesis [4].
  • The oleoresin secreted by grand fir (Abies grandis) is composed of resin acids derived largely from the abietane family of diterpene olefins as precursors which undergo subsequent oxidation of the C18-methyl group to a carboxyl function, for example, in the conversion of abieta-7,13-diene to abietic acid [1].
  • These and other results indicate that conversion of CPP (2) to abietadiene (4) occurs by anti S(N)' cyclization to a sandaracopimar-15-en-8-yl carbocation intermediate (13+, 13beta-methyl) followed by hydrogen transfer and methyl migration suprafacially on the si face of the vinyl group [5].
 

Associations of C11878 with other chemical compounds

References

  1. Abietadiene synthase from grand fir (Abies grandis): characterization and mechanism of action of the "pseudomature" recombinant enzyme. Peters, R.J., Flory, J.E., Jetter, R., Ravn, M.M., Lee, H.J., Coates, R.M., Croteau, R.B. Biochemistry (2000) [Pubmed]
  2. Abietadiene synthase catalysis: mutational analysis of a prenyl diphosphate ionization-initiated cyclization and rearrangement. Peters, R.J., Croteau, R.B. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  3. Abietadiene synthase from grand fir (Abies grandis). cDNA isolation, characterization, and bacterial expression of a bifunctional diterpene cyclase involved in resin acid biosynthesis. Vogel, B.S., Wildung, M.R., Vogel, G., Croteau, R. J. Biol. Chem. (1996) [Pubmed]
  4. Bifunctional abietadiene synthase: mutual structural dependence of the active sites for protonation-initiated and ionization-initiated cyclizations. Peters, R.J., Carter, O.A., Zhang, Y., Matthews, B.W., Croteau, R.B. Biochemistry (2003) [Pubmed]
  5. Stereochemistry of the cyclization-rearrangement of (+)-copalyl diphosphate to (-)-abietadiene catalyzed by recombinant abietadiene synthase from Abies grandis. Ravn, M.M., Coates, R.M., Flory, J.E., Peters, R.J., Croteau, R. Org. Lett. (2000) [Pubmed]
  6. Bifunctional abietadiene synthase: free diffusive transfer of the (+)-copalyl diphosphate intermediate between two distinct active sites. Peters, R.J., Ravn, M.M., Coates, R.M., Croteau, R.B. J. Am. Chem. Soc. (2001) [Pubmed]
  7. Diterpene resin acid biosynthesis in loblolly pine (Pinus taeda): Functional characterization of abietadiene/levopimaradiene synthase (PtTPS-LAS) cDNA and subcellular targeting of PtTPS-LAS and abietadienol/abietadienal oxidase (PtAO, CYP720B1). Ro, D.K., Bohlmann, J. Phytochemistry (2006) [Pubmed]
 
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