ExplorEnz: EC 4.2.3.120

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4.2.3.120

Accepted name:

(-)-β-pinene synthase

Reaction:

geranyl diphosphate = (-)-β-pinene + diphosphate

For diagram of pinene and related monoterpenoids, click here

Glossary:

(-)-β-pinene = (1S,5S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]hept-2-ene

Other name(s):

β-geraniolene synthase; (-)-(1S,5S)-pinene synthase; geranyldiphosphate diphosphate lyase (pinene forming)

Systematic name:

geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-β-pinene-forming]

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:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Croteau, R.B., Wheeler, C.J., Cane, D.E., Ebert, R. and Ha, H.J. 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 (1987) 5383–5389. [PMID: 3314988]
2.	Croteau, R. and Satterwhite, D.M. Biosynthesis of monoterpenes. Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (-)-pinene cyclases from sage. J. Biol. Chem. 264 (1989) 15309–15315. [PMID: 2768265]
3.	Croteau, R., Satterwhite, D.M., Cane, D.E. and 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 (1988) 10063–10071. [PMID: 3392006]
4.	Pyun, H.J., Wagschal, K.C., Jung, D.I., Coates, R.M. and Croteau, R. Stereochemistry of the proton elimination in the formation of (+)- and (-)-α-pinene by monoterpene cyclases from sage (Salvia officinalis). Arch. Biochem. Biophys. 308 (1994) 488–496. [DOI] [PMID: 8109979]
5.	Lu, S., Xu, R., Jia, J.W., Pang, J., Matsuda, S.P. and Chen, X.Y. Cloning and functional characterization of a β-pinene synthase from Artemisia annua that shows a circadian pattern of expression. Plant Physiol. 130 (2002) 477–486. [DOI] [PMID: 12226526]
6.	Gijzen, M., Lewinsohn, E. and Croteau, R. Characterization of the constitutive and wound-inducible monoterpene cyclases of grand fir (Abies grandis). Arch. Biochem. Biophys. 289 (1991) 267–273. [DOI] [PMID: 1898071]
7.	Lewinsohn, E., Gijzen, M. and Croteau, R. Wound-inducible pinene cyclase from grand fir: purification, characterization, and renaturation after SDS-PAGE. Arch. Biochem. Biophys. 293 (1992) 167–173. [DOI] [PMID: 1731633]
8.	Bohlmann, J., Steele, C.L. and 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 (1997) 21784–21792. [DOI] [PMID: 9268308]
9.	Hyatt, D.C. and Croteau, R. Mutational analysis of a monoterpene synthase reaction: altered catalysis through directed mutagenesis of (-)-pinene synthase from Abies grandis. Arch. Biochem. Biophys. 439 (2005) 222–233. [DOI] [PMID: 15978541]
10.	Savage, T.J., Ichii, H., Hume, S.D., Little, D.B. and Croteau, R. Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents. Arch. Biochem. Biophys. 320 (1995) 257–265. [DOI] [PMID: 7625832]
11.	Phillips, M.A., Savage, T.J. and Croteau, R. Monoterpene synthases of loblolly pine (Pinus taeda) produce pinene isomers and enantiomers. Arch. Biochem. Biophys. 372 (1999) 197–204. [DOI] [PMID: 10562434]
12.	McKay, S.A., Hunter, W.L., Godard, K.A., Wang, S.X., Martin, D.M., Bohlmann, J. and Plant, A.L. Insect attack and wounding induce traumatic resin duct development and gene expression of (-)-pinene synthase in Sitka spruce. Plant Physiol. 133 (2003) 368–378. [DOI] [PMID: 12970502]

[EC 4.2.3.120 created 2012]