MetaCyc Reaction:

Superclasses: Reactions Classified By Conversion TypeSimple ReactionsChemical Reactions
Reactions Classified By SubstrateSmall-Molecule Reactions

EC Number:

Enzymes and Genes:

Salvia officinalis: (+)-bornyl diphosphate synthaseInferred from experiment: SBS

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

The direction shown, i.e. which substrates are on the left and right sides, 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 synthetase, (+)-bornylpyrophosphate cyclase, geranyl-diphosphate cyclase (ambiguous)

Standard Gibbs Free Energy (ΔrG in kcal/mol): -47.96Inferred 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

Gene-Reaction Schematic

Unification Links: KEGG:R02007, Rhea:18209

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

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


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

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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