(-)-(1S,5S)-pinene synthase

(-)-beta-pinene synthase
EC no.
IntEnzIntEnz view
ExPASyNiceZyme view
MetaCycmetabolic pathway
PDB structuresRCSB PDB PDBe PDBsum

(-)-beta-pinene synthase (EC, 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.


  1. ^ Croteau RB, Wheeler CJ, Cane DE, Ebert R, Ha HJ (August 1987). "Isotopically sensitive branching in the formation of cyclic monoterpenes: proof that (-)-alpha-pinene and (-)-beta-pinene are synthesized by the same monoterpene cyclase via deprotonation of a common intermediate". Biochemistry. 26 (17): 5383–9. doi:10.1021/bi00391a025. PMID 3314988.
  2. ^ Croteau R, Satterwhite DM (September 1989). "Biosynthesis of monoterpenes. Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (-)-pinene cyclases from sage". The Journal of Biological Chemistry. 264 (26): 15309–15. PMID 2768265.
  3. ^ Croteau R, Satterwhite DM, Cane DE, Chang CC (July 1988). "Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of (+)- and (-)-linalyl pyrophosphate to (+)- and (-)-pinene and (+)- and (-)-camphene". The Journal of Biological Chemistry. 263 (21): 10063–71. PMID 3392006.
  4. ^ Pyun HJ, Wagschal KC, Jung DI, Coates RM, Croteau R (February 1994). "Stereochemistry of the proton elimination in the formation of (+)- and (-)-alpha-pinene by monoterpene cyclases from sage (Salvia officinalis)". Archives of Biochemistry and Biophysics. 308 (2): 488–96. doi:10.1006/abbi.1994.1069. PMID 8109979.
  5. ^ Lu S, Xu R, Jia JW, Pang J, Matsuda SP, Chen XY (September 2002). "Cloning and functional characterization of a beta-pinene synthase from Artemisia annua that shows a circadian pattern of expression". Plant Physiology. 130 (1): 477–86. doi:10.1104/pp.006544. PMC 166579. PMID 12226526.
  6. ^ Gijzen M, Lewinsohn E, Croteau R (September 1991). "Characterization of the constitutive and wound-inducible monoterpene cyclases of grand fir (Abies grandis)". Archives of Biochemistry and Biophysics. 289 (2): 267–73. doi:10.1016/0003-9861(91)90471-T. PMID 1898071.
  7. ^ Lewinsohn E, Gijzen M, Croteau R (February 1992). "Wound-inducible pinene cyclase from grand fir: purification, characterization, and renaturation after SDS-PAGE". Archives of Biochemistry and Biophysics. 293 (1): 167–73. doi:10.1016/0003-9861(92)90380-f. PMID 1731633.
  8. ^ Bohlmann J, Steele CL, Croteau R (August 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". The Journal of Biological Chemistry. 272 (35): 21784–92. doi:10.1074/jbc.272.35.21784. PMID 9268308.
  9. ^ Hyatt DC, Croteau R (July 2005). "Mutational analysis of a monoterpene synthase reaction: altered catalysis through directed mutagenesis of (-)-pinene synthase from Abies grandis". Archives of Biochemistry and Biophysics. 439 (2): 222–33. doi:10.1016/j.abb.2005.05.017. PMID 15978541.
  10. ^ Savage TJ, Ichii H, Hume SD, Little DB, Croteau R (July 1995). "Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents". Archives of Biochemistry and Biophysics. 320 (2): 257–65. doi:10.1016/0003-9861(95)90008-x. PMID 7625832.
  11. ^ Phillips MA, Savage TJ, Croteau R (December 1999). "Monoterpene synthases of loblolly pine (Pinus taeda) produce pinene isomers and enantiomers". Archives of Biochemistry and Biophysics. 372 (1): 197–204. doi:10.1006/abbi.1999.1467. PMID 10562434.
  12. ^ McKay SA, Hunter WL, Godard KA, Wang SX, Martin DM, Bohlmann J, Plant AL (September 2003). "Insect attack and wounding induce traumatic resin duct development and gene expression of (-)-pinene synthase in Sitka spruce". Plant Physiology. 133 (1): 368–78. doi:10.1104/pp.103.022723. PMC 196613. PMID 12970502.

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