(-)-beta-pinene synthase

(-)-beta-pinene synthase
Identifiers
EC number 4.2.3.120
Databases
IntEnz IntEnz view
BRENDA BRENDA entry
ExPASy NiceZyme view
KEGG KEGG entry
MetaCyc metabolic pathway
PRIAM profile
PDB structures RCSB PDB PDBe PDBsum

(-)-beta-pinene synthase (EC 4.2.3.120, beta-geraniolene synthase, (-)-(1S,5S)-pinene synthase, geranyldiphosphate diphosphate lyase (pinene forming)) is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase (cyclizing, (-)-beta-pinene-forming).[1][2][3][4][5][6][7][8][9][10][11][12] This enzyme catalyses the following chemical reaction

geranyl diphosphate (-)-beta-pinene + diphosphate

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

References

  1. ↑ 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.
  2. ↑ 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.
  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. ↑ 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 (2): 488–496. doi:10.1006/abbi.1994.1069. PMID 8109979.
  5. ↑ 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 (1): 477–486. doi:10.1104/pp.006544. PMC 166579. PMID 12226526.
  6. ↑ Gijzen, M.; Lewinsohn, E.; Croteau, R. (1991). "Characterization of the constitutive and wound-inducible monoterpene cyclases of grand fir (Abies grandis)". Arch. Biochem. Biophys. 289: 267–273. doi:10.1016/0003-9861(91)90471-T. PMID 1898071.
  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. ↑ 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 (2): 222–233. doi:10.1016/j.abb.2005.05.017. PMID 15978541.
  10. ↑ Savage, T.J.; Ichii, H.; Hume, S.D.; Little, D.B.; Croteau, R. (1995). "Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents". Arch. Biochem. Biophys. 320 (2): 257–265. doi:10.1016/0003-9861(95)90008-x. PMID 7625832.
  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 (1): 197–204. doi:10.1006/abbi.1999.1467. PMID 10562434.
  12. ↑ 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.
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