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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Reaction: 5.5.1.8

Superclasses: Reactions Classified By Conversion Type Simple Reactions Chemical Reactions
Reactions Classified By Substrate Small-Molecule Reactions

EC Number: 5.5.1.8

Enzymes and Genes:
(+)-bornyl diphosphate synthase Inferred from experiment : SBS ( Salvia officinalis )

In Pathway: bornyl diphosphate biosynthesis , (+)-camphor biosynthesis

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the Enzyme Commission system.

Mass balance status: Balanced.

Enzyme Commission Primary Name: (+)-bornyl diphosphate synthase

Enzyme Commission Synonyms: bornyl pyrophosphate synthase, bornyl pyrophosphate synθse, (+)-bornylpyrophosphate cyclase, geranyl-diphosphate cyclase (ambiguous)

Standard Gibbs Free Energy (ΔrG in kcal/mol): -47.96 Inferred by computational analysis [Latendresse13]

Enzyme Commission Summary:
Requires Mg2+. The enzyme from Salvia officinalis (sage) can also use (3R)-linalyl diphosphate or more slowly neryl diphosphate in vitro [Croteau86]. The reaction proceeds via isomeration of geranyl diphosphate to (3R)-linalyl diphosphate. The oxygen and phosphorus directly linked to C-1 of geranyl diphosphate is also linked to C-2 of (+)-bornyl-diphosphate [Croteau86]. cf. EC 5.5.1.f [(-)-bornyl diphosphate synthase].

Citations: [Croteau79, Croteau90, Croteau85, Croteau85a, McGeady95, Wise98, Whittington02, Peters03]

Gene-Reaction Schematic: ?

Unification Links: KEGG:R02007 , Rhea:18209

Relationship Links: BRENDA:EC:5.5.1.8 , ENZYME:EC:5.5.1.8 , IUBMB-ExplorEnz:EC:5.5.1.8

Credits:
Revised 25-Jan-2012 by Caspi R , SRI International


References

Croteau79: Croteau R, Karp F (1979). "Biosynthesis of monoterpenes: preliminary characterization of bornyl pyrophosphate synthetase from sage (Salvia officinalis) and demonstration that Geranyl pyrophosphate is the preferred substrate for cyclization." Arch Biochem Biophys 198(2);512-22. PMID: 42356

Croteau85: Croteau R, Felton NM, Wheeler CJ (1985). "Stereochemistry at C-1 of geranyl pyrophosphate and neryl pyrophosphate in the cyclization to (+)- and (-)-bornyl pyrophosphate." J Biol Chem 260(10);5956-62. PMID: 3997807

Croteau85a: Croteau RB, Shaskus JJ, Renstrom B, Felton NM, Cane DE, Saito A, Chang C (1985). "Mechanism of the pyrophosphate migration in the enzymatic cyclization of geranyl and linalyl pyrophosphates to (+)- and (-)-bornyl pyrophosphates." Biochemistry 24(25);7077-85. PMID: 4084562

Croteau86: Croteau R, Satterwhite DM, Cane DE, Chang CC (1986). "Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of (+)- and (-)-linalyl pyrophosphate to (+)- and (-)-bornyl pyrophosphate." J Biol Chem 261(29);13438-45. PMID: 3759972

Croteau90: Croteau R, Gershenzon J, Wheeler CJ, Satterwhite DM (1990). "Biosynthesis of monoterpenes: stereochemistry of the coupled isomerization and cyclization of geranyl pyrophosphate to camphane and isocamphane monoterpenes." Arch Biochem Biophys 277(2);374-81. PMID: 2178556

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

McGeady95: McGeady P, Croteau R (1995). "Isolation and characterization of an active-site peptide from a monoterpene cyclase labeled with a mechanism-based inhibitor." Arch Biochem Biophys 317(1);149-55. PMID: 7872777

Peters03: Peters RJ, Croteau RB (2003). "Alternative termination chemistries utilized by monoterpene cyclases: chimeric analysis of bornyl diphosphate, 1,8-cineole, and sabinene synthases." Arch Biochem Biophys 417(2);203-11. PMID: 12941302

Whittington02: Whittington DA, Wise ML, Urbansky M, Coates RM, Croteau RB, Christianson DW (2002). "Bornyl diphosphate synthase: structure and strategy for carbocation manipulation by a terpenoid cyclase." Proc Natl Acad Sci U S A 99(24);15375-80. PMID: 12432096

Wise98: Wise ML, Savage TJ, Katahira E, Croteau R (1998). "Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase." J Biol Chem 273(24);14891-9. PMID: 9614092


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Dec 19, 2014, BIOCYC14B.