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Information on EC 4.2.3.16 - (4S)-limonene synthase
for references in articles please use BRENDA:EC4.2.3.16
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EC Tree 4 Lyases
4.2 Carbon-oxygen lyases
4.2.3 Acting on phosphates
4.2.3.16 (4S)-limonene synthase
IUBMB Comments
A recombinant enzyme (also known as a monoterpene synthase or cyclase) from the grand fir (Abies grandis) requires Mn2+ and K+ for activity. Mg2+ is essentially ineffective as the divalent metal ion cofactor.
The enzyme appears in viruses and cellular organisms
- 4.2.3.16
-
monoterpene
- mentha
- spearmint
-
4s-limonene
-
perilla
- spicata
- frutescens
- gpp
- myrcene
- piperita
- peppermint
- beta-pinene
- valencene
-
linalyl
- synthesis
- agriculture
- industry
showSynonyms
limonene synthase, cstps1, (-)-limonene synthase, (4s)-limonene synthase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(-)-limonene synthase
EC 4.1.99.10
-
-
formerly
-
limonene synthase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate = (S)-limonene + diphosphate
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C-O bond cleavage
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
(4R)-carvone biosynthesis, fenchol biosynthesis II, menthol biosynthesis, monoterpene biosynthesis, oleoresin monoterpene volatiles biosynthesis, perillyl aldehyde biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase [cyclizing; (-)-(4S)-limonene-forming]
A recombinant enzyme (also known as a monoterpene synthase or cyclase) from the grand fir (Abies grandis) requires Mn2+ and K+ for activity. Mg2+ is essentially ineffective as the divalent metal ion cofactor.
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CAS REGISTRY NUMBER
COMMENTARY
110639-20-8
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate
(-)-limonene + diphosphate
Substrates: -
Products: 42% terpinolene, 18% (-)-alpha-pinene, 11% (-)-limonene, 10% (-)-beta-pinene plus several minor products
Products: 42% terpinolene, 18% (-)-alpha-pinene, 11% (-)-limonene, 10% (-)-beta-pinene plus several minor products
?
geranyl diphosphate
(4S)-limonene + diphosphate
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate
(S)-limonene + diphosphate
-
Substrates: important step in the biosynthesis of perillaldehyde
Products: -
Products: -
?
geranyl diphosphate
limonene + diphosphate
-
Substrates: step 3 and 4 of monoterpene biosynthesis, geranyl diphosphate is first ionized and isomerized to produce linalyl diphosphate, which either produces the acyclic monoterpenes or the alpha-terpinyl cation, the universal intermediate for cyclic monoterpenes and transformation of the parent structures to various derivatives
Products: limonene is a cyclic monoterpene, minor constituent of the spike lavender oil
Products: limonene is a cyclic monoterpene, minor constituent of the spike lavender oil
?
6,7-dihydrogeranyl diphosphate
?
-
Substrates: reaction yields only achiral, olefin products from 6,7-dehydrogeranyl diphosphate, no significant amounts of terpenols or homoterpenols are formed
Products: -
Products: -
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
Substrates: -
Products: small amounts of (-)-alpha-pinene, (-)-beta-pinene and beta-phellandrene as side products
Products: small amounts of (-)-alpha-pinene, (-)-beta-pinene and beta-phellandrene as side products
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
Substrates: induced by stem wounding, enhances resistance to insects
Products: small amounts of (-)-alpha-pinene, (-)-beta-pinene and beta-phellandrene as side products
Products: small amounts of (-)-alpha-pinene, (-)-beta-pinene and beta-phellandrene as side products
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
Mentha sp.
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
Mentha sp.
-
Substrates: -
Products: small amounts of (-)-alpha-pinene, (-)-beta-pinene and myrcene as side products
Products: small amounts of (-)-alpha-pinene, (-)-beta-pinene and myrcene as side products
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
Mentha sp.
-
Substrates: (3S)-linalyl diphosphate as intermediate
Products: -
Products: -
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
Mentha sp.
-
Substrates: essential for menthol production
Products: -
Products: -
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
-
Substrates: cyclization proceeds via preliminary isomerization to the bound tertiary intermediate 3S-linalyl diphosphate
Products: -
Products: -
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
Substrates: entire product set is derived in stereochemically consistent fashion via (-)-3S-linalyl diphosphate as intermediate
Products: -
Products: -
?
additional information
?
-
-
Substrates: overexpression of the LS does not alter the photosynthetic pigment content of spike lavender leaves
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate
(S)-limonene + diphosphate
-
Substrates: important step in the biosynthesis of perillaldehyde
Products: -
Products: -
?
geranyl diphosphate
limonene + diphosphate
-
Substrates: step 3 and 4 of monoterpene biosynthesis, geranyl diphosphate is first ionized and isomerized to produce linalyl diphosphate, which either produces the acyclic monoterpenes or the alpha-terpinyl cation, the universal intermediate for cyclic monoterpenes and transformation of the parent structures to various derivatives
Products: limonene is a cyclic monoterpene, minor constituent of the spike lavender oil
Products: limonene is a cyclic monoterpene, minor constituent of the spike lavender oil
?
additional information
?
-
-
Substrates: overexpression of the LS does not alter the photosynthetic pigment content of spike lavender leaves
Products: -
Products: -
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
Substrates: induced by stem wounding, enhances resistance to insects
Products: small amounts of (-)-alpha-pinene, (-)-beta-pinene and beta-phellandrene as side products
Products: small amounts of (-)-alpha-pinene, (-)-beta-pinene and beta-phellandrene as side products
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
Mentha sp.
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
Mentha sp.
-
Substrates: -
Products: small amounts of (-)-alpha-pinene, (-)-beta-pinene and myrcene as side products
Products: small amounts of (-)-alpha-pinene, (-)-beta-pinene and myrcene as side products
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
Mentha sp.
-
Substrates: essential for menthol production
Products: -
Products: -
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
-
Substrates: -
Products: -
Products: -
?
geranyl diphosphate
(-)-(4S)-limonene + diphosphate
-
Substrates: -
Products: -
Products: -
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
Mn2+
additional information
Mentha sp.
-
Ca2+, Cd2+, Co2+, Cu2+, Fe2+, Ni2+, Zn2+ activated less than 5%
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
6-cyclopropylidene-(3E)-methyl-hex-2-en-1-yl diphosphate
Mentha sp.
-
Ki: 0.0003 mM, irreversible covalent modification
diethyl dicarbonate
Mentha sp.
-
reversible with hydroxylamine, pretreatment with geranyl diphosphate and MnCl2 prevents inhibition
p-hydroxymercuribenzoate
Mentha sp.
-
pretreatment with geranyl diphosphate and MnCl2 prevents inhibition
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Acquired Immunodeficiency Syndrome
Inhibition of monoterpene cyclases by inert analogues of geranyl diphosphate and linalyl diphosphate.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0003
6-cyclopropylidene-(3E)-methyl-hex-2-en-1-yl diphosphate
Mentha sp.
-
irreversible covalent modification
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
increase in the expression of the spearmint LS cDNA at the different leaf developmental stages is accompanied with increases in the limonene content of transgenic spike lavender lines
additional information
-
leaves of transgenic plants contain increased limonene contents (more than 450% increase compared to controls) that correlates with the highest transcript accumulation of the LS gene.
additional information
-
the effect of the LS expression on oil composition decreases with leaf age as compared to the control
additional information
-
transgenic T0 spike lavender lines overexpressing MsLS show quantitative and qualitative alterations in their terpene profiles, particularly increased amounts of limonene as compared to controls (from 19.05% to 53.97% and from 12.50% to 83.33% in pooled leaves and flowers, respectively). The levels of other monoterpene pathway components are not consistently altered in either leaf or flower oils
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Mentha sp.
transgenic spike lavender plants expressing the limonene synthase gene from spearmint
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
the first two pairs of leaves from 40-day-old seedlings are used as primary explants for transformation
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
-
important step in the biosynthesis of perillaldehyde
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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). MTPS2_SANAL
576
0
65838
Swiss-Prot
other Location (Reliability: 5)
TPS6_MAIZE
548
0
63731
Swiss-Prot
other Location (Reliability: 3)
LIMNS_PICSI
634
0
72933
Swiss-Prot
Chloroplast (Reliability: 2)
TPS3_SOLLC
607
0
70652
Swiss-Prot
Chloroplast (Reliability: 3)
TPS1_CANSA
622
0
72385
Swiss-Prot
Chloroplast (Reliability: 1)
TPS11_MAIZE
548
0
63938
Swiss-Prot
other Location (Reliability: 3)
TPSDA_ABIGR
637
0
73478
Swiss-Prot
Chloroplast (Reliability: 2)
TPSDB_ABIGR
637
0
73273
Swiss-Prot
Chloroplast (Reliability: 2)
TPS26_MAIZE
627
0
70785
Swiss-Prot
Chloroplast (Reliability: 2)
ATERP_PINBN
626
0
71948
Swiss-Prot
Chloroplast (Reliability: 5)
G3LHT9_9APIA
163
0
18829
TrEMBL
other Location (Reliability: 2)
A0A0D3ML99_ELETR
583
0
67267
TrEMBL
Chloroplast (Reliability: 3)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
56000
73500
calculated MW of recombinant protein expressed in Escherichia coli
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
proteolytic modification
sequence contains a putative plastid targeting signal
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
crystal structure at 2.7 A resolution in two forms liganded to the substrate and intermediate analogs, 2-fluorogeranyl diphosphate and 2-fluorolinalyl diphosphate, respectively
-
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
exchange of the predicted helix D through F region gives rise to an (-)-limonene/(-)-alpha-pinene synthase product outcome
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
unstable in crude secretory cell extract, stable after DEAE-cellulose chromatography
Mentha sp.
-
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, stable for 1 week without loss of activity after DEAE-cellulose chromatography
Mentha sp.
-
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
partial
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
Agrobacterium-mediated transformation and regeneration of spike lavender is carried out and the transgenic Lavandula latifolia plants express the limonene synthase gene from Mentha spicata. Expression of limonene synthase in transgenic spike lavender results in an altered monoterpene composition in developing leaves, but does not consistently affect essential oil profile in pooled leaves and flowers of transgenic generation T0.
-
expressed in Escherichia coli
expression in Escherichia coli
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
significantly greater up-regulation in green form of the plant than in the red form of plants
-
the expression of (4S)-limonene synthase, 2-C-methyl-D-erythritol-2,4-cyclodiphosphate synthase Mds, (+)-pulegone reductase Pr, and (+)-menthofuran synthase Mfs do not show significant changes upon UV-B irradioation of field-grown and growth chamber plants
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
industry
-
limonene is an aromatic component in numerous products like beverages and cosmetics
synthesis
-
engineering of Echerichia coli with a heterologous mevalonate pathway and limonene synthase for production of limonene followed by coupling with a cytochrome P450,which specifically hydroxylates limonene to produce perillyl alcohol. A strain containing all mevalonate pathway genes in a single plasmid produces limonene at titers over 400 mg/l from glucose. Incorporation of a cytochrome P450 to hydroxylate limonene yields approximately 100mg/l of perilyl alcohol
agriculture
-
putative production of transgenic aromatic plants overexpressing monoterpene synthases
agriculture
-
UV-B irradiation differentially modulates the expression of genes involved in peppermint essential oil biogenesis and the content of UV-B absorbing flavonoids. Plants grown in field are better adapted to increasing UV-B irradiation than plants cultivated in growth chambers
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Croteau, R.; Alonso, W.R.; Koepp, A.E.; Shim, J.H.; Cane, D.E.
Irreversible inactivation of monoterpene cyclases by a mechanism-based inhibitor
Arch. Biochem. Biophys.
307
397-404
1993
Mentha sp.
brenda
Bohlmann, J.; Steele C.L.; Croteau, R.
Monoterpene synthases from grand fir (Abies grandis): cDNA isolation, characterization, and functional expression of myrcene synthase, (-)-(4S)-limonene synthase, and (-)-(1S,5S)-pinene synthase
J. Biol. Chem.
272
21784-21792
1997
Abies grandis (O22340), Abies grandis
brenda
Colby, S.M.; Alonso, W.R.; Katahira, E.J.; McGarvey, D.J.; Croteau, R.
4S-limonene synthase from the oil glands of spearmint (Mentha spicata): cDNA isolation, characterization, and bacterial expression of the catalytically active monoterpene cyclase
J. Biol. Chem.
268
23016-23024
1993
Mentha sp.
brenda
Yuba, A.; Yazaki, K.; Tabata, M.; Honda, G.; Croteau, R.
cDNA cloning, characterization, ana functional expression of 4S-(-)-limonene synthase from Perilla frutescens
Arch. Biochem. Biophys.
332
280-287
1996
Perilla frutescens
brenda
Alonso, W.R.; Rajaonarivony, J.I.M.; Gershenzon, J.; Croteau, R.
Purification of 4S-limonene synthase, a monoterpene cyclase from the glandular trichomes pf peppermint (Mentha x piperita) and spearmint (Mentha spicata)
J. Biol. Chem.
267
7582-7587
1992
Mentha sp.
brenda
Rajaonarivony, J.I.M.; Gershenzon, J.; Croteau, R.
Characterization and mechanism of (4S)-limonene synthase, a monoterpene cyclase from the glandular trichomes of peppermint (Mentha x piperita)
Arch. Biochem. Biophys.
296
49-57
1992
Mentha sp.
brenda
Alonso, W.R.; Crock, J.E.; Cotreau, R.
Production and characterization of polyclonal antibodies in rabbits to 4S-limonene synthase from spearmint (Mentha spicata)
Arch. Biochem. Biophys.
301
58-63
1993
Mentha sp.
brenda
Adam, K.P.; Crock, J.; Croteau, R.
Partial purification and characterization of a monoterpene cyclase, limonene synthase, from the liverwort Ricciocarpos natans
Arch. Biochem. Biophys.
332
352-356
1996
Ricciocarpos natans
brenda
Turner, G.; Gershenzon, J.; Nielson, E.E.; Froehlich, J.E.; Croteau, R.
Limonene synthase, the enzyme responsible for monoterpene biosynthesis in peppermint, is localized to leucoplasts of the oil gland secretory cells
Plant Physiol.
120
879-886
1999
Mentha sp.
brenda
Rajaonarivony, J.I.M.; Gershenzon, J.; Miyazaki, J.; Croteau, R.
Evidence for an essential histidine residue in 4S-limonene synthase and other terpene cyclases
Arch. Biochem. Biophys.
299
77-82
1992
Mentha sp.
brenda
Maruyama, T.; Ito, M.; Kiuchi, F.; Honda, G.
Molecular cloning, functional expression and characterization of D-limonene synthase from Schizonepeta tenuifolia
Biol. Pharm. Bull.
24
373-377
2001
Agastache rugosa
brenda
Schwab, W.; Williams, D.C.; Davis, E.M.; Croteau, R.
Mechanism of monoterpene cyclization: Stereochemical aspects of the transformation of noncyclizable substrate analogs by recombinant (-)-limonene synthase, (+)-bornyl diphosphate synthase, and (-)-pinene synthase
Arch. Biochem. Biophys.
392
123-136
2001
Mentha spicata
brenda
Katoh S.;Hyatt D.;Croteau R.
Altering product outcome in Abies grandis (-)-limonene synthase and (-)-limonene/(-)-alpha-pinene synthase by domain swapping and directed mutagenesis
Arch. Biochem. Biophys.
425
65-76
2004
Abies grandis
brenda
Schwab W.;Williams DC, Croteau R.
Mechanism of monoterpene cyclization: stereochemistry of the transformation of noncyclizable substrate analogs by recombinant (-)-limonene synthase, (+)-bornyl diphosphate synthase, and (-)-pinene synthase
J. Mol. Catal. B
19
415-421
2002
Mentha spicata
-
brenda
Martin, D.M.; Faeldt, J.; Bohlmann, J.
Functional characterization of nine Norway spruce TPS genes and evolution of gymnosperm terpene synthases of the TPS-d subfamily
Plant Physiol.
135
1908-1927
2004
Picea abies (Q675L1), Picea abies
brenda
Gunnewich, N.; Page, J.E.; Kollner, T.G.; Degenhardt, J.; Kutchan, T.M.
Functional expression and characterization of trichome-specific (-)-limonene synthase and (+)-alpha-pinene synthase from Cannabis sativa
Nat. Prod. Commun.
2
223-232
2007
Cannabis sativa
-
brenda
Byun-McKay, A.; Godard, K.A.; Toudefallah, M.; Martin, D.M.; Alfaro, R.; King, J.; Bohlmann, J.; Plant, A.L.
Wound-induced terpene synthase gene expression in Sitka spruce that exhibit resistance or susceptibility to attack by the white pine weevil
Plant Physiol.
140
1009-1021
2006
Picea sitchensis (Q20HU7), Picea sitchensis
brenda
Hyatt, D.C.; Youn, B.; Zhao, Y.; Santhamma, B.; Coates, R.M.; Croteau, R.B.; Kang, C.
Structure of limonene synthase, a simple model for terpenoid cyclase catalysis
Proc. Natl. Acad. Sci. USA
104
5360-5365
2007
Mentha spicata
brenda
Munoz-Bertomeu, J.; Ros, R.; Arrillaga, I.; Segura, J.
Expression of spearmint limonene synthase in transgenic spike lavender results in an altered monoterpene composition in developing leaves
Metab. Eng.
10
166-177
2008
Mentha spicata
brenda
Bohlmann, J.; Phillips, M.; Ramachandiran, V.; Katoh, S.; Croteau, R.
cDNA cloning, characterization, and functional expression of four new monoterpene synthase members of the Tpsd gene family from grand fir (Abies grandis)
Arch. Biochem. Biophys.
368
232-243
1999
Abies grandis (Q9M7D0)