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Information on EC 4.2.3.82 - alpha-santalene synthase
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4.2.3.82 alpha-santalene synthaseIUBMB Comments
The enzyme synthesizes a mixture of sesquiterpenoids from (2E,6E)-farnesyl diphosphate. As well as (+)-alpha-santalene, (-)-beta-santalene and (-)-exo-alpha-bergamotene are formed with traces of (+)-epi-beta-santalene. See EC 4.2.3.83 [(-)-beta-santalene synthase], and EC 4.2.3.81 [(-)-exo-alpha-bergamotene synthase]. cf. EC 4.2.3.50 alpha-santalene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]
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Word Map
- 4.2.3.82
-
terpene
- sandalwood
-
sesquiterpene
-
santalols
- synthases
- santalum
- album
- mevalonate
- clausena
- lansium
- pyrophosphate
-
fed-batch
-
cyclization
- sesquiterpenoids
-
monoterpene
-
heartwood
-
unigenes
- sassy
-
bergamotene
- synthesis
The enzyme appears in viruses and cellular organisms
Synonyms
santalene synthase, sansyn, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
santalene synthase
SSy
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(2E,6E)-farnesyl diphosphate = (+)-alpha-santalene + diphosphate
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
-
-
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SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl diphosphate lyase (cyclizing, (+)-alpha-santalene-forming)
The enzyme synthesizes a mixture of sesquiterpenoids from (2E,6E)-farnesyl diphosphate. As well as (+)-alpha-santalene, (-)-beta-santalene and (-)-exo-alpha-bergamotene are formed with traces of (+)-epi-beta-santalene. See EC 4.2.3.83 [(-)-beta-santalene synthase], and EC 4.2.3.81 [(-)-exo-alpha-bergamotene synthase]. cf. EC 4.2.3.50 alpha-santalene synthase [(2Z,6Z)-farnesyl diphosphate cyclizing]
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 (2E,6E)-farnesyl diphosphate
(+)-alpha-santalene + trans-alpha-bergamotene + 2 diphosphate
-
amounts of the sesquiterpenes alpha-santalene and trans-alpha-bergamotene produced are,respectively,1.45 and0.177 mg/l
-
?
(2E,6E)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
when incubated in the presence of 10 mM Mg2+ the enzyme converts (2E,6E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
when incubated in the presence of 10 mM Mg2+ the enzyme converts (2Z,6Z)-farnesyl diphosphate into alpha-endo-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene and beta-santalene
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
when incubated in the presence of 10 mM Mg2+ the enzyme converts (2E,6E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
when incubated in the presence of 10 mM Mg2+ the enzyme converts (2E,6E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
-
-
?
(2E,6E)-farnesyl diphosphate
alpha-santalene + diphosphate
-
products are alpha-santalene, beta-, and epi-beta-santalene, exo-alpha-bergamotene, as well as traces of alpha- and beta-farnesene
-
?
(2E,6E)-farnesyl diphosphate
alpha-santalene + diphosphate
-
synthesis of a mixture of sesquiterpenes namely alpha-santalene, beta-santalene, epi-beta-santalene and alpha-bergamotene
-
?
(2E,6E)-farnesyl diphosphate
alpha-santalene + diphosphate
-
products are alpha-santalene, beta-, and epi-beta-santalene, alpha-exo-bergamotene, as well as traces of alpha- and beta-farnesene
-
?
(2E,6E)-farnesyl diphosphate
alpha-santalene + diphosphate
-
products are alpha-santalene, beta-, and epi-beta-santalene, alpha-exo-bergamotene, as well as traces of alpha- and beta-farnesene
-
?
additional information
?
-
the enzyme produces high amonuts of (+)-alpha-santalene from (2E,6E)-farnesyl diphosphate, and traces of (-)-exo-alpha-bergamotene
-
-
?
additional information
?
-
-
the enzyme produces high amonuts of (+)-alpha-santalene from (2E,6E)-farnesyl diphosphate, and traces of (-)-exo-alpha-bergamotene
-
-
?
additional information
?
-
the enzyme produces high amonuts of alpha-santalene from (2E,6E)-farnesyl diphosphate, and traces of (-)-exo-alpha-bergamotene. The enzyme assay is coupled to the inorganic diphosphatase (IPP1) from Saccharomyces cerevisiae. Compound identification and quantification by GC-MS and NMR analysis
-
-
?
additional information
?
-
-
the enzyme produces high amonuts of alpha-santalene from (2E,6E)-farnesyl diphosphate, and traces of (-)-exo-alpha-bergamotene. The enzyme assay is coupled to the inorganic diphosphatase (IPP1) from Saccharomyces cerevisiae. Compound identification and quantification by GC-MS and NMR analysis
-
-
?
additional information
?
-
Santalum album Ssy also accepts (2Z,6Z)-farnesyl diphosphate as substrate, producing a mixture of alpha-endo-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. With substrate geranyl diphosphate, products are linalool, geraniol, and terpineol along with traces of alpha-pinene and camphene. The product profile resulting from incubations of SaSSy with (E,E)-FPP resembles the authentic essential oil of Santalum album more closely than that of the (Z,Z)-FPP incubations
-
-
?
additional information
?
-
Santalum album Ssy also accepts (2Z,6Z)-farnesyl diphosphate as substrate, producing a mixture of alpha-endo-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. With substrate geranyl diphosphate, products are linalool, geraniol, and terpineol along with traces of alpha-pinene and camphene
-
-
?
additional information
?
-
the enzyme produces high amounts of (+)-alpha-santalene and (-)-beta-santalene, also (-)-exo-alpha-bergamotene, and low amounts of (-)-epi-beta-santalene from (2E,6E)-farnesyl diphosphate
-
-
?
additional information
?
-
the enzyme produces high amounts of (+)-alpha-santalene and (-)-beta-santalene, also (-)-exo-alpha-bergamotene, and low amounts of (-)-epi-beta-santalene from (2E,6E)-farnesyl diphosphate. The enzyme assay is coupled to the inorganic diphosphatase (IPP1) from Saccharomyces cerevisiae. Compound identification and quantification by GC-MS and NMR analysis
-
-
?
additional information
?
-
Santalum austrocaledonicum Ssy also accepts (2Z,6Z)-farnesyl diphosphate as substrate, producing a mixture of endo-alpha-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. With substrate geranyl diphosphate, products are linalool, geraniol, and terpineol along with traces of alpha-pinene and camphene
-
-
?
additional information
?
-
Santalum spicatum Ssy also accepts (2Z,6Z)-farnesyl diphosphate as substrate, producing a mixture of endo-alpha-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. With substrate geranyl diphosphate, products are linalool, geraniol, and terpineol along with traces of alpha-pinene and camphene
-
-
?
additional information
?
-
the enzyme produces (+)-alpha-santalene, (-)-beta-santalene, and (-)-exo-alpha-bergamotene, and traces of (-)-epi-beta-santalene from (2E,6E)-farnesyl diphosphate
-
-
?
additional information
?
-
the enzyme produces high amonuts of (+)-alpha-santalene and (-)-exo-alpha-bergamotene, also (-)-beta-santalene, and traces of (-)-epi-beta-santalene from (2E,6E)-farnesyl diphosphate. The enzyme assay is coupled to the inorganic diphosphatase (IPP1) from Saccharomyces cerevisiae. Compound identification and quantification by GC-MS and NMR analysis
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2E,6E)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
(+)-alpha-santalene + diphosphate
-
-
-
?
(2E,6E)-farnesyl diphosphate
alpha-santalene + diphosphate
-
products are alpha-santalene, beta-, and epi-beta-santalene, exo-alpha-bergamotene, as well as traces of alpha- and beta-farnesene
-
?
(2E,6E)-farnesyl diphosphate
alpha-santalene + diphosphate
-
products are alpha-santalene, beta-, and epi-beta-santalene, alpha-exo-bergamotene, as well as traces of alpha- and beta-farnesene
-
?
(2E,6E)-farnesyl diphosphate
alpha-santalene + diphosphate
-
products are alpha-santalene, beta-, and epi-beta-santalene, alpha-exo-bergamotene, as well as traces of alpha- and beta-farnesene
-
?
additional information
?
-
the enzyme produces high amonuts of (+)-alpha-santalene from (2E,6E)-farnesyl diphosphate, and traces of (-)-exo-alpha-bergamotene
-
-
?
additional information
?
-
-
the enzyme produces high amonuts of (+)-alpha-santalene from (2E,6E)-farnesyl diphosphate, and traces of (-)-exo-alpha-bergamotene
-
-
?
additional information
?
-
Santalum album Ssy also accepts (2Z,6Z)-farnesyl diphosphate as substrate, producing a mixture of alpha-endo-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. With substrate geranyl diphosphate, products are linalool, geraniol, and terpineol along with traces of alpha-pinene and camphene. The product profile resulting from incubations of SaSSy with (E,E)-FPP resembles the authentic essential oil of Santalum album more closely than that of the (Z,Z)-FPP incubations
-
-
?
additional information
?
-
the enzyme produces high amounts of (+)-alpha-santalene and (-)-beta-santalene, also (-)-exo-alpha-bergamotene, and low amounts of (-)-epi-beta-santalene from (2E,6E)-farnesyl diphosphate
-
-
?
additional information
?
-
Santalum austrocaledonicum Ssy also accepts (2Z,6Z)-farnesyl diphosphate as substrate, producing a mixture of endo-alpha-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. With substrate geranyl diphosphate, products are linalool, geraniol, and terpineol along with traces of alpha-pinene and camphene
-
-
?
additional information
?
-
Santalum spicatum Ssy also accepts (2Z,6Z)-farnesyl diphosphate as substrate, producing a mixture of endo-alpha-bergamotene, alpha-santalene, (Z)-beta-farnesene, epi-beta-santalene, and beta-santalene. With substrate geranyl diphosphate, products are linalool, geraniol, and terpineol along with traces of alpha-pinene and camphene
-
-
?
additional information
?
-
the enzyme produces (+)-alpha-santalene, (-)-beta-santalene, and (-)-exo-alpha-bergamotene, and traces of (-)-epi-beta-santalene from (2E,6E)-farnesyl diphosphate
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
Mn2+
Mg2+
when incubated in the presence of 10 mM Mg2+ the enzyme converts (E,E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
Mg2+
when incubated in the presence of 10 mM Mg2+ the enzyme converts (E,E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
Mg2+
when incubated in the presence of 10 mM Mg2+ the enzyme converts (E,E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
Mn2+
when incubated in the presence of 10 mM Mg2+ the enzyme converts (E,E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
Mn2+
incubation in presence of Mn2+ yields mainly alpha-exo-bergamotene
Mn2+
when incubated in the presence of 10 mM Mg2+ the enzyme converts (E,E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
Mn2+
incubation in presence of Mn2+ yields mainly exo-alpha-bergamotene
Mn2+
when incubated in the presence of 10 mM Mg2+ the enzyme converts (E,E)-farnesyl diphosphate into alpha-santalene, beta-santalene and epi-beta-santalene,alpha-exo-bergamotene, as well as traces of alpha-farnesene and beta-farnesene. Incubations with Mn2+ yields mainly alpha-exo-bergamotene
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0015
(2E,6E)-farnesyl diphosphate
recombinant His-tagged enzyme, pH 7.4, 37°C
0.002
(2E,6E)-farnesyl diphosphate
recombinant His-tagged enzyme, pH 7.4, 37°C
0.0027
(2E,6E)-farnesyl diphosphate
recombinant His-tagged enzyme, pH 7.4, 37°C
additional information
additional information
Michaelis-Menten kinetic analysis, overview. Kinetics are measured by IPP1 coupled colorimetric assay
-
additional information
additional information
Michaelis-Menten kinetic analysis, overview. Kinetics are measured by IPP1 coupled colorimetric assay
-
additional information
additional information
Michaelis-Menten kinetic analysis, overview. Kinetics are measured by IPP1 coupled colorimetric assay
-
additional information
additional information
-
Michaelis-Menten kinetic analysis, overview. Kinetics are measured by IPP1 coupled colorimetric assay
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.073
(2E,6E)-farnesyl diphosphate
recombinant His-tagged enzyme, pH 7.4, 37°C
0.075
(2E,6E)-farnesyl diphosphate
recombinant His-tagged enzyme, pH 7.4, 37°C
0.107
(2E,6E)-farnesyl diphosphate
recombinant His-tagged enzyme, pH 7.4, 37°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
27.04
(2E,6E)-farnesyl diphosphate
recombinant His-tagged enzyme, pH 7.4, 37°C
50
(2E,6E)-farnesyl diphosphate
recombinant His-tagged enzyme, pH 7.4, 37°C
53.3
(2E,6E)-farnesyl diphosphate
recombinant His-tagged enzyme, pH 7.4, 37°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.069
purified recombinant enzyme, substrate (2E,6E)-farnesyl diphosphate, pH 7.4, 37°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.4
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
37
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
expression in mature outer and transition zone is higher by 10% as compared to immature wood sample
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
the enzyme is involved in sandalwood oil biosynthesis
physiological function
the enzyme is involved in sandalwood oil biosynthesis
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). SPISY_SANSP
569
0
65407
Swiss-Prot
other Location (Reliability: 2)
SASY_SANAL
569
0
65163
Swiss-Prot
other Location (Reliability: 2)
SAUSY_SANAS
569
0
65268
Swiss-Prot
other Location (Reliability: 2)
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
66000
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by streptomycin sulfate and ammonium sulfate fractionation, desalting gel filtration, and anion exchange chromatography, followed by another step of ammonium sulfate fractionation and desalting gel filtration to near homogeneity
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) ickel affinity chromatography, dialysis, and ultrafiltration to near homogeneity
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) ickel affinity chromatography, dialysis, anion exchange chromatography, and gel filtration to near homogeneity
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
expression in Escherichia coli
heterologous expression of a His6-tagged protein in Escherichia coli
DNA and amino acid sequence determination and analysis, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
DNA and amino acid sequence determination and analysis, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
DNA and amino acid sequence determination and analysis, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
heterologous expression of a His6-tagged protein in Escherichia coli
heterologous expression of a His6-tagged protein in Escherichia coli
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
construction of a Saccharomyces cerevisiae strain capable of producing high levels of alpha-santalene through a rationally designed metabolic engineering approach.Optimal sesquiterpene production is obtained by modulating the expression of one of the keymetabolic steps of the mevalonate pathway, squalene synthase Erg9. Further optimization yields a final titer of 92 mg/l of alpha-santalene
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Jones, C.G.; Moniodis, J.; Zulak, K.G.; Scaffidi, A.; Plummer, J.A.; Ghisalberti, E.L.; Barbour, E.L.; 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
17445-17454
2011
Santalum album (E3W202), Santalum austrocaledonicum (E3W203), Santalum spicatum (E3W204)
brenda
Rani, A.; Ravikumar, P.; Reddy, M.D.; Kush, A.
Molecular regulation of santalol biosynthesis in Santalum album L.
Gene
527
642-648
2013
Santalum album (K7WTQ7), Santalum album
brenda
Scalcinati, G.; Knuf, C.; Partow, S.; Chen, Y.; Maury, J.; Schalk, M.; Daviet, L.; Nielsen, J.; Siewers, V.
Dynamic control of gene expression in Saccharomyces cerevisiae engineered for the production of plant sesquitepene alpha-santalene in a fed-batch mode
Metab. Eng.
14
91-103
2012
Clausena lansium (E5LLI1)
brenda
Hua, G.; Hu, Y.; Yang, C.; Liu, D.; Mao, Z.; Zhang, L.; Zhang, Y.
Characterization of santalene synthases using an inorganic pyrophosphatase coupled colorimetric assay
Anal. Biochem.
547
26-36
2018
Santalum album (E3W202), Santalum spicatum (E3W204), Clausena lansium (E5LLI1), Clausena lansium
brenda
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Release 2023.1 (January 2023)
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