KEGG   ENZYME: 4.2.3.121Help
Entry
EC 4.2.3.121                Enzyme                                 

Name
(+)-alpha-pinene synthase;
(+)-alpha-pinene cyclase;
cyclase I
Class
Lyases;
Carbon-oxygen lyases;
Acting on phosphates
BRITE hierarchy
Sysname
geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-alpha-pinene-forming]
Reaction(IUBMB)
geranyl diphosphate = (+)-alpha-pinene + diphosphate [RN:R09974]
Reaction(KEGG)
Substrate
geranyl diphosphate [CPD:C00341]
Product
(+)-alpha-pinene [CPD:C06306];
diphosphate [CPD:C00013]
Comment
Cyclase I of Salvia officinalis (sage) gives about equal parts (+)-alpha-pinene and (+)-camphene, whereas cyclase III gives about equal parts of (+)-alpha-pinene and (+)-beta-pinene. (3R)-Linalyl diphosphate can also be used by the enzyme in preference to (3S)-linalyl diphosphate. The 4-pro-R-hydrogen of geranyl diphosphate is lost. Requires Mg2+ (preferred to Mn2+) [1-4]. With synthase II of Pinus taeda (loblolly pine) (+)-alpha-pinene was the only product [5,6]. Requires Mn2+ (preferred to Mg2+). See also EC 4.2.3.122, (+)-beta-pinene synthase, and EC 4.2.3.116, (+)-camphene synthase.
History
EC 4.2.3.121 created 2012
Orthology
K21981  
(+)-alpha-pinene synthase
Reference
1  [PMID:6693393]
  Authors
Gambliel H, Croteau R
  Title
Pinene cyclases I and II. Two enzymes from sage (Salvia officinalis) which catalyze stereospecific cyclizations of geranyl pyrophosphate to monoterpene olefins of opposite configuration.
  Journal
J. Biol. Chem. 259 (1984) 740-8.
Reference
2  [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
3  [PMID:8109978]
  Authors
Wagschal KC, Pyun HJ, Coates RM, Croteau R.
  Title
Monoterpene biosynthesis: isotope effects associated with bicyclic olefin formation catalyzed by pinene synthases from sage (Salvia officinalis).
  Journal
Arch. Biochem. Biophys. 308 (1994) 477-87.
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: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
6  [PMID:12623076]
  Authors
Phillips MA, Wildung MR, Williams DC, Hyatt DC, Croteau R
  Title
cDNA isolation, functional expression, and characterization of (+)-alpha-pinene synthase and (-)-alpha-pinene synthase from loblolly pine (Pinus taeda): stereocontrol in pinene biosynthesis.
  Journal
Arch. Biochem. Biophys. 411 (2003) 267-76.
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
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BRENDA, the Enzyme Database: 

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