(-)-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 (-)-alpha-pinene + diphosphate

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

References

  1. ↑ Gambliel, H.; 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.; 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.; 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.; 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.; 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.; 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. PMC 166579. PMID 12226526.
  7. ↑ Lewinsohn, E.; Gijzen, M.; 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.; 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.; 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.; 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.; 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.; 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.; 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. PMC 196613. PMID 12970502.
  14. ↑ Huber, D.P.W.; Philippe, R.N.; Godard, K.-A.; Sturrock, R.N.; 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.
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