Acting on phosphates
geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-alpha-pinene-forming]
geranyl diphosphate = (+)-alpha-pinene + diphosphate [RN:
geranyl diphosphate [CPD:
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
, (+)-beta-pinene synthase, and EC
, (+)-camphene synthase.
EC 188.8.131.52 created 2012
K21981 (+)-alpha-pinene synthase
Gambliel H, Croteau R
Pinene cyclases I and II. Two enzymes from sage (Salvia officinalis) which catalyze stereospecific cyclizations of geranyl pyrophosphate to monoterpene olefins of opposite configuration.
J Biol Chem 259:740-8 (1984)
Croteau R, Satterwhite DM, Cane DE, Chang CC
Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of (+)- and (-)-linalyl pyrophosphate to (+)- and (-)-pinene and (+)- and (-)-camphene.
J Biol Chem 263:10063-71 (1988)
Wagschal KC, Pyun HJ, Coates RM, Croteau R.
Monoterpene biosynthesis: isotope effects associated with bicyclic olefin formation catalyzed by pinene synthases from sage (Salvia officinalis).
Pyun HJ, Wagschal KC, Jung DI, Coates RM, Croteau R
Stereochemistry of the proton elimination in the formation of (+)- and (-)-alpha-pinene by monoterpene cyclases from sage (Salvia officinalis).
Phillips MA, Savage TJ, Croteau R
Monoterpene synthases of loblolly pine (Pinus taeda) produce pinene isomers and enantiomers.
Phillips MA, Wildung MR, Williams DC, Hyatt DC, Croteau R
cDNA isolation, functional expression, and characterization of (+)-alpha-pinene synthase and (-)-alpha-pinene synthase from loblolly pine (Pinus taeda): stereocontrol in pinene biosynthesis.
ExPASy - ENZYME nomenclature database: 184.108.40.206