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{{Short description|Enzyme}}
{{Infobox enzyme
{{Infobox enzyme
| Name = (–)-β-pinene synthase
| Name = (−)-β-pinene synthase
| EC_number = 4.2.3.120
| EC_number = 4.2.3.120
| CAS_number =
| CAS_number =
| GO_code =
| IUBMB_EC_number = 4/2/3/120
| GO_code =
| image =
| image =
| width =
| width =
| caption =
| caption =
}}
}}
'''(–)-β-Pinene synthase''' (EC 4.2.3.120, '''β-geraniolene synthase''', '''(–)-(1''S'',5''S'')-pinene synthase''', '''geranyldiphosphate diphosphate lyase (pinene forming)''') is an [[enzyme]] with [[List of enzymes|systematic name]] '''geranyl-diphosphate diphosphate-lyase [cyclizing, (–)-β-pinene-forming]'''.<ref>{{cite journal | vauthors = Croteau RB, Wheeler CJ, Cane DE, Ebert R, Ha HJ | title = 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 | journal = Biochemistry | volume = 26 | issue = 17 | pages = 5383–9 | date = August 1987 | pmid = 3314988 | doi = 10.1021/bi00391a025 }}</ref><ref>{{cite journal | vauthors = Croteau R, Satterwhite DM | title = Biosynthesis of monoterpenes. Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (–)-pinene cyclases from sage | journal = The Journal of Biological Chemistry | volume = 264 | issue = 26 | pages = 15309–15 | date = September 1989 | pmid = 2768265 }}</ref><ref>{{cite journal | vauthors = 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 = The Journal of Biological Chemistry | volume = 263 | issue = 21 | pages = 10063–71 | date = July 1988 | pmid = 3392006 }}</ref><ref>{{cite journal | vauthors = Pyun HJ, Wagschal KC, Jung DI, Coates RM, Croteau R | title = Stereochemistry of the proton elimination in the formation of (+)- and (–)-α-pinene by monoterpene cyclases from sage (''Salvia officinalis'') | journal = Archives of Biochemistry and Biophysics | volume = 308 | issue = 2 | pages = 488–96 | date = February 1994 | pmid = 8109979 | doi = 10.1006/abbi.1994.1069 }}</ref><ref>{{cite journal | vauthors = Lu S, Xu R, Jia JW, Pang J, Matsuda SP, Chen XY | title = Cloning and functional characterization of a β-pinene synthase from ''Artemisia annua'' that shows a circadian pattern of expression | journal = Plant Physiology | volume = 130 | issue = 1 | pages = 477–86 | date = September 2002 | pmid = 12226526 | pmc = 166579 | doi = 10.1104/pp.006544 }}</ref><ref>{{cite journal | vauthors = Gijzen M, Lewinsohn E, Croteau R | title = Characterization of the constitutive and wound-inducible monoterpene cyclases of grand fir (''Abies grandis'') | journal = Archives of Biochemistry and Biophysics | volume = 289 | issue = 2 | pages = 267–73 | date = September 1991 | pmid = 1898071 | doi = 10.1016/0003-9861(91)90471-T }}</ref><ref>{{cite journal | vauthors = Lewinsohn E, Gijzen M, Croteau R | title = Wound-inducible pinene cyclase from grand fir: purification, characterization, and renaturation after SDS-PAGE | journal = Archives of Biochemistry and Biophysics | volume = 293 | issue = 1 | pages = 167–73 | date = February 1992 | pmid = 1731633 | doi = 10.1016/0003-9861(92)90380-f }}</ref><ref>{{cite journal | vauthors = Bohlmann J, Steele CL, Croteau R | 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 | journal = The Journal of Biological Chemistry | volume = 272 | issue = 35 | pages = 21784–92 | date = August 1997 | pmid = 9268308 | doi = 10.1074/jbc.272.35.21784 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Hyatt DC, Croteau R | title = Mutational analysis of a monoterpene synthase reaction: altered catalysis through directed mutagenesis of (-)-pinene synthase from ''Abies grandis'' | journal = Archives of Biochemistry and Biophysics | volume = 439 | issue = 2 | pages = 222–33 | date = July 2005 | pmid = 15978541 | doi = 10.1016/j.abb.2005.05.017 }}</ref><ref>{{cite journal | vauthors = Savage TJ, Ichii H, Hume SD, Little DB, Croteau R | title = Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents | journal = Archives of Biochemistry and Biophysics | volume = 320 | issue = 2 | pages = 257–65 | date = July 1995 | pmid = 7625832 | doi = 10.1016/0003-9861(95)90008-x }}</ref><ref>{{cite journal | vauthors = Phillips MA, Savage TJ, Croteau R | title = Monoterpene synthases of loblolly pine (''Pinus taeda'') produce pinene isomers and enantiomers | journal = Archives of Biochemistry and Biophysics | volume = 372 | issue = 1 | pages = 197–204 | date = December 1999 | pmid = 10562434 | doi = 10.1006/abbi.1999.1467 }}</ref><ref>{{cite journal | vauthors = McKay SA, Hunter WL, Godard KA, Wang SX, Martin DM, Bohlmann J, Plant AL | title = Insect attack and wounding induce traumatic resin duct development and gene expression of (-)-pinene synthase in Sitka spruce | journal = Plant Physiology | volume = 133 | issue = 1 | pages = 368–78 | date = September 2003 | pmid = 12970502 | pmc = 196613 | doi = 10.1104/pp.103.022723 }}</ref> This enzyme [[catalysis|catalyses]] the following [[chemical reaction]]
'''(−)-β-Pinene synthase''' (EC 4.2.3.120, '''β-geraniolene synthase''', '''(−)-(1''S'',5''S'')-pinene synthase''', '''geranyldiphosphate diphosphate lyase (pinene forming)''') is an [[enzyme]] with [[List of enzymes|systematic name]] '''geranyl-diphosphate diphosphate-lyase [cyclizing, (−)-β-pinene-forming]'''.<ref>{{cite journal | vauthors = Croteau RB, Wheeler CJ, Cane DE, Ebert R, Ha HJ | title = 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 | journal = Biochemistry | volume = 26 | issue = 17 | pages = 5383–9 | date = August 1987 | pmid = 3314988 | doi = 10.1021/bi00391a025 }}</ref><ref>{{cite journal | vauthors = Croteau R, Satterwhite DM | title = Biosynthesis of monoterpenes. Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (–)-pinene cyclases from sage | journal = The Journal of Biological Chemistry | volume = 264 | issue = 26 | pages = 15309–15 | date = September 1989 | doi = 10.1016/S0021-9258(19)84827-5 | doi-access = free | pmid = 2768265 }}</ref><ref>{{cite journal | vauthors = 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 = The Journal of Biological Chemistry | volume = 263 | issue = 21 | pages = 10063–71 | date = July 1988 | doi = 10.1016/S0021-9258(19)81477-1 | doi-access = free | pmid = 3392006 }}</ref><ref>{{cite journal | vauthors = Pyun HJ, Wagschal KC, Jung DI, Coates RM, Croteau R | title = Stereochemistry of the proton elimination in the formation of (+)- and (–)-α-pinene by monoterpene cyclases from sage (''Salvia officinalis'') | journal = Archives of Biochemistry and Biophysics | volume = 308 | issue = 2 | pages = 488–96 | date = February 1994 | pmid = 8109979 | doi = 10.1006/abbi.1994.1069 }}</ref><ref>{{cite journal | vauthors = Lu S, Xu R, Jia JW, Pang J, Matsuda SP, Chen XY | title = Cloning and functional characterization of a β-pinene synthase from ''Artemisia annua'' that shows a circadian pattern of expression | journal = Plant Physiology | volume = 130 | issue = 1 | pages = 477–86 | date = September 2002 | pmid = 12226526 | pmc = 166579 | doi = 10.1104/pp.006544 }}</ref><ref>{{cite journal | vauthors = Gijzen M, Lewinsohn E, Croteau R | title = Characterization of the constitutive and wound-inducible monoterpene cyclases of grand fir (''Abies grandis'') | journal = Archives of Biochemistry and Biophysics | volume = 289 | issue = 2 | pages = 267–73 | date = September 1991 | pmid = 1898071 | doi = 10.1016/0003-9861(91)90471-T }}</ref><ref>{{cite journal | vauthors = Lewinsohn E, Gijzen M, Croteau R | title = Wound-inducible pinene cyclase from grand fir: purification, characterization, and renaturation after SDS-PAGE | journal = Archives of Biochemistry and Biophysics | volume = 293 | issue = 1 | pages = 167–73 | date = February 1992 | pmid = 1731633 | doi = 10.1016/0003-9861(92)90380-f }}</ref><ref>{{cite journal | vauthors = Bohlmann J, Steele CL, Croteau R | 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 | journal = The Journal of Biological Chemistry | volume = 272 | issue = 35 | pages = 21784–92 | date = August 1997 | pmid = 9268308 | doi = 10.1074/jbc.272.35.21784 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Hyatt DC, Croteau R | title = Mutational analysis of a monoterpene synthase reaction: altered catalysis through directed mutagenesis of (-)-pinene synthase from ''Abies grandis'' | journal = Archives of Biochemistry and Biophysics | volume = 439 | issue = 2 | pages = 222–33 | date = July 2005 | pmid = 15978541 | doi = 10.1016/j.abb.2005.05.017 }}</ref><ref>{{cite journal | vauthors = Savage TJ, Ichii H, Hume SD, Little DB, Croteau R | title = Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents | journal = Archives of Biochemistry and Biophysics | volume = 320 | issue = 2 | pages = 257–65 | date = July 1995 | pmid = 7625832 | doi = 10.1016/0003-9861(95)90008-x }}</ref><ref>{{cite journal | vauthors = Phillips MA, Savage TJ, Croteau R | title = Monoterpene synthases of loblolly pine (''Pinus taeda'') produce pinene isomers and enantiomers | journal = Archives of Biochemistry and Biophysics | volume = 372 | issue = 1 | pages = 197–204 | date = December 1999 | pmid = 10562434 | doi = 10.1006/abbi.1999.1467 }}</ref><ref>{{cite journal | vauthors = McKay SA, Hunter WL, Godard KA, Wang SX, Martin DM, Bohlmann J, Plant AL | title = Insect attack and wounding induce traumatic resin duct development and gene expression of (-)-pinene synthase in Sitka spruce | journal = Plant Physiology | volume = 133 | issue = 1 | pages = 368–78 | date = September 2003 | pmid = 12970502 | pmc = 196613 | doi = 10.1104/pp.103.022723 }}</ref> This enzyme [[catalysis|catalyses]] the following [[chemical reaction]]


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


Cyclase II of ''[[Salvia officinalis]]'' (sage) produces about equal parts (–)-[[α-pinene]], (–)-β-pinene and (–)-[[camphene]].
Cyclase II of ''[[Salvia officinalis]]'' (sage) produces about equal parts (−)-[[α-pinene]], (−)-β-pinene and (−)-[[camphene]].


== References ==
== References ==
Line 19: Line 19:


== External links ==
== External links ==
* {{MeshName|(-)-beta-pinene+synthase}}
* {{MeshName|(−)-beta-pinene+synthase}}


{{Carbon-oxygen lyases}}
{{Carbon-oxygen lyases}}
Line 25: Line 25:
{{Portal bar|Biology|border=no}}
{{Portal bar|Biology|border=no}}


{{DEFAULTSORT:(-)-beta-pinene synthase}}
[[Category:EC 4.2.3]]
[[Category:EC 4.2.3]]

Latest revision as of 22:01, 6 June 2024

(−)-β-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
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PMCarticles
PubMedarticles
NCBIproteins

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

geranyl diphosphate (−)-β-pinene + diphosphate

Cyclase II of Salvia officinalis (sage) produces about equal parts (−)-α-pinene, (−)-β-pinene and (−)-camphene.

References[edit]

  1. ^ Croteau RB, Wheeler CJ, Cane DE, Ebert R, Ha HJ (August 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): 5383–9. doi:10.1021/bi00391a025. PMID 3314988.
  2. ^ Croteau R, Satterwhite DM (September 1989). "Biosynthesis of monoterpenes. Stereochemical implications of acyclic and monocyclic olefin formation by (+)- and (–)-pinene cyclases from sage". The Journal of Biological Chemistry. 264 (26): 15309–15. doi:10.1016/S0021-9258(19)84827-5. PMID 2768265.
  3. ^ Croteau R, Satterwhite DM, Cane DE, Chang CC (July 1988). "Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of (+)- and (–)-linalyl pyrophosphate to (+)- and (–)-pinene and (+)- and (–)-camphene". The Journal of Biological Chemistry. 263 (21): 10063–71. doi:10.1016/S0021-9258(19)81477-1. PMID 3392006.
  4. ^ Pyun HJ, Wagschal KC, Jung DI, Coates RM, Croteau R (February 1994). "Stereochemistry of the proton elimination in the formation of (+)- and (–)-α-pinene by monoterpene cyclases from sage (Salvia officinalis)". Archives of Biochemistry and Biophysics. 308 (2): 488–96. doi:10.1006/abbi.1994.1069. PMID 8109979.
  5. ^ Lu S, Xu R, Jia JW, Pang J, Matsuda SP, Chen XY (September 2002). "Cloning and functional characterization of a β-pinene synthase from Artemisia annua that shows a circadian pattern of expression". Plant Physiology. 130 (1): 477–86. doi:10.1104/pp.006544. PMC 166579. PMID 12226526.
  6. ^ Gijzen M, Lewinsohn E, Croteau R (September 1991). "Characterization of the constitutive and wound-inducible monoterpene cyclases of grand fir (Abies grandis)". Archives of Biochemistry and Biophysics. 289 (2): 267–73. doi:10.1016/0003-9861(91)90471-T. PMID 1898071.
  7. ^ Lewinsohn E, Gijzen M, Croteau R (February 1992). "Wound-inducible pinene cyclase from grand fir: purification, characterization, and renaturation after SDS-PAGE". Archives of Biochemistry and Biophysics. 293 (1): 167–73. doi:10.1016/0003-9861(92)90380-f. PMID 1731633.
  8. ^ Bohlmann J, Steele CL, Croteau R (August 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". The Journal of Biological Chemistry. 272 (35): 21784–92. doi:10.1074/jbc.272.35.21784. PMID 9268308.
  9. ^ Hyatt DC, Croteau R (July 2005). "Mutational analysis of a monoterpene synthase reaction: altered catalysis through directed mutagenesis of (-)-pinene synthase from Abies grandis". Archives of Biochemistry and Biophysics. 439 (2): 222–33. doi:10.1016/j.abb.2005.05.017. PMID 15978541.
  10. ^ Savage TJ, Ichii H, Hume SD, Little DB, Croteau R (July 1995). "Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents". Archives of Biochemistry and Biophysics. 320 (2): 257–65. doi:10.1016/0003-9861(95)90008-x. PMID 7625832.
  11. ^ Phillips MA, Savage TJ, Croteau R (December 1999). "Monoterpene synthases of loblolly pine (Pinus taeda) produce pinene isomers and enantiomers". Archives of Biochemistry and Biophysics. 372 (1): 197–204. doi:10.1006/abbi.1999.1467. PMID 10562434.
  12. ^ McKay SA, Hunter WL, Godard KA, Wang SX, Martin DM, Bohlmann J, Plant AL (September 2003). "Insect attack and wounding induce traumatic resin duct development and gene expression of (-)-pinene synthase in Sitka spruce". Plant Physiology. 133 (1): 368–78. doi:10.1104/pp.103.022723. PMC 196613. PMID 12970502.

External links[edit]

Retrieved from "https://en.chped.com/w/index.php?title=(−)-beta-pinene_synthase&oldid=1227628917"