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 277:374-81 (1990)
DOI:10.1016/0003-9861(90)90593-N
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 236:535-43 (1985)
DOI:10.1016/0003-9861(85)90656-3
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 260:5956-62 (1985)
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 24:7077-85 (1985)
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 49:475-80 (1998)
DOI:10.1016/S0031-9422(97)00741-3
Other DBs
ExplorEnz - The Enzyme Database: 5.5.1.22
IUBMB Enzyme Nomenclature: 5.5.1.22
ExPASy - ENZYME nomenclature database: 5.5.1.22
BRENDA, the Enzyme Database: 5.5.1.22
CAS: 110639-17-3

DBGET integrated database retrieval system