bornyl diphosphate synthase [EC:5.5.1.8]

PMID:12432096

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

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

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

[ag:AAC26017]

Isomerases;
Intramolecular lyases;
Intramolecular lyases (only sub-subclass identified to date)

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

geranyl diphosphate = (+)-bornyl diphosphate [RN:R02007]

R02007

geranyl diphosphate [CPD:C00341]

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].

EC 5.5.1.8 created 1984, modified 2012

1  [PMID:42356]

Croteau R, Karp F.

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 (1979) 512-22.

2  [PMID:2178556]

Croteau R, Gershenzon J, Wheeler CJ, Satterwhite DM

Biosynthesis of monoterpenes: stereochemistry of the coupled isomerization and cyclization of geranyl pyrophosphate to camphane and isocamphane monoterpenes.

Arch. Biochem. Biophys. 277 (1990) 374-81.

3  [PMID:3759972]

Croteau R, Satterwhite DM, Cane DE, Chang CC

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

J. Biol. Chem. 261 (1986) 13438-45.

4  [PMID:3997807]

Croteau R, Felton NM, Wheeler CJ

Stereochemistry at C-1 of geranyl pyrophosphate and neryl pyrophosphate in the cyclization to (+)- and (-)-bornyl pyrophosphate.

J. Biol. Chem. 260 (1985) 5956-62.

5  [PMID:4084562]

Croteau RB, Shaskus JJ, Renstrom B, Felton NM, Cane DE, Saito A, Chang C

Mechanism of the pyrophosphate migration in the enzymatic cyclization of geranyl  and linalyl pyrophosphates to (+)- and (-)-bornyl pyrophosphates.

Biochemistry. 24 (1985) 7077-85.

6  [PMID:7872777]

McGeady P, Croteau R

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

Arch. Biochem. Biophys. 317 (1995) 149-55.

7  [PMID:9614092]

Wise ML, Savage TJ, Katahira E, Croteau R.

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 (1998) 14891-9.

[ag:AAC26017]

8  [PMID:12432096]

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

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

Proc. Natl. Acad. Sci. U. S. A. 99 (2002) 15375-80.

[ag:AAC26017]

9  [PMID:12941302]

Peters RJ, Croteau RB

Alternative termination chemistries utilized by monoterpene cyclases: chimeric analysis of bornyl diphosphate, 1,8-cineole, and sabinene synthases.

Arch. Biochem. Biophys. 417 (2003) 203-11.