EC 4.2.3.120 - (−)-β-pinene synthase

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IntEnz Enzyme Nomenclature
EC 4.2.3.120

Names

Accepted name:
(−)-β-pinene synthase
Other names:
β-geraniolene synthase
(−)-(1S,5S)-pinene synthase
geranyldiphosphate diphosphate lyase (pinene forming)
Systematic name:
geranyl-diphosphate diphosphate-lyase [cyclizing, (−)-β-pinene-forming]

Reaction

Comments:

Cyclase II of Salvia officinalis (sage) produces about equal parts (−)-α-pinene, (−)-β-pinene and (−)-camphene, plus traces of other monoterpenoids. The enzyme, which requires Mg2+ (preferred to Mn2+), can also use (3S)-Linalyl diphosphate (preferred to (3R)-linalyl diphosphate) [1-4]. The enzyme from Abies grandis (grand fir) produces roughly equal parts of (−)-α-pinene and (−)-β-pinene [6-9]. Cyclase IV from Pinus contorta (lodgepole pine) produces 63% (−)-β-pinene, 26% 3-carene, and traces of α-pinene [10]. Synthase III from Pinus taeda (loblolly pine) forms (−)-β-pinene with traces of α-pinene and requires Mn2+ and K+ (Mg2+ is ineffective) [11]. A cloned enzyme from Artemisia annua (sweet wormwood) gave (−)-β-pinene with traces of (−)-α-pinene [5]. The enzyme from Picea sitchensis (Sika spruce) forms 30% (−)-β-pinene and 70% (−)-α-pinene [12]. See also EC 4.2.3.119, (−)-α-pinene synthase, EC 4.2.3.117, (−)-camphene synthase, and EC 4.2.3.107 (+)-3-carene synthase.

Links to other databases

Enzymes and pathways: NC-IUBMB , BRENDA , ExplorEnz , ENZYME@ExPASy , KEGG , MetaCyc , UniPathway
Structural data: CSA , EC2PDB
UniProtKB/Swiss-Prot:

References

  1. Croteau, R. B., Wheeler, C. J., Cane, D. E., Ebert, R., Ha, H. J.
    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 : 5383-5389 (1987). [PMID: 3314988]
  2. Croteau, R., Satterwhite, D. M.
    Biosynthesis of monoterpenes. Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (-)-pinene cyclases from sage.
    J. Biol. Chem. 264 : 15309-15315 (1989). [PMID: 2768265]
  3. Croteau, R., Satterwhite, D. M., Cane, D. E., Chang, C. C.
    Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of (+)- and (-)-linalyl pyrophosphate to (+)- and (-)-pinene and (+)- and (-)-camphene.
    J. Biol. Chem. 263 : 10063-10071 (1988). [PMID: 3392006]
  4. Pyun, H. J., Wagschal, K. C., Jung, D. I., Coates, R. M., Croteau, R.
    Stereochemistry of the proton elimination in the formation of (+)- and (-)-alpha-pinene by monoterpene cyclases from sage (Salvia officinalis).
    Arch. Biochem. Biophys. 308 : 488-496 (1994). [PMID: 8109979]
  5. Lu, S., Xu, R., Jia, J. W., Pang, J., Matsuda, S. P., Chen, X. Y.
    Cloning and functional characterization of a beta-pinene synthase from Artemisia annua that shows a circadian pattern of expression.
    Plant Physiol. 130 : 477-486 (2002). [PMID: 12226526]
  6. Gijzen, M., Lewinsohn, E., Croteau, R.
    Characterization of the constitutive and wound-inducible monoterpene cyclases of grand fir (Abies grandis).
    Arch. Biochem. Biophys. 289 : 267-273 (1991). [PMID: 1898071]
  7. Lewinsohn, E., Gijzen, M., Croteau, R.
    Wound-inducible pinene cyclase from grand fir: purification, characterization, and renaturation after SDS-PAGE.
    Arch. Biochem. Biophys. 293 : 167-173 (1992). [PMID: 1731633]
  8. Bohlmann, J., Steele, C. L., Croteau, R.
    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 (1997). [PMID: 9268308]
  9. Hyatt, D. C., Croteau, R.
    Mutational analysis of a monoterpene synthase reaction: altered catalysis through directed mutagenesis of (-)-pinene synthase from Abies grandis.
    Arch. Biochem. Biophys. 439 : 222-233 (2005). [PMID: 15978541]
  10. Savage, T. J., Ichii, H., Hume, S. D., Little, D. B., Croteau, R.
    Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents.
    Arch. Biochem. Biophys. 320 : 257-265 (1995). [PMID: 7625832]
  11. Phillips, M. A., Savage, T. J., Croteau, R.
    Monoterpene synthases of loblolly pine (Pinus taeda) produce pinene isomers and enantiomers.
    Arch. Biochem. Biophys. 372 : 197-204 (1999). [PMID: 10562434]
  12. McKay, S. A., Hunter, W. L., Godard, K. A., Wang, S. X., Martin, D. M., Bohlmann, J., Plant, A. L.
    Insect attack and wounding induce traumatic resin duct development and gene expression of (-)-pinene synthase in Sitka spruce.
    Plant Physiol. 133 : 368-378 (2003). [PMID: 12970502]

[EC 4.2.3.120 created 2012]