print visible entries

print all entries

Ligand (2Z,6E)-farnesyl diphosphate

Basic Ligand Information

Molecular Structure

close all tables

open all tables

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (8 results)

top print hide

Show Natural Substrate (8 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.86

(2Z,6E)-farnesyl diphosphate + 7 isopentenyl diphosphate = 7 diphosphate + (2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E)-decaprenyl diphosphate

704266, 669077, 705121

-

2.5.1.86

(2Z,6E)-farnesyl diphosphate + 7 isopentenyl diphosphate = 7 diphosphate + trans,octacis-decaprenyl diphosphate

758676, 729897, 758604, 737596

-

2.5.1.86

(2Z,6E)-farnesyl diphosphate + isopentenyl diphosphate = diphosphate + trans,octacis-decaprenyl diphosphate

729897, 739101

-

2.5.1.86

3 entries

4.2.3.62

(2Z, 6E)-farnesyl diphosphate = (-)-gamma-cadinene + diphosphate

712565

-

4.2.3.70

(2Z,6E)-farnesyl diphosphate = patchoulol + diphosphate

746782

-

4.2.3.B17

(2Z,6E)-farnesyl diphosphate = (+)-2-epi-prezizaene + diphosphate

701441, 704204

-

4.2.3.B18

(2Z,6E)-farnesyl diphosphate = (-)-alpha-cedrene + diphosphate

701441, 704204

-

4.2.3.B19

(2Z,6E)-farnesyl diphosphate = (-)-beta-curcumene + diphosphate

701441, 704204

-

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

top print hide

Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.68

(E)-geranyl diphosphate + isopentenyl diphosphate = (2Z,6E)-farnesyl diphosphate + diphosphate

-

-

2.5.1.68

geranyl diphosphate + isopentenyl diphosphate = (2Z,6E)-farnesyl diphosphate + diphosphate

-

-

2.5.1.68

geranyl diphosphate + isopentenyl diphosphate = diphosphate + (2Z,6E)-farnesyl diphosphate

-

-

2.5.1.68

3 entries

Substrate in Enzyme-catalyzed Reactions (14 results)

top print hide

Show Substrate (14 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.86

(2Z,6E)-farnesyl diphosphate + 7 isopentenyl diphosphate = 7 diphosphate + (2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E)-decaprenyl diphosphate

669077, 705121, 704266

-

2.5.1.86

(2Z,6E)-farnesyl diphosphate + 7 isopentenyl diphosphate = 7 diphosphate + trans,octacis-decaprenyl diphosphate

758676, 729897, 758604, 737596, 721547

-

2.5.1.86

(2Z,6E)-farnesyl diphosphate + isopentenyl diphosphate = diphosphate + trans,octacis-decaprenyl diphosphate

729897, 739101

-

2.5.1.86

3 entries

2.5.1.88

(2Z,6E)-farnesyl diphosphate + n isopentenyl diphosphate = n diphosphate + trans,poly-cis-polyprenyl diphosphate

704741

-

4.2.3.128

(2Z,6E)-farnesyl diphosphate = beta-cubebene + diphosphate

714733

-

4.2.3.129

(2Z,6E)-farnesyl diphosphate = (+)-sativene + diphosphate

714733

-

4.2.3.55

(2Z,6E)-farnesyl diphosphate = (S)-beta-bisabolene + diphosphate

704432

-

4.2.3.6

(Z,E)-farnesyl diphosphate = ?

648335

-

4.2.3.62

(2Z, 6E)-farnesyl diphosphate = (-)-gamma-cadinene + diphosphate

712565

-

4.2.3.70

(2Z,6E)-farnesyl diphosphate = patchoulol + diphosphate

746782

-

4.2.3.9

(2Z,6E)-farnesyl diphosphate = (+)-2-epiprezizaene + (-)-alpha-cedrene + (-)-beta-curcumene + alpha-acoradiene + 4-epi-alpha-acoradiene + alpha-bisabolol + epi-alpha-bisabolol + nerolidol + (2Z,6E)-farnesol + diphosphate

704204

-

4.2.3.B17

(2Z,6E)-farnesyl diphosphate = (+)-2-epi-prezizaene + diphosphate

701441, 704204

-

4.2.3.B18

(2Z,6E)-farnesyl diphosphate = (-)-alpha-cedrene + diphosphate

701441, 704204

-

4.2.3.B19

(2Z,6E)-farnesyl diphosphate = (-)-beta-curcumene + diphosphate

701441, 704204

-

Product in Enzyme-catalyzed Reactions (3 results)

top print hide

Show Product (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.68

(E)-geranyl diphosphate + isopentenyl diphosphate = (2Z,6E)-farnesyl diphosphate + diphosphate

-

-

2.5.1.68

geranyl diphosphate + isopentenyl diphosphate = (2Z,6E)-farnesyl diphosphate + diphosphate

-

-

2.5.1.68

geranyl diphosphate + isopentenyl diphosphate = diphosphate + (2Z,6E)-farnesyl diphosphate

-

-

2.5.1.68

3 entries

Inhibitor in Enzyme-catalyzed Reactions (1 result)

top print hide

Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

5.3.3.2

-

2944

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (12 results)

top print hide

Show Turnover Number (12 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.5.1.86

11.5

-

pH 7.9, 37°C

704266

4.2.3.70

0.072

-

at pH 7.3 and 38°C

746782

4.2.3.9

0.095

-

in 200 mM Tris-HCl (pH 7.5), 40 mM MgCl2, at 22°C

704204

4.2.3.B17

0.077

-

pH 7.5, 22°C, promiscuous mutant enzyme M4

701441

4.2.3.B17

0.095

-

pH 7.5, 22°C

704204

4.2.3.B17

0.095

-

pH 7.5, 22°C, wild-type enzyme

701441

4.2.3.B18

0.077

-

pH 7.5, 22°C, promiscuous mutant enzyme M4

701441

4.2.3.B18

0.095

-

pH 7.5, 22°C

704204

4.2.3.B18

0.095

-

pH 7.5, 22°C, wild-type enzyme

701441

4.2.3.B19

0.077

-

pH 7.5, 22°C, promiscuous mutant enzyme M4

701441

4.2.3.B19

0.095

-

pH 7.5, 22°C

704204

4.2.3.B19

0.095

-

pH 7.5, 22°C, wild-type enzyme

701441

4.2.3.B17

3 entries

4.2.3.B18

3 entries

4.2.3.B19

3 entries

K_M Value (15 results)

top print hide

Show KM Value (15 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.5.1.31

0.0189

-

pH 8.5, 37°C

637474

2.5.1.31

0.305

-

pH 7.5, 35°C

637483

2.5.1.31

2 entries

2.5.1.86

0.29

-

pH 7.9, 37°C

704266

4.2.3.6

0.000036

-

pH 7.5

648335

4.2.3.70

0.008

-

at pH 7.3 and 38°C

746782

4.2.3.9

0.0143

-

in 200 mM Tris-HCl (pH 7.5), 40 mM MgCl2, at 22°C

704204

4.2.3.B17

0.00797

-

pH 7.5, 22°C, promiscuous mutant enzyme M4

701441

4.2.3.B17

0.01403

-

pH 7.5, 22°C

704204

4.2.3.B17

0.01403

-

pH 7.5, 22°C, wild-type enzyme

701441

4.2.3.B18

0.00797

-

pH 7.5, 22°C, promiscuous mutant enzyme M4

701441

4.2.3.B18

0.01403

-

pH 7.5, 22°C

704204

4.2.3.B18

0.01403

-

pH 7.5, 22°C, wild-type enzyme

701441

4.2.3.B19

0.00797

-

pH 7.5, 22°C, promiscuous mutant enzyme M4

701441

4.2.3.B19

0.01403

-

pH 7.5, 22°C

704204

4.2.3.B19

0.01403

-

pH 7.5, 22°C, wild-type enzyme

701441

4.2.3.B17

3 entries

4.2.3.B18

3 entries

4.2.3.B19

3 entries

References & Links

Literature References (20)

top print hide

Show Reference (20 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

2944

3740842

Isopentenyl pyrophosphate isomerase:dimetylallyl pyrophosphate isomerase: isolation from Claviceps sp. SD 58 and Comparison to the mammalian enzyme

1986

Bruenger, E.; Chayet, L.; Rilling, H.C.

Arch. Biochem. Biophys.

248

620-625

637474

6818223

Prenyltransferases of Bacillus subtilis: undecaprenyl pyrophosphate synthetase and geranylgeranyl pyrophosphate synthetase

1982

Takahashi, I.; Ogura, K.

J. Biochem.

92

1527-1537

637483

728420

Substrate specificity of undecaprenyl pyrophosphate synthetase from Lactobacillus plantarum

1978

Baba, T.; Allen, C.M.

Biochemistry

17

5598-5604

648335

7873526

Trichodiene synthase. Substrate specificity and inhibition

1995

Cane, D.E.; Yang, G.; Xue, Q.; Shim, J.H.

Biochemistry

34

2471-2479

669077

11004176

Polyprenyl phosphate biosynthesis in Mycobacterium tuberculosis and Mycobacterium smegmatis

2000

Crick, D.C.; Schulbach, M.C.; Zink, E.E.; Macchia, M.; Barontini, S.; Besra, G.S.; Brennan, P.J.

J. Bacteriol.

182

5771-5778

701441

20175559

Structural elucidation of cisoid and transoid cyclization pathways of a sesquiterpene synthase using 2-fluorofarnesyl diphosphates

2010

Noel, J.P.; Dellas, N.; Faraldos, J.A.; Zhao, M.; Hess, B.A.; Smentek, L.; Coates, R.M.; OMaille, P.E.

ACS Chem. Biol.

5

377-392

704204

20201526

Bisabolyl-derived sesquiterpenes from tobacco 5-epi-aristolochene synthase-catalyzed cyclization of (2Z,6E)-farnesyl diphosphate

2010

Faraldos, J.A.; OMaille, P.E.; Dellas, N.; Noel, J.P.; Coates, R.M.

J. Am. Chem. Soc.

132

4281-4289

704266

15516568

Decaprenyl diphosphate synthesis in Mycobacterium tuberculosis

2004

Kaur, D.; Brennan, P.J.; Crick, D.C.

J. Bacteriol.

186

7564-7570

704432

18524777

Protonation of a neutral (S)-beta-bisabolene intermediate is involved in (S)-beta-macrocarpene formation by the maize sesquiterpene synthases TPS6 and TPS11

2008

Köllner, T.G.; Schnee, C.; Li, S.; Svatos, A.; Schneider, B.; Gershenzon, J.; Degenhardt, J.

J. Biol. Chem.

283

20779-20788

704741

19447338

Cloning and functional analysis of cis-prenyltransferase from Thermobifida fusca

2009

Ambo, T.; Noike, M.; Kurokawa, H.; Koyama, T.

J. Biosci. Bioeng.

107

620-622

705121

18597781

The structural basis of chain length control in Rv1086

2008

Wang, W.; Dong, C.; McNeil, M.; Kaur, D.; Mahapatra, S.; Crick, D.C.; Naismith, J.H.

J. Mol. Biol.

381

129-140

712565

-

In vitro biosynthesis of cadinanes by cell-free extracts of cultured cells of Heteroscyphus planus

1997

Nabeta, K.; Fujita, M.; Komuro, K.; Katayama, K.; Takasawa, T.

J. Chem. Soc.

1

2065-2070

714733

20419721

Sesquiterpene synthases Cop4 and Cop6 from Coprinus cinereus: catalytic promiscuity and cyclization of farnesyl pyrophosphate geometric isomers

2010

Lopez-Gallego, F.; Agger, S.A.; Abate-Pella, D.; Distefano, M.D.; Schmidt-Dannert, C.

ChemBioChem

11

1093-1106

721547

23126257

Functional characterization of long-chain prenyl diphosphate synthases from tomato

2013

Jones, M.; Perez-Fons, L.; Robertson, F.; Bramley, P.; Fraser, P.

Biochem. J.

449

729-740

729897

24475925

Structure and inhibition of tuberculosinol synthase and decaprenyl diphosphate synthase from Mycobacterium tuberculosis

2014

Chan, H.C.; Feng, X.; Ko, T.P.; Huang, C.H.; Hu, Y.; Zheng, Y.; Bogue, S.; Nakano, C.; Hoshino, T.; Zhang, L.; Lv, P.; Liu, W.; Crick, D.C.; Liang, P.H.; Wang, A.H.; Oldfield, E.; Guo, R.T.

J. Am. Chem. Soc.

136

2892-2896

737596

24246678

In vitro and in vivo characterization of a novel insect decaprenyl diphosphate synthase: a two-major step catalytic mechanism is proposed

2013

Zhang, H.; Li, Z.X.

Biochem. Biophys. Res. Commun.

442

105-111

739101

24517327

Assessing the essentiality of the decaprenyl-phospho-D-arabinofuranose pathway in Mycobacterium tuberculosis using conditional mutants

2014

Kolly, G.S.; Boldrin, F.; Sala, C.; Dhar, N.; Hartkoorn, R.C.; Ventura, M.; Serafini, A.; McKinney, J.D.; Manganelli, R.; Cole, S.T.

Mol. Microbiol.

92

194-211

746782

26100386

Characterisation of a recombinant patchoulol synthase variant for biocatalytic production of terpenes

2015

Frister, T.; Hartwig, S.; Alemdar, S.; Schnatz, K.; Thoens, L.; Scheper, T.; Beutel, S.

Appl. Biochem. Biotechnol.

176

2185-2201

758604

30950820

Substrate-analogue complex structure of Mycobacterium tuberculosis decaprenyl diphosphate synthase

2019

Ko, T.P.; Xiao, X.; Guo, R.T.; Huang, J.W.; Liu, W.; Chen, C.C.

Acta Crystallogr. Sect. F

75

212-216

758676

27837315

Cloning and characterization of decaprenyl diphosphate synthase from three different fungi

2017

Moriyama, D.; Kaino, T.; Yajima, K.; Yanai, R.; Ikenaka, Y.; Hasegawa, J.; Washida, M.; Nanba, H.; Kawamukai, M.

Appl. Microbiol. Biotechnol.

101

1559-1571

Links to other databases for (2Z,6E)-farnesyl diphosphate

top print hide

Show Links (1 entry)

ChEBI

PubChem

-