KEGG ENZYME: 5.5.1.22

ENZYME: 5.5.1.22

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)

Sysname

(-)-bornyl-diphosphate lyase (ring-opening)

Reaction(IUBMB)

geranyl diphosphate = (-)-bornyl diphosphate [RN:R10509]

Reaction(KEGG)

R10509

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)
DOI:10.1021/bi00346a009

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

All links

Chemical substance (2)   
   KEGG COMPOUND (2)   
Chemical reaction (2)   
   KEGG REACTION (1)   
   KEGG RCLASS (1)   
All databases (4)   

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