KEGG   ENZYME: 4.2.3.120Help
Entry
EC 4.2.3.120                Enzyme                                 

Name
(-)-beta-pinene synthase;
beta-geraniolene synthase;
(-)-(1S,5S)-pinene synthase;
geranyldiphosphate diphosphate lyase (pinene forming)
Class
Lyases;
Carbon-oxygen lyases;
Acting on phosphates
BRITE hierarchy
Sysname
geranyl-diphosphate diphosphate-lyase [cyclizing, (-)-beta-pinene-forming]
Reaction(IUBMB)
geranyl diphosphate = (-)-beta-pinene + diphosphate [RN:R05766]
Reaction(KEGG)
Substrate
geranyl diphosphate [CPD:C00341]
Product
(-)-beta-pinene [CPD:C06307];
diphosphate [CPD:C00013]
Comment
Cyclase II of Salvia officinalis (sage) produces about equal parts (-)-alpha-pinene, (-)-beta-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 (-)-alpha-pinene and (-)-beta-pinene [6-9]. Cyclase IV from Pinus contorta (lodgepole pine) produces 63% (-)-beta-pinene, 26% 3-carene, and traces of alpha-pinene [10]. Synthase III from Pinus taeda (loblolly pine) forms (-)-beta-pinene with traces of alpha-pinene and requires Mn2+ and K+ (Mg2+ is ineffective) [11]. A cloned enzyme from Artemisia annua (sweet wormwood) gave (-)-beta-pinene with traces of (-)-alpha-pinene [5]. The enzyme from Picea sitchensis (Sika spruce) forms 30% (-)-beta-pinene and 70% (-)-alpha-pinene [12]. See also EC 4.2.3.119, (-)-alpha-pinene synthase, EC 4.2.3.117, (-)-camphene synthase, and EC 4.2.3.107 (+)-3-carene synthase.
History
EC 4.2.3.120 created 2012
Pathway
Monoterpenoid biosynthesis
Biosynthesis of secondary metabolites
Orthology
K07384  
pinene synthase
Reference
1  [PMID:3314988]
  Authors
Croteau RB, Wheeler CJ, Cane DE, Ebert R, Ha HJ
  Title
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.
  Journal
Biochemistry. 26 (1987) 5383-9.
Reference
2  [PMID:2768265]
  Authors
Croteau R, Satterwhite DM
  Title
Biosynthesis of monoterpenes. Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (-)-pinene cyclases from sage.
  Journal
J. Biol. Chem. 264 (1989) 15309-15.
Reference
3  [PMID:3392006]
  Authors
Croteau R, Satterwhite DM, Cane DE, Chang CC
  Title
Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of  (+)- and (-)-linalyl pyrophosphate to (+)- and (-)-pinene and (+)- and (-)-camphene.
  Journal
J. Biol. Chem. 263 (1988) 10063-71.
Reference
4  [PMID:8109979]
  Authors
Pyun HJ, Wagschal KC, Jung DI, Coates RM, Croteau R
  Title
Stereochemistry of the proton elimination in the formation of (+)- and (-)-alpha-pinene by monoterpene cyclases from sage (Salvia officinalis).
  Journal
Arch. Biochem. Biophys. 308 (1994) 488-96.
Reference
5  [PMID:12226526]
  Authors
Lu S, Xu R, Jia JW, Pang J, Matsuda SP, Chen XY
  Title
Cloning and functional characterization of a beta-pinene synthase from Artemisia  annua that shows a circadian pattern of expression.
  Journal
Plant. Physiol. 130 (2002) 477-86.
  Organism
Artemisia annua
  Sequence
[up:Q94G53]
Reference
6  [PMID:1898071]
  Authors
Gijzen M, Lewinsohn E, Croteau R.
  Title
Characterization of the constitutive and wound-inducible monoterpene cyclases of grand fir (Abies grandis).
  Journal
Arch. Biochem. Biophys. 289 (1991) 267-73.
Reference
7  [PMID:1731633]
  Authors
Lewinsohn E, Gijzen M, Croteau R
  Title
Wound-inducible pinene cyclase from grand fir: purification, characterization, and renaturation after SDS-PAGE.
  Journal
Arch. Biochem. Biophys. 293 (1992) 167-73.
Reference
8  [PMID:9268308]
  Authors
Bohlmann J, Steele CL, Croteau R.
  Title
Monoterpene synthases from grand fir (Abies grandis). cDNA isolation, characterization, and functional expression of myrcene synthase, (-)-(4S)-limonene synthase, and (-)-(1S,5S)-pinene synthase.
  Journal
J. Biol. Chem. 272 (1997) 21784-92.
  Organism
Abies grandis
  Sequence
[up:O24475]
Reference
9  [PMID:15978541]
  Authors
Hyatt DC, Croteau R
  Title
Mutational analysis of a monoterpene synthase reaction: altered catalysis through directed mutagenesis of (-)-pinene synthase from Abies grandis.
  Journal
Arch. Biochem. Biophys. 439 (2005) 222-33.
Reference
10 [PMID:7625832]
  Authors
Savage TJ, Ichii H, Hume SD, Little DB, Croteau R
  Title
Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents.
  Journal
Arch. Biochem. Biophys. 320 (1995) 257-65.
Reference
11 [PMID:10562434]
  Authors
Phillips MA, Savage TJ, Croteau R
  Title
Monoterpene synthases of loblolly pine (Pinus taeda) produce pinene isomers and enantiomers.
  Journal
Arch. Biochem. Biophys. 372 (1999) 197-204.
Reference
12 [PMID:12970502]
  Authors
McKay SA, Hunter WL, Godard KA, Wang SX, Martin DM, Bohlmann J, Plant AL
  Title
Insect attack and wounding induce traumatic resin duct development and gene expression of (-)-pinene synthase in Sitka spruce.
  Journal
Plant. Physiol. 133 (2003) 368-78.
  Organism
Picea sitchensis
  Sequence
[up:Q6XDB5]
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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