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'''(-)-beta-pinene synthase''' ({{EC number|4.2.3.120}}, ''beta-geraniolene synthase'', ''(-)-(1S,5S)-pinene synthase'', ''geranyldiphosphate diphosphate lyase (pinene forming)'') is an [[enzyme]] with system name ''geranyl-diphosphate diphosphate-lyase (cyclizing, (-)-beta-pinene-forming)''.<ref>{{cite journal | 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 |author = Croteau, R.B., Wheeler, C.J., Cane, D.E., Ebert, R. and Ha, H.J. |journal = Biochemistry |year = 1987 |volume = 26 |pages = 5383–5389 |pmid = 3314988 |issue=17 |doi=10.1021/bi00391a025}}</ref><ref>{{cite journal | title = Biosynthesis of monoterpenes. Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (-)-pinene cyclases from sage |author = Croteau, R. and Satterwhite, D.M. |journal = J. Biol. Chem. |year = 1989 |volume = 264 |pages = 15309–15315 |pmid = 2768265 |issue=26}}</ref><ref>{{cite journal | title = Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of (+)- and (-)-linalyl pyrophosphate to (+)- and (-)-pinene and (+)- and (-)-camphene |author = Croteau, R., Satterwhite, D.M., Cane, D.E. and Chang, C.C. |journal = J. Biol. Chem. |year = 1988 |volume = 263 |pages = 10063–10071 |pmid = 3392006 |issue=21}}</ref><ref>{{cite journal | title = Stereochemistry of the proton elimination in the formation of (+)- and (-)-&alpha;-pinene by monoterpene cyclases from sage (''Salvia officinalis'') |author = Pyun, H.J., Wagschal, K.C., Jung, D.I., Coates, R.M. and Croteau, R. |journal = Arch. Biochem. Biophys. |year = 1994 |volume = 308 |pages = 488–496 |pmid = 8109979 |doi=10.1006/abbi.1994.1069 |issue=2}}</ref><ref>{{cite journal | title = Cloning and functional characterization of a &beta;-pinene synthase from ''Artemisia annua'' that shows a circadian pattern of expression |author = Lu, S., Xu, R., Jia, J.W., Pang, J., Matsuda, S.P. and Chen, X.Y. |journal = Plant Physiol. |year = 2002 |volume = 130 |pages = 477–486 |pmid = 12226526 |doi=10.1104/pp.006544 |issue=1}}</ref><ref>{{cite journal | title = Characterization of the constitutive and wound-inducible monoterpene cyclases of grand fir (''Abies grandis'') |author = Gijzen, M., Lewinsohn, E. and Croteau, R. |journal = Arch. Biochem. Biophys. |year = 1991 |volume = 289 |pages = 267–273 |pmid = 1898071 |doi=10.1016/0003-9861(91)90471-T}}</ref><ref>{{cite journal | title = Wound-inducible pinene cyclase from grand fir: purification, characterization, and renaturation after SDS-PAGE |author = Lewinsohn, E., Gijzen, M. and Croteau, R. |journal = Arch. Biochem. Biophys. |year = 1992 |volume = 293 |pages = 167–173 |pmid = 1731633 |issue=1 |doi=10.1016/0003-9861(92)90380-f}}</ref><ref>{{cite journal | title = Monoterpene synthases from grand fir (''Abies grandis''). cDNA isolation, characterization, and functional expression of myrcene synthase, (-)-(4''S'')-limonene synthase, and (-)-(1''S'',5''S'')-pinene synthase |author = Bohlmann, J., Steele, C.L. and Croteau, R. |journal = J. Biol. Chem. |year = 1997 |volume = 272 |pages = 21784–21792 |pmid = 9268308 |doi=10.1074/jbc.272.35.21784}}</ref><ref>{{cite journal | title = Mutational analysis of a monoterpene synthase reaction: altered catalysis through directed mutagenesis of (-)-pinene synthase from ''Abies grandis'' |author = Hyatt, D.C. and Croteau, R. |journal = Arch. Biochem. Biophys. |year = 2005 |volume = 439 |pages = 222–233 |pmid = 15978541 |doi=10.1016/j.abb.2005.05.017 |issue=2}}</ref><ref>{{cite journal | title = Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents |author = Savage, T.J., Ichii, H., Hume, S.D., Little, D.B. and Croteau, R. |journal = Arch. Biochem. Biophys. |year = 1995 |volume = 320 |pages = 257–265 |pmid = 7625832 |issue=2 |doi=10.1016/0003-9861(95)90008-x}}</ref><ref>{{cite journal | title = Monoterpene synthases of loblolly pine (''Pinus taeda'') produce pinene isomers and enantiomers |author = Phillips, M.A., Savage, T.J. and Croteau, R. |journal = Arch. Biochem. Biophys. |year = 1999 |volume = 372 |pages = 197–204 |pmid = 10562434 |doi=10.1006/abbi.1999.1467 |issue=1}}</ref><ref>{{cite journal | title = Insect attack and wounding induce traumatic resin duct development and gene expression of (-)-pinene synthase in Sitka spruce |author = McKay, S.A., Hunter, W.L., Godard, K.A., Wang, S.X., Martin, D.M., Bohlmann, J. and Plant, A.L. |journal = Plant Physiol. |year = 2003 |volume = 133 |pages = 368–378 |pmid = 12970502 |issue=1 |doi=10.1104/pp.103.022723}}</ref> This enzyme [[catalysis|catalyses]] the following [[chemical reaction]]
'''(-)-beta-pinene synthase''' ({{EC number|4.2.3.120}}, ''beta-geraniolene synthase'', ''(-)-(1S,5S)-pinene synthase'', ''geranyldiphosphate diphosphate lyase (pinene forming)'') is an [[enzyme]] with systematic name ''geranyl-diphosphate diphosphate-lyase (cyclizing, (-)-beta-pinene-forming)''.<ref>{{cite journal | 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 |author = Croteau, R.B., Wheeler, C.J., Cane, D.E., Ebert, R. and Ha, H.J. |journal = Biochemistry |year = 1987 |volume = 26 |pages = 5383–5389 |pmid = 3314988 |issue=17 |doi=10.1021/bi00391a025}}</ref><ref>{{cite journal | title = Biosynthesis of monoterpenes. Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (-)-pinene cyclases from sage |author = Croteau, R. and Satterwhite, D.M. |journal = J. Biol. Chem. |year = 1989 |volume = 264 |pages = 15309–15315 |pmid = 2768265 |issue=26}}</ref><ref>{{cite journal | title = Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of (+)- and (-)-linalyl pyrophosphate to (+)- and (-)-pinene and (+)- and (-)-camphene |author = Croteau, R., Satterwhite, D.M., Cane, D.E. and Chang, C.C. |journal = J. Biol. Chem. |year = 1988 |volume = 263 |pages = 10063–10071 |pmid = 3392006 |issue=21}}</ref><ref>{{cite journal | title = Stereochemistry of the proton elimination in the formation of (+)- and (-)-&alpha;-pinene by monoterpene cyclases from sage (''Salvia officinalis'') |author = Pyun, H.J., Wagschal, K.C., Jung, D.I., Coates, R.M. and Croteau, R. |journal = Arch. Biochem. Biophys. |year = 1994 |volume = 308 |pages = 488–496 |pmid = 8109979 |doi=10.1006/abbi.1994.1069 |issue=2}}</ref><ref>{{cite journal | title = Cloning and functional characterization of a &beta;-pinene synthase from ''Artemisia annua'' that shows a circadian pattern of expression |author = Lu, S., Xu, R., Jia, J.W., Pang, J., Matsuda, S.P. and Chen, X.Y. |journal = Plant Physiol. |year = 2002 |volume = 130 |pages = 477–486 |pmid = 12226526 |doi=10.1104/pp.006544 |issue=1}}</ref><ref>{{cite journal | title = Characterization of the constitutive and wound-inducible monoterpene cyclases of grand fir (''Abies grandis'') |author = Gijzen, M., Lewinsohn, E. and Croteau, R. |journal = Arch. Biochem. Biophys. |year = 1991 |volume = 289 |pages = 267–273 |pmid = 1898071 |doi=10.1016/0003-9861(91)90471-T}}</ref><ref>{{cite journal | title = Wound-inducible pinene cyclase from grand fir: purification, characterization, and renaturation after SDS-PAGE |author = Lewinsohn, E., Gijzen, M. and Croteau, R. |journal = Arch. Biochem. Biophys. |year = 1992 |volume = 293 |pages = 167–173 |pmid = 1731633 |issue=1 |doi=10.1016/0003-9861(92)90380-f}}</ref><ref>{{cite journal | title = Monoterpene synthases from grand fir (''Abies grandis''). cDNA isolation, characterization, and functional expression of myrcene synthase, (-)-(4''S'')-limonene synthase, and (-)-(1''S'',5''S'')-pinene synthase |author = Bohlmann, J., Steele, C.L. and Croteau, R. |journal = J. Biol. Chem. |year = 1997 |volume = 272 |pages = 21784–21792 |pmid = 9268308 |doi=10.1074/jbc.272.35.21784}}</ref><ref>{{cite journal | title = Mutational analysis of a monoterpene synthase reaction: altered catalysis through directed mutagenesis of (-)-pinene synthase from ''Abies grandis'' |author = Hyatt, D.C. and Croteau, R. |journal = Arch. Biochem. Biophys. |year = 2005 |volume = 439 |pages = 222–233 |pmid = 15978541 |doi=10.1016/j.abb.2005.05.017 |issue=2}}</ref><ref>{{cite journal | title = Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents |author = Savage, T.J., Ichii, H., Hume, S.D., Little, D.B. and Croteau, R. |journal = Arch. Biochem. Biophys. |year = 1995 |volume = 320 |pages = 257–265 |pmid = 7625832 |issue=2 |doi=10.1016/0003-9861(95)90008-x}}</ref><ref>{{cite journal | title = Monoterpene synthases of loblolly pine (''Pinus taeda'') produce pinene isomers and enantiomers |author = Phillips, M.A., Savage, T.J. and Croteau, R. |journal = Arch. Biochem. Biophys. |year = 1999 |volume = 372 |pages = 197–204 |pmid = 10562434 |doi=10.1006/abbi.1999.1467 |issue=1}}</ref><ref>{{cite journal | title = Insect attack and wounding induce traumatic resin duct development and gene expression of (-)-pinene synthase in Sitka spruce |author = McKay, S.A., Hunter, W.L., Godard, K.A., Wang, S.X., Martin, D.M., Bohlmann, J. and Plant, A.L. |journal = Plant Physiol. |year = 2003 |volume = 133 |pages = 368–378 |pmid = 12970502 |issue=1 |doi=10.1104/pp.103.022723}}</ref> This enzyme [[catalysis|catalyses]] the following [[chemical reaction]]


: [[geranyl diphosphate]] <math>\rightleftharpoons</math> (-)-[[beta-pinene]] + [[diphosphate]]
: [[geranyl diphosphate]] <math>\rightleftharpoons</math> (-)-[[beta-pinene]] + [[diphosphate]]

Revision as of 18:33, 30 March 2016

(-)-beta-pinene synthase
Identifiers
EC no.4.2.3.120
Databases
IntEnzIntEnz view
BRENDABRENDA entry
ExPASyNiceZyme view
KEGGKEGG entry
MetaCycmetabolic pathway
PRIAMprofile
PDB structuresRCSB PDB PDBe PDBsum
Search
PMCarticles
PubMedarticles
NCBIproteins

(-)-beta-pinene synthase (EC 4.2.3.120, beta-geraniolene synthase, (-)-(1S,5S)-pinene synthase, geranyldiphosphate diphosphate lyase (pinene forming)) is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase (cyclizing, (-)-beta-pinene-forming).[1][2][3][4][5][6][7][8][9][10][11][12] This enzyme catalyses the following chemical reaction

geranyl diphosphate (-)-beta-pinene + diphosphate

Cyclase II of Salvia officinalis (sage) produces about equal parts (-)-alpha-pinene, (-)-beta-pinene and (-)-camphene.

References

  1. ^ Croteau, R.B., Wheeler, C.J., Cane, D.E., Ebert, R. and Ha, H.J. (1987). "Isotopically sensitive branching in the formation of cyclic monoterpenes: proof that (-)-α-pinene and (-)-β-pinene are synthesized by the same monoterpene cyclase via deprotonation of a common intermediate". Biochemistry. 26 (17): 5383–5389. doi:10.1021/bi00391a025. PMID 3314988.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ^ Croteau, R. and Satterwhite, D.M. (1989). "Biosynthesis of monoterpenes. Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (-)-pinene cyclases from sage". J. Biol. Chem. 264 (26): 15309–15315. PMID 2768265.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ Croteau, R., Satterwhite, D.M., Cane, D.E. and Chang, C.C. (1988). "Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of (+)- and (-)-linalyl pyrophosphate to (+)- and (-)-pinene and (+)- and (-)-camphene". J. Biol. Chem. 263 (21): 10063–10071. PMID 3392006.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ Pyun, H.J., Wagschal, K.C., Jung, D.I., Coates, R.M. and Croteau, R. (1994). "Stereochemistry of the proton elimination in the formation of (+)- and (-)-α-pinene by monoterpene cyclases from sage (Salvia officinalis)". Arch. Biochem. Biophys. 308 (2): 488–496. doi:10.1006/abbi.1994.1069. PMID 8109979.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ^ Lu, S., Xu, R., Jia, J.W., Pang, J., Matsuda, S.P. and Chen, X.Y. (2002). "Cloning and functional characterization of a β-pinene synthase from Artemisia annua that shows a circadian pattern of expression". Plant Physiol. 130 (1): 477–486. doi:10.1104/pp.006544. PMID 12226526.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. ^ Gijzen, M., Lewinsohn, E. and Croteau, R. (1991). "Characterization of the constitutive and wound-inducible monoterpene cyclases of grand fir (Abies grandis)". Arch. Biochem. Biophys. 289: 267–273. doi:10.1016/0003-9861(91)90471-T. PMID 1898071.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ Lewinsohn, E., Gijzen, M. and Croteau, R. (1992). "Wound-inducible pinene cyclase from grand fir: purification, characterization, and renaturation after SDS-PAGE". Arch. Biochem. Biophys. 293 (1): 167–173. doi:10.1016/0003-9861(92)90380-f. PMID 1731633.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  8. ^ Bohlmann, J., Steele, C.L. and Croteau, R. (1997). "Monoterpene synthases from grand fir (Abies grandis). cDNA isolation, characterization, and functional expression of myrcene synthase, (-)-(4S)-limonene synthase, and (-)-(1S,5S)-pinene synthase". J. Biol. Chem. 272: 21784–21792. doi:10.1074/jbc.272.35.21784. PMID 9268308.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)
  9. ^ Hyatt, D.C. and Croteau, R. (2005). "Mutational analysis of a monoterpene synthase reaction: altered catalysis through directed mutagenesis of (-)-pinene synthase from Abies grandis". Arch. Biochem. Biophys. 439 (2): 222–233. doi:10.1016/j.abb.2005.05.017. PMID 15978541.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  10. ^ Savage, T.J., Ichii, H., Hume, S.D., Little, D.B. and Croteau, R. (1995). "Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents". Arch. Biochem. Biophys. 320 (2): 257–265. doi:10.1016/0003-9861(95)90008-x. PMID 7625832.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  11. ^ Phillips, M.A., Savage, T.J. and Croteau, R. (1999). "Monoterpene synthases of loblolly pine (Pinus taeda) produce pinene isomers and enantiomers". Arch. Biochem. Biophys. 372 (1): 197–204. doi:10.1006/abbi.1999.1467. PMID 10562434.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  12. ^ McKay, S.A., Hunter, W.L., Godard, K.A., Wang, S.X., Martin, D.M., Bohlmann, J. and Plant, A.L. (2003). "Insect attack and wounding induce traumatic resin duct development and gene expression of (-)-pinene synthase in Sitka spruce". Plant Physiol. 133 (1): 368–378. doi:10.1104/pp.103.022723. PMID 12970502.{{cite journal}}: CS1 maint: multiple names: authors list (link)

External links

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