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4.2.3.50

Accepted name:

(+)-α-santalene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]

Reaction:

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

For diagram of santalene and bergamotene biosynthesis, click here

Other name(s):

SBS (ambiguous)

Systematic name:

(2Z,6Z)-farnesyl diphosphate lyase [cyclizing; (+)-α-santalene-forming]

Comments:

The enzyme synthesizes a mixture of sesquiterpenoids from (2Z,6Z)-farnesyl diphosphate. Following dephosphorylation of (2Z,6Z)-farnesyl diphosphate, the (2Z,6Z)-farnesyl carbocation is converted to either the (6R)- or the (6S)-bisabolyl cations depending on the stereochemistry of the 6,1 closure. The (6R)-bisabolyl cation will then lead to the formation of (+)-α-santalene (EC 4.2.3.50), while the (6S)-bisabolyl cation will give rise to (+)-endo-β-bergamotene (see EC 4.2.3.53) as well as (-)-endo-α-bergamotene (see EC 4.2.3.54). Small amounts of (-)-epi-β-santalene are also formed from the (6R)-bisabolyl cation and small amounts of (-)-exo-α-bergamotene are formed from the (6S)-bisabolyl cation [1].

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

Sallaud, C., Rontein, D., Onillon, S., Jabes, F., Duffe, P., Giacalone, C., Thoraval, S., Escoffier, C., Herbette, G., Leonhardt, N., Causse, M. and Tissier, A. A novel pathway for sesquiterpene biosynthesis from Z,Z-farnesyl pyrophosphate in the wild tomato Solanum habrochaites. Plant Cell 21 (2009) 301–317. [DOI] [PMID: 19155349]

[EC 4.2.3.50 created 2010]

4.2.3.53

Accepted name:

(+)-endo-β-bergamotene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]

Reaction:

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

For diagram of santalene and bergamotene biosynthesis, click here

Other name(s):

SBS (ambiguous)

Systematic name:

(2Z,6Z)-farnesyl diphosphate lyase (cyclizing; (+)-endo-β-bergamotene-forming)

Comments:

The enzyme synthesizes a mixture of sesquiterpenoids from (2Z,6Z)-farnesyl diphosphate. Following dephosphorylation of (2Z,6Z)-farnesyl diphosphate, the (2Z,6Z)-farnesyl carbocation is converted to either the (6R)- or the (6S)-bisabolyl cations depending on the stereochemistry of the 6,1 closure. The (6R)-bisabolyl cation will then lead to the formation of (+)-α-santalene (see EC 4.2.3.50), while the (6S)-bisabolyl cation will give rise to (-)-endo-α-bergamotene (see EC 4.2.3.54), as well as (+)-endo-β-bergamotene. Small amounts of (-)-epi-β-santalene are also formed from the (6R)-bisabolyl cation and small amounts of (-)-exo-α-bergamotene are formed from the (6S)-bisabolyl cation [1].

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

[EC 4.2.3.53 created 2010]

4.2.3.54

Accepted name:

(-)-endo-α-bergamotene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]

Reaction:

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

For diagram of santalene and bergamotene biosynthesis, click here

Other name(s):

SBS (ambiguous)

Systematic name:

(2Z,6Z)-farnesyl diphosphate lyase [cyclizing; (-)-endo-α-bergamotene-forming]

Comments:

The enzyme synthesizes a mixture of sesquiterpenoids from (2Z,6Z)-farnesyl diphosphate. Following dephosphorylation of (2Z,6Z)-farnesyl diphosphate, the (2Z,6Z)-farnesyl carbocation is converted to either the (6R)- or the (6S)-bisabolyl cations depending on the stereochemistry of the 6,1 closure. The (6R)-bisabolyl cation will then lead to the formation of (+)-α-santalene (see EC 4.2.3.50), while the (6S)-bisabolyl cation will give rise to (+)-endo-β-bergamotene (EC 4.2.3.53) as well as (-)-endo-α-bergamotene. Small amounts of (-)-epi-β-santalene are also formed from the (6R)-bisabolyl cation and small amounts of (-)-exo-α-bergamotene are formed from the (6S)-bisabolyl cation [1].

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

[EC 4.2.3.54 created 2010]

4.2.3.81

Accepted name:

exo-α-bergamotene synthase

Reaction:

(2E,6E)-farnesyl diphosphate = (-)-exo-α-bergamotene + diphosphate

For diagram of santalene and bergamotene biosynthesis, click here

Glossary:

(-)-exo-α-bergamotene = (-)-trans-α-bergamotene = (1S,5S,6R)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene

Other name(s):

trans-α-bergamotene synthase; LaBERS (gene name)

Systematic name:

(2E,6E)-farnesyl diphosphate lyase (cyclizing, (-)-exo-α-bergamotene-forming)

Comments:

The enzyme synthesizes a mixture of sesquiterpenoids from (2E,6E)-farnesyl diphosphate. As well as (-)-exo-α-bergamotene (74%) there were (E)-nerolidol (10%), (Z)-α-bisabolene (6%), (E)-β-farnesene (5%) and β-sesquiphellandrene (1%).

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB

References:

1.	Schnee, C., Kollner, T.G., Held, M., Turlings, T.C., Gershenzon, J. and Degenhardt, J. The products of a single maize sesquiterpene synthase form a volatile defense signal that attracts natural enemies of maize herbivores. Proc. Natl. Acad. Sci. USA 103 (2006) 1129–1134. [DOI] [PMID: 16418295]
2.	Landmann, C., Fink, B., Festner, M., Dregus, M., Engel, K.H. and Schwab, W. Cloning and functional characterization of three terpene synthases from lavender (Lavandula angustifolia). Arch. Biochem. Biophys. 465 (2007) 417–429. [DOI] [PMID: 17662687]

[EC 4.2.3.81 created 2011]

4.2.3.82

Accepted name:

α-santalene synthase

Reaction:

(2E,6E)-farnesyl diphosphate = (+)-α-santalene + diphosphate

For diagram of santalene and bergamotene biosynthesis, click here

Glossary:

(-)-exo-α-bergamotene = (-)-trans-α-bergamotene = (1S,5S,6R)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene

Systematic name:

(2E,6E)-farnesyl diphosphate lyase (cyclizing, (+)-α-santalene-forming)

Comments:

The enzyme synthesizes a mixture of sesquiterpenoids from (2E,6E)-farnesyl diphosphate. As well as (+)-α-santalene, (-)-β-santalene and (-)-exo-α-bergamotene are formed with traces of (+)-epi-β-santalene. See EC 4.2.3.83 [(-)-β-santalene synthase], and EC 4.2.3.81 [(-)-exo-α-bergamotene synthase]. cf. EC 4.2.3.50 α-santalene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB

References:

Jones, C.G., Moniodis, J., Zulak, K.G., Scaffidi, A., Plummer, J.A., Ghisalberti, E.L., Barbour, E.L. and Bohlmann, J. Sandalwood fragrance biosynthesis involves sesquiterpene synthases of both the terpene synthase (TPS)-a and TPS-b subfamilies, including santalene synthases. J. Biol. Chem. 286 (2011) 17445–17454. [DOI] [PMID: 21454632]

[EC 4.2.3.82 created 2011]

4.2.3.83

Accepted name:

β-santalene synthase

Reaction:

(2E,6E)-farnesyl diphosphate = (-)-β-santalene + diphosphate

For diagram of santalene and bergamotene biosynthesis, click here

Glossary:

(-)-exo-α-bergamotene = (-)-trans-α-bergamotene = (1S,5S,6R)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene

Systematic name:

(2E,6E)-farnesyl diphosphate lyase (cyclizing, (-)-β-santalene-forming)

Comments:

The enzyme synthesizes a mixture of sesquiterpenoids from (2E,6E)-farnesyl diphosphate. As well as (-)-β-santalene (+)-α-santalene and (-)-exo-α-bergamotene are formed with traces of (+)-epi-β-santalene. See EC 4.2.3.82 [(+)-α-santalene synthase], and EC 4.2.3.81 [(-)-exo-α-bergamotene synthase].

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB

References:

[EC 4.2.3.83 created 2011]