(-)-alpha-pinene synthase

(-)-alpha-pinene synthase
Identifiers
EC number 4.2.3.119
Databases
IntEnz IntEnz view
BRENDA BRENDA entry
ExPASy NiceZyme view
KEGG KEGG entry
MetaCyc metabolic pathway
PRIAM profile
PDB structures RCSB PDB PDBe PDBsum

(-)-alpha-pinene synthase (EC 4.2.3.119, (-)-alpha-pinene/(-)-camphene synthase, (-)-alpha-pinene cyclase) is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase (cyclizing, (-)-alpha-pinene-forming).[1][2][3][4][5][6][7][8][9][10][11][12][13][14] This enzyme catalyses the following chemical reaction

geranyl diphosphate \rightleftharpoons (-)-alpha-pinene + diphosphate

Cyclase II of Salvia officinalis (sage) gives about equal parts (-)-alpha-pinene, (-)-beta-pinene and (-)-camphene.

References

  1. ↑ Gambliel, H. and Croteau, R. (1984). "Pinene cyclases I and II. Two enzymes from sage (Salvia officinalis) which catalyze stereospecific cyclizations of geranyl pyrophosphate to monoterpene olefins of opposite configuration". J. Biol. Chem. 259 (2): 740–748. PMID 6693393.
  2. ↑ Croteau, R.B., Wheeler, C.J., Cane, D.E., Ebert, R. and Ha, H.J. (1987). "Isotopically sensitive branching in the formation of cyclic monoterpenes: proof that (-)-α-pinene and (-)-β-pinene are synthesized by the same monoterpene cyclase via deprotonation of a common intermediate". Biochemistry 26 (17): 5383–5389. doi:10.1021/bi00391a025. PMID 3314988.
  3. ↑ Croteau, R., Satterwhite, D.M., Cane, D.E. and Chang, C.C. (1988). "Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of (+)- and (-)-linalyl pyrophosphate to (+)- and (-)-pinene and (+)- and (-)-camphene". J. Biol. Chem. 263 (21): 10063–10071. PMID 3392006.
  4. ↑ Croteau, R. and Satterwhite, D.M. (1989). "Biosynthesis of monoterpenes. Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (-)-pinene cyclases from sage". J. Biol. Chem. 264 (26): 15309–15315. PMID 2768265.
  5. ↑ Pyun, H.J., Wagschal, K.C., Jung, D.I., Coates, R.M. and Croteau, R. (1994). "Stereochemistry of the proton elimination in the formation of (+)- and (-)-α-pinene by monoterpene cyclases from sage (Salvia officinalis)". Arch. Biochem. Biophys. 308: 488–496. doi:10.1006/abbi.1994.1069. PMID 8109979.
  6. ↑ Lu, S., Xu, R., Jia, J.W., Pang, J., Matsuda, S.P. and Chen, X.Y. (2002). "Cloning and functional characterization of a β-pinene synthase from Artemisia annua that shows a circadian pattern of expression". Plant Physiol. 130: 477–486. doi:10.1104/pp.006544. PMID 12226526.
  7. ↑ Lewinsohn, E., Gijzen, M. and Croteau, R. (1992). "Wound-inducible pinene cyclase from grand fir: purification, characterization, and renaturation after SDS-PAGE". Arch. Biochem. Biophys. 293 (1): 167–173. doi:10.1016/0003-9861(92)90380-f. PMID 1731633.
  8. ↑ Bohlmann, J., Steele, C.L. and Croteau, R. (1997). "Monoterpene synthases from grand fir (Abies grandis). cDNA isolation, characterization, and functional expression of myrcene synthase, (-)-(4S)-limonene synthase, and (-)-(1S,5S)-pinene synthase". J. Biol. Chem. 272: 21784–21792. doi:10.1074/jbc.272.35.21784. PMID 9268308.
  9. ↑ Bohlmann, J., Phillips, M., Ramachandiran, V., Katoh, S. and Croteau, R. (1999). "cDNA cloning, characterization, and functional expression of four new monoterpene synthase members of the Tpsd gene family from grand fir (Abies grandis)". Arch. Biochem. Biophys. 368 (2): 232–243. doi:10.1006/abbi.1999.1332. PMID 10441373.
  10. ↑ Hyatt, D.C. and Croteau, R. (2005). "Mutational analysis of a monoterpene synthase reaction: altered catalysis through directed mutagenesis of (-)-pinene synthase from Abies grandis". Arch. Biochem. Biophys. 439: 222–233. doi:10.1016/j.abb.2005.05.017. PMID 15978541.
  11. ↑ Phillips, M.A., Savage, T.J. and Croteau, R. (1999). "Monoterpene synthases of loblolly pine (Pinus taeda) produce pinene isomers and enantiomers". Arch. Biochem. Biophys. 372: 197–204. doi:10.1006/abbi.1999.1467. PMID 10562434.
  12. ↑ Phillips, M.A., Wildung, M.R., Williams, D.C., Hyatt, D.C. and Croteau, R. (2003). "cDNA isolation, functional expression, and characterization of (+)-α-pinene synthase and (-)-α-pinene synthase from loblolly pine (Pinus taeda): stereocontrol in pinene biosynthesis". Arch. Biochem. Biophys. 411 (2): 267–276. doi:10.1016/s0003-9861(02)00746-4. PMID 12623076.
  13. ↑ McKay, S.A., Hunter, W.L., Godard, K.A., Wang, S.X., Martin, D.M., Bohlmann, J. and Plant, A.L. (2003). "Insect attack and wounding induce traumatic resin duct development and gene expression of (-)-pinene synthase in Sitka spruce". Plant Physiol. 133 (1): 368–378. doi:10.1104/pp.103.022723. PMID 12970502.
  14. ↑ Huber, D.P.W., Philippe, R.N., Godard, K.-A., Sturrock, R.N. and Bohlmann, J. (2005). "Characterization of four terpene synthase cDNAs from methyl jasmonate-induced Douglas-fir, Pseudotsuga menziesii". Phytochemistry 66: 1427–1439. doi:10.1016/j.phytochem.2005.04.030. PMID 15921711.

External links

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