|Superclasses:||Reactions Classified By Conversion Type → Simple Reactions → Chemical Reactions|
|Reactions Classified By Substrate → Small-Molecule Reactions|
EC Number: 22.214.171.124
Enzymes and Genes:
|Salvia officinalis :||(+)-bornyl diphosphate synthase
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 [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].
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
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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