KEGG   ENZYME: 5.5.1.22Help
Entry
EC 5.5.1.22                 Enzyme                                 

Name
(-)-bornyl diphosphate synthase;
bornyl pyrophosphate synthase (ambiguous);
bornyl pyrophosphate synthetase (ambiguous);
(-)-bornyl pyrophosphate cyclase;
bornyl diphosphate synthase;
geranyl-diphosphate cyclase (ambiguous);
(-)-bornyl-diphosphate lyase (decyclizing)
Class
Isomerases;
Intramolecular lyases;
Intramolecular lyases (only sub-subclass identified to date)
BRITE hierarchy
Sysname
(-)-bornyl-diphosphate lyase (ring-opening)
Reaction(IUBMB)
geranyl diphosphate = (-)-bornyl diphosphate [RN:R10509]
Reaction(KEGG)
Substrate
geranyl diphosphate [CPD:C00341]
Product
(-)-bornyl diphosphate [CPD:C20664]
Comment
Requires Mg2+. The enzyme from Tanacetum vulgare (tansy) can also use (3S)-linalyl diphosphate or more slowly neryl diphosphate in vitro. The reaction proceeds via isomeration of geranyl diphosphate to (3S)-linalyl diphosphate [3]. The oxygen and phosphorus originally linked to C-1 of geranyl diphosphate end up linked to C-2 of (-)-bornyl diphosphate [4]. cf. EC 5.5.1.8 (+)-bornyl diphosphate synthase.
History
EC 5.5.1.22 created 2012
Reference
1  [PMID:2178556]
  Authors
Croteau R, Gershenzon J, Wheeler CJ, Satterwhite DM
  Title
Biosynthesis of monoterpenes: stereochemistry of the coupled isomerization and cyclization of geranyl pyrophosphate to camphane and isocamphane monoterpenes.
  Journal
Arch. Biochem. Biophys. 277 (1990) 374-81.
Reference
2  [PMID:3970524]
  Authors
Croteau R, Shaskus J
  Title
Biosynthesis of monoterpenes: demonstration of a geranyl pyrophosphate:(-)-bornyl pyrophosphate cyclase in soluble enzyme preparations from tansy (Tanacetum vulgare).
  Journal
Arch. Biochem. Biophys. 236 (1985) 535-43.
Reference
3  [PMID:3997807]
  Authors
Croteau R, Felton NM, Wheeler CJ
  Title
Stereochemistry at C-1 of geranyl pyrophosphate and neryl pyrophosphate in the cyclization to (+)- and (-)-bornyl pyrophosphate.
  Journal
J. Biol. Chem. 260 (1985) 5956-62.
Reference
4  [PMID:4084562]
  Authors
Croteau RB, Shaskus JJ, Renstrom B, Felton NM, Cane DE, Saito A, Chang C
  Title
Mechanism of the pyrophosphate migration in the enzymatic cyclization of geranyl  and linalyl pyrophosphates to (+)- and (-)-bornyl pyrophosphates.
  Journal
Biochemistry. 24 (1985) 7077-85.
Reference
5  [PMID:9747540]
  Authors
Adam KP, Croteau R
  Title
Monoterpene biosynthesis in the liverwort Conocephalum conicum: demonstration of  sabinene synthase and bornyl diphosphate synthase.
  Journal
Phytochemistry. 49 (1998) 475-80.
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
CAS: 
110639-17-3

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