(-)-Alfa-pinenska sintaza

(-)-Alfa-pinenska sintaza
Identifikatori
EC broj	4.2.3.119
IntEnz	IntEnz view
BRENDA	BRENDA entry
ExPASy	NiceZyme view
KEGG	KEGG entry
MetaCyc	metabolic pathway
PRIAM	profile
PDB	RCSB PDB PDBe PDBj PDBsum
Pretraga PMC articles PubMed articles NCBI Protein search

(-)-Alfa-pinenska sintaza (EC 4.2.3.119, (-)-alfa-pinen/(-)-kamken sintaza, (-)-alfa-pinen ciklaza) je enzim sa sistematskim imenom geranil-difosfat difosfat-lijaza (ciklizacija, formira (-)-alfa-pinen).^{[1][2][3][4][5][6][7][8][9][10][11][12][13][14]} Ovaj enzim katalizuje sledeću hemijsku reakciju

geranil difosfat ${\displaystyle \rightleftharpoons }$ (-)-alfa-pinen + difosfat

Ciklaza II iz Salvia officinalis formira jednake količine (-)-alfa-pinena, (-)-beta-pinena i (-)-kamfena.

Reference

1. Gambliel, H. and Croteau, R. (1984). „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. PMID 6693393. 
2. 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: 5383-5389. PMID 3314988. 
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: 10063-10071. PMID 3392006. 
4. 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: 15309-15315. PMID 2768265. 
5. 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: 488-496. PMID 8109979. 
6. 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: 477-486. PMID 12226526. 
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: 167-173. PMID 1731633. 
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. PMID 9268308. 
9. Bohlmann, J., Phillips, M., Ramachandiran, V., Katoh, S. and Croteau, R. (1999). „cDNA cloning, characterization, and functional expression of four new monoterpene synthase members of the Tpsd gene family from grand fir (Abies grandis)”. Arch. Biochem. Biophys. 368: 232-243. PMID 10441373. 
10. 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: 222-233. PMID 15978541. 
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: 197-204. PMID 10562434. 
12. Phillips, M.A., Wildung, M.R., Williams, D.C., Hyatt, D.C. and Croteau, R. (2003). „cDNA isolation, functional expression, and characterization of (+)-α-pinene synthase and (-)-α-pinene synthase from loblolly pine (Pinus taeda): stereocontrol in pinene biosynthesis”. Arch. Biochem. Biophys. 411: 267-276. PMID 12623076. 
13. 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: 368-378. PMID 12970502. 
14. Huber, D.P.W., Philippe, R.N., Godard, K.-A., Sturrock, R.N. and Bohlmann, J. (2005). „Characterization of four terpene synthase cDNAs from methyl jasmonate-induced Douglas-fir, Pseudotsuga menziesii”. Phytochemistry 66: 1427-1439. PMID 15921711. 

Literatura

• Nicholas C. Price, Lewis Stevens (1999). Fundamentals of Enzymology: The Cell and Molecular Biology of Catalytic Proteins (Third izd.). USA: Oxford University Press. ISBN 019850229X. 
• Eric J. Toone (2006). Advances in Enzymology and Related Areas of Molecular Biology, Protein Evolution (Volume 75 izd.). Wiley-Interscience. ISBN 0471205036. 
• Branden C, Tooze J.. Introduction to Protein Structure. New York, NY: Garland Publishing. ISBN: 0-8153-2305-0. 
• Irwin H. Segel. Enzyme Kinetics: Behavior and Analysis of Rapid Equilibrium and Steady-State Enzyme Systems (Book 44 izd.). Wiley Classics Library. ISBN 0471303097. 
• Robert A. Copeland (2013). Evaluation of Enzyme Inhibitors in Drug Discovery: A Guide for Medicinal Chemists and Pharmacologists (2nd izd.). Wiley-Interscience. ISBN 111848813X. 
• Gerhard Michal, Dietmar Schomburg (2012). Biochemical Pathways: An Atlas of Biochemistry and Molecular Biology (2nd izd.). Wiley. ISBN 0470146842. 

Vanjske veze

• MeSH (-)-alpha-pinene+synthase