EC 4.2.3.107 - (+)-car-3-ene synthase

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IntEnz Enzyme Nomenclature
EC 4.2.3.107

Names

Accepted name:
(+)-car-3-ene synthase
Other names:
3-carene cyclase
3-carene synthase
3CAR
(+)-3-carene synthase
Systematic name:
geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-car-3-ene-forming]

Reaction

Comments:

The enzyme reacts with (3S)-linalyl diphosphate twice as rapidly as geranyl diphosphate, but 25 times as rapidly as (3R)-linalyl diphosphate. It is assumed that (3S)-linalyl diphosphate is normally formed as an enzyme bound intermediate in the reaction. In the reaction the 5-pro-R hydrogen of geranyl diphosphate is eliminated during cyclopropane ring formation [1,2]. In Picea abies (Norway spruce) and Picea sitchensis (Sitka spruce) terpinolene is also formed [4,6]. See EC 4.2.3.113 terpinolene synthase. (+)-Car-3-ene is associated with resistance of Picea sitchensis (Sitka spruce) to white pine weevil [6].

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. Savage, T. J., Croteau, R.
    Biosynthesis of monoterpenes: regio- and stereochemistry of (+)-3-carene biosynthesis.
    Arch. Biochem. Biophys. 305 : 581-587 (1993). [PMID: 8373196]
  2. Savage, T. J., Ichii, H., Hume, S. D., Little, D. B., Croteau, R.
    Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents.
    Arch. Biochem. Biophys. 320 : 257-265 (1995). [PMID: 7625832]
  3. Savage, T. J., Hatch, M. W., Croteau, R.
    Monoterpene synthases of Pinus contorta and related conifers. A new class of terpenoid cyclase.
    J. Biol. Chem. 269 : 4012-4020 (1994). [PMID: 8307957]
  4. Faldt, J., Martin, D., Miller, B., Rawat, S., Bohlmann, J.
    Traumatic resin defense in Norway spruce (Picea abies): methyl jasmonate-induced terpene synthase gene expression, and cDNA cloning and functional characterization of (+)-3-carene synthase.
    Plant Mol. Biol. 51 : 119-133 (2003). [PMID: 12602896]
  5. Hamberger, B., Hall, D., Yuen, M., Oddy, C., Hamberger, B., Keeling, C. I., Ritland, C., Ritland, K., Bohlmann, J.
    Targeted isolation, sequence assembly and characterization of two white spruce (Picea glauca) BAC clones for terpenoid synthase and cytochrome P450 genes involved in conifer defence reveal insights into a conifer genome.
    BMC Plant Biol. 9 : 106 (2009). [PMID: 19656416]
  6. Hall, D. E., Robert, J. A., Keeling, C. I., Domanski, D., Quesada, A. L., Jancsik, S., Kuzyk, M. A., Hamberger, B., Borchers, C. H., Bohlmann, J.
    An integrated genomic, proteomic and biochemical analysis of (+)-3-carene biosynthesis in Sitka spruce (Picea sitchensis) genotypes that are resistant or susceptible to white pine weevil.
    Plant J. 65 : 936-948 (2011). [PMID: 21323772]

[EC 4.2.3.107 created 2012]