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Ligand (2Z,6Z)-farnesyl diphosphate

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

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Show Natural Substrate (5 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.142

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

758977

-

2.5.1.20

cis-farnesyl diphosphate + isopentenyl diphosphate = diphosphate + a polycis-polyprenyl diphosphate longer by one C5 unit

758969

-

4.2.3.50

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

706218

-

4.2.3.53

(2Z,6Z)-farnesyl diphosphate = (+)-endo-beta-bergamotene + diphosphate

706218

-

4.2.3.54

(2Z,6Z)-farnesyl diphosphate = (-)-endo-alpha-bergamotene + diphosphate

706218

-

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

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Show Natural Product (8 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.142

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

-

-

2.5.1.20

isopentenyl diphosphate + cis-1,4-polyisoprene = diphosphate + a poly-cis-polyprenyl diphosphate longer by one C5 unit

-

-

2.5.1.20

isopentenyl diphosphate + cis-1,4-polyisoprene = diphosphate + cis-1,4-polyisoprene + a poly-cis-polyprenyl diphosphate longer by one C5 unit

-

-

2.5.1.20

cis-farnesyl diphosphate + isopentenyl diphosphate = diphosphate + a polycis-polyprenyl diphosphate longer by one C5 unit

-

-

2.5.1.20

polycis-polyprenyl diphosphate + isopentenyl diphosphate = diphosphate + a polycis-polyprenyl diphosphate longer by one C5 unit

-

-

2.5.1.92

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

-

-

2.5.1.92

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

-

-

2.5.1.92

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

-

-

2.5.1.20

4 entries

2.5.1.92

3 entries

Substrate in Enzyme-catalyzed Reactions (9 results)

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Show Substrate (9 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.142

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

758977

-

2.5.1.142

dimethylallyl diphosphate + Z,Z-farnesyl diphosphate = ?

746178

-

2.5.1.142

2 entries

2.5.1.20

cis-farnesyl diphosphate + isopentenyl diphosphate = diphosphate + a polycis-polyprenyl diphosphate longer by one C5 unit

758969

-

4.2.3.142

(2Z,6Z)-farnesyl diphosphate = 7-epizingiberene + diphosphate

730612, 720937

-

4.2.3.50

(2Z,6Z)-farnesyl diphosphate = (+)-alpha-santalene + (+)-endo-beta-bergamotene + (-)-endo-alpha-bergamotene + (-)-exo-alpha-bergamotene + (-)-epi-beta-santalene

706218

-

4.2.3.50

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

706218

-

4.2.3.50

2 entries

4.2.3.53

(2Z,6Z)-farnesyl diphosphate = (+)-endo-beta-bergamotene + diphosphate

706218

-

4.2.3.54

(2Z,6Z)-farnesyl diphosphate = (-)-endo-alpha-bergamotene + diphosphate

706218

-

4.2.3.83

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

715604

-

Product in Enzyme-catalyzed Reactions (15 results)

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Show Product (15 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.5.1.142

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

-

-

2.5.1.20

isopentenyl diphosphate + (E,E)-farnesyl diphosphate + cis-1,4-polyisoprene = diphosphate + a poly-cis-polyprenyl diphosphate longer by one C5 unit

-

-

2.5.1.20

isopentenyl diphosphate + cis-1,4-polyisoprene = diphosphate + a poly-cis-polyprenyl diphosphate longer by one C5 unit

638729, 638728, 638726, 638724, 638731, 638725, 638737, 638732, 638727, 638734, 638733, , 638736, 638735, 638730

-

2.5.1.20

isopentenyl diphosphate + cis-1,4-polyisoprene = diphosphate + cis-1,4-polyisoprene + a poly-cis-polyprenyl diphosphate longer by one C5 unit

-

-

2.5.1.20

isopentenyl diphosphate + farnesyl diphosphate + cis-1,4-polyisoprene = diphosphate + a poly-cis-polyprenyl diphosphate longer by one C5 unit

, 638735, 638736, 638734

-

2.5.1.20

cis-farnesyl diphosphate + isopentenyl diphosphate = diphosphate + a polycis-polyprenyl diphosphate longer by one C5 unit

-

-

2.5.1.20

polycis-polyprenyl diphosphate + isopentenyl diphosphate = diphosphate + a polycis-polyprenyl diphosphate longer by one C5 unit

-

-

2.5.1.20

6 entries

2.5.1.28

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

-

-

2.5.1.29

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

-

-

2.5.1.68

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

-

-

2.5.1.92

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

-

-

2.5.1.92

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

-

-

2.5.1.92

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

-

-

2.5.1.92

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

-

-

2.5.1.92

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

-

-

2.5.1.92

5 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

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Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.5.1.142

0.0026

-

at pH 7.5 and 30°C

746178

4.2.3.142

0.29

-

pH not specified in the publication, temperature not specified in the publication

720937

K_M Value (2 results)

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Show KM Value (2 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.5.1.142

0.0229

-

at pH 7.5 and 30°C

746178

4.2.3.142

0.007

-

pH not specified in the publication, temperature not specified in the publication

720937

References & Links

Literature References (21)

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Show Reference (21 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

638724

16742418

The biosynthesis of rubber. Incorporation of isopentenyl pyrophosphate into purfied rubber particles by a soluble latex-serum enzyme

1966

McMullen, A.I.; McSweeney, G.P.

Biochem. J.

101

42-47

638725

-

Rubber transferase from hevea brasiliensis latex

1969

Archer, B.L.; Cockbain, E.G.

Methods Enzymol.

15

476-480

638726

2808388

Purification of a prenyltransferase that elongates cis-polyisoprene rubber from the latex of Hevea brasiliensis

1989

Light, D.R.; Dennis, M.S.

J. Biol. Chem.

264

18589-18597

638727

2808389

Rubber elongation by farnesyl pyrophosphate synthases involves a novel switch in enzyme stereospecificity

1989

Light, D.R.; Lazarus, R.A.; Dennis, M.S.

J. Biol. Chem.

264

18598-18607

638728

2681199

Rubber elongation factor from Hevea brasiliensis. Identification, characterization, and role in rubber biosynthesis

1989

Dennis, M.S.; Light, D.R.

J. Biol. Chem.

264

18608-18617

638729

2808390

Amino acid sequence of rubber elongation factor protein associated with rubber particles in Hevea latex

1989

Dennis, M.S.; Henzel, W.J.; Bell, J.; Kohr, W.; Light, D.R.

J. Biol. Chem.

264

18618-18626

638730

16663758

Isopentenyl pyrophosphate cis-1,4-polyisoprenyl transferase from guayule (Parthernium argentatum gray)

1984

Madhavan, S.; Benedict, C.R.

Plant Physiol.

75

908-913

638731

16667354

The Enzymatic Synthesis of Rubber Polymer in Parthenium argentatum Gray

1989

Benedict, C.R.; Madhavan, S.; Greenblatt, G.A.; Venkatachalam, K.V.; Foster, M.A.

Plant Physiol.

92

816-821

638732

8243473

The separate roles of plant cis and trans prenyl transferases in cis-1,4-polyisoprene biosynthesis

1993

Cornish, K.

Eur. J. Biochem.

218

267-271

638733

-

Immunoinhibition of rubber particle-bound cis-prenyl transferases in Ficus elastica and Parthenium argentatum

1994

Cornish, K.; Siler, D.J.; Grosjean, K.K.

Phytochemistry

35

1425-1428

638734

-

Identification of Parthenium argentatum rubber particle proteins immunoprecipitated by an antibody that specifically inhibits rubber transferase activity

1994

Siler, D.J.; Cornish, k.

Phytochemistry

36

623-627

638735

-

Characterization of cis-prenyl transferase activity localized in a buoyant fraction of rubber particles from Ficus elastica latex

1996

Cornish, K.; Siler, D.J.

Plant Physiol. Biochem.

34

377-384

638736

10889262

Identification of natural rubber and characterization of rubber biosynthetic activity in fig tree

2000

Kang, H.; Kang, M.Y.; Han, K.H.

Plant Physiol.

123

1133-1142

638737

-

Low night temperature-induced changes in photosynthesis and rubber accumulation in guayule (Parthenium argentatum Gray)

2000

Sundar, D.; Reddy, A.R.

Photosynthetica

38

421-427

706218

19155349

A novel pathway for sesquiterpene biosynthesis from Z,Z-farnesyl pyrophosphate in the wild tomato Solanum habrochaites

2009

Sallaud, C.; Rontein, D.; Onillon, S.; Jabe, F.; Duffé, P.; Giacalone, C.; Thoraval, S.; Escoffier, C.; Herbette, G.; Leonhardt, N.; Causse, M.; Tissier, A.

Plant Cell

21

301-317

715604

21454632

Sandalwood fragrance biosynthesis involves sesquiterpene synthases of both the terpene synthase (TPS)-a and TPS-b subfamilies, including santalene synthases

2011

Jones, C.G.; Moniodis, J.; Zulak, K.G.; Scaffidi, A.; Plummer, J.A.; Ghisalberti, E.L.; Barbour, E.L.; Bohlmann, J.

J. Biol. Chem.

286

17445-17454

720937

23169639

Haring, M.A. and Schuurink, R.C. Improved herbivore resistance in cultivated tomato with the sesquiterpene biosynthetic pathway from a wild relative

2012

Bleeker, P.M.; Mirabella, R.; Diergaarde, P.J.; Vandoorn, A.; Tissier, A.; Kant, M.R.; Prins, M.; de Vos, M.

Proc. Natl. Acad. Sci. USA

109

20124-20129

730612

22563774

Evolution of TPS20-related terpene synthases influences chemical diversity in the glandular trichomes of the wild tomato relative Solanum habrochaites

2012

Gonzales-Vigil, E.; Hufnagel, D.; Kim, J.; Last, R.; Barry, C.

Plant J.

71

921-935

746178

25786135

Biosynthesis of the diterpenoid lycosantalonol via nerylneryl diphosphate in Solanum lycopersicum

2015

Matsuba, Y.; Zi, J.; Jones, A.D.; Peters, R.J.; Pichersky, E.

PLoS ONE

10

e0119302

758969

30526485

The relationship between latex metabolism gene expression with rubber yield and related traits in Hevea brasiliensis

2018

Wu, C.; Lan, L.; Li, Y.; Nie, Z.; Zeng, R.

BMC Genomics

19

897

758977

32111159

Nerylneryl diphosphate is the precursor of serrulatane, viscidane and cembrane-type diterpenoids in Eremophila species

2020

Gericke, O.; Hansen, N.L.; Pedersen, G.B.; Kjaerulff, L.; Luo, D.; Staerk, D.; Moller, B.L.; Pateraki, I.; Heskes, A.M.

BMC Plant Biol.

20

91

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

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Show Links (1 entry)

ChEBI

PubChem

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