EC 4.2.3.121 - (+)-α-pinene synthase

  IntEnz view ENZYME view

IntEnz Enzyme Nomenclature
EC 4.2.3.121

Names

Accepted name:
(+)-α-pinene synthase
Other names:
(+)-α-pinene cyclase
cyclase I
Systematic name:
geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-α-pinene-forming]

Reaction

Comments:

Cyclase I of Salvia officinalis (sage) gives about equal parts (+)-α-pinene and (+)-camphene, whereas cyclase III gives about equal parts of (+)-α-pinene and (+)-β-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) (+)-β-pinene was the only product [5,6]. Requires Mn2+ (preferred to Mg2+). See also EC 4.2.3.122, (+)-β-pinene synthase, and EC 4.2.3.116, (+)-camphene 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. 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 : 740-748 (1984). [PMID: 6693393]
  2. 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]
  3. Wagschal, K. C., Pyun, H. J., Coates, R. M., Croteau, R.
    Monoterpene biosynthesis: isotope effects associated with bicyclic olefin formation catalyzed by pinene synthases from sage (Salvia officinalis).
    Arch. Biochem. Biophys. 308 : 477-487 (1994). [PMID: 8109978]
  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. 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]
  6. Phillips, M. A., Wildung, M. R., Williams, D. C., Hyatt, D. C., 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.
    Arch. Biochem. Biophys. 411 : 267-276 (2003). [PMID: 12623076]

[EC 4.2.3.121 created 2012]