KEGG ENZYME: 5.5.1.8

ENZYME: 5.5.1.8

Entry

EC 5.5.1.8                  Enzyme

Name

(+)-bornyl diphosphate synthase;
bornyl pyrophosphate synthase (ambiguous);
bornyl pyrophosphate synthetase (ambiguous);
(+)-bornylpyrophosphate cyclase;
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:R02007]

Reaction(KEGG)

R02007

Substrate

geranyl diphosphate [CPD:C00341]

Product

(+)-bornyl diphosphate [CPD:C03190]

Comment

Requires Mg2+. The enzyme from Salvia officinalis (sage) can also use (3R)-linalyl diphosphate or more slowly neryl diphosphate in vitro [3]. The reaction proceeds via isomeration of geranyl diphosphate to (3R)-linalyl diphosphate. The oxygen and phosphorus originally linked to C-1 of geranyl diphosphate end up linked to C-2 of (+)-bornyl diphosphate [3]. cf. EC 5.5.1.22 [(-)-bornyl diphosphate synthase].

History

EC 5.5.1.8 created 1984, modified 2012

Pathway

ec00902

Monoterpenoid biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K15098

bornyl diphosphate synthase

Reference

1 [PMID:42356]

Authors

Croteau R, Karp F.

Title

Biosynthesis of monoterpenes: preliminary characterization of bornyl pyrophosphate synthetase from sage (Salvia officinalis) and demonstration that Geranyl pyrophosphate is the preferred substrate for cyclization.

Journal

Arch Biochem Biophys 198:512-22 (1979)
DOI:10.1016/0003-9861(79)90526-5

Reference

2 [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

3 [PMID:3759972]

Authors

Croteau R, Satterwhite DM, Cane DE, Chang CC

Title

Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of (+)- and (-)-linalyl pyrophosphate to (+)- and (-)-bornyl pyrophosphate.

Journal

J Biol Chem 261:13438-45 (1986)

Reference

4 [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

5 [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

6 [PMID:7872777]

Authors

McGeady P, Croteau R

Title

Isolation and characterization of an active-site peptide from a monoterpene cyclase labeled with a mechanism-based inhibitor.

Journal

Arch Biochem Biophys 317:149-55 (1995)
DOI:10.1006/abbi.1995.1147

Reference

7 [PMID:9614092]

Authors

Wise ML, Savage TJ, Katahira E, Croteau R

Title

Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase.

Journal

J Biol Chem 273:14891-9 (1998)
DOI:10.1074/jbc.273.24.14891

Sequence

[ag:AAC26017]

Reference

8 [PMID:12432096]

Authors

Whittington DA, Wise ML, Urbansky M, Coates RM, Croteau RB, Christianson DW

Title

Bornyl diphosphate synthase: structure and strategy for carbocation manipulation by a terpenoid cyclase.

Journal

Proc Natl Acad Sci U S A 99:15375-80 (2002)
DOI:10.1073/pnas.232591099