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(−)-alpha-pinene synthase

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(-)-alpha-pinene synthase
Identifiers
EC no.4.2.3.119
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(-)-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 (January 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". The Journal of Biological Chemistry. 259 (2): 740–8. PMID 6693393.
  2. ^ 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.
  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. ^ 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.
  5. ^ 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.
  6. ^ 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.
  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. ^ Bohlmann J, Phillips M, Ramachandiran V, Katoh S, Croteau R (August 1999). "cDNA cloning, characterization, and functional expression of four new monoterpene synthase members of the Tpsd gene family from grand fir (Abies grandis)". Archives of Biochemistry and Biophysics. 368 (2): 232–43. doi:10.1006/abbi.1999.1332. PMID 10441373.
  10. ^ 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.
  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. ^ Phillips MA, Wildung MR, Williams DC, Hyatt DC, Croteau R (March 2003). "cDNA isolation, functional expression, and characterization of (+)-alpha-pinene synthase and (-)-alpha-pinene synthase from loblolly pine (Pinus taeda): stereocontrol in pinene biosynthesis". Archives of Biochemistry and Biophysics. 411 (2): 267–76. doi:10.1016/s0003-9861(02)00746-4. PMID 12623076.
  13. ^ 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.
  14. ^ Huber DP, Philippe RN, Godard KA, Sturrock RN, Bohlmann J (June 2005). "Characterization of four terpene synthase cDNAs from methyl jasmonate-induced Douglas-fir, Pseudotsuga menziesii". Phytochemistry. 66 (12): 1427–39. doi:10.1016/j.phytochem.2005.04.030. PMID 15921711.
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