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Information on EC 4.2.3.20 - (R)-limonene synthase and Organism(s) Citrus limon and UniProt Accession Q8L5K3

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EC Tree
     4 Lyases
         4.2 Carbon-oxygen lyases
             4.2.3 Acting on phosphates
                4.2.3.20 (R)-limonene synthase
IUBMB Comments
Forms the first step of carvone biosynthesis in caraway. The enzyme from Carum carvi (caraway) seeds requires a divalent metal ion (preferably Mn2+) for catalysis. This enzyme occurs in Citrus, Carum (caraway) and Anethum (dill); (-)-limonene, however, is made in the fir, Abies, and mint, Mentha, by EC 4.2.3.16, (4S)-limonene synthase.
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This record set is specific for:
Citrus limon
UNIPROT: Q8L5K3
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The taxonomic range for the selected organisms is: Citrus limon
The enzyme appears in selected viruses and cellular organisms
Synonyms
d-limonene synthase, (+)-limonene synthase, citmtse1, cl(+)lims2, lalims, (+)-ls, cl(+)lims1, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
(+)-limonene synthase
-
(+)-limonene synthase
-
-
-
-
Cl(+)LIMS1
Cl(+)LIMS2
-
-
-
-
dLMS
-
-
-
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
geranyl diphosphate = (R)-limonene + diphosphate
show the reaction diagram
requires a divalent metal ion (preferably Mn2+) for catalysis
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
cyclization
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-(4R)-limonene-forming]
Forms the first step of carvone biosynthesis in caraway. The enzyme from Carum carvi (caraway) seeds requires a divalent metal ion (preferably Mn2+) for catalysis. This enzyme occurs in Citrus, Carum (caraway) and Anethum (dill); (-)-limonene, however, is made in the fir, Abies, and mint, Mentha, by EC 4.2.3.16, (4S)-limonene synthase.
CAS REGISTRY NUMBER
COMMENTARY hide
155807-65-1
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate
(+)-(R)-limonene + diphosphate
show the reaction diagram
geranyl diphosphate
(R)-limonene + diphosphate
show the reaction diagram
-
-
-
?
geranyl diphosphate
(+)-(R)-limonene + diphosphate
show the reaction diagram
-
product is exclusively R-(+)-limonene
?
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
geranyl diphosphate
(+)-(R)-limonene + diphosphate
show the reaction diagram
-
-
-
?
geranyl diphosphate
(R)-limonene + diphosphate
show the reaction diagram
-
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
geranyl diphosphate
substrate inhibition above 0.01 mM
K+
maximum inhibition above 100 mM
Mn2+
above 0.6 mM, activation below
geranyl diphosphate
substrate inhibition above 0.01 mM
K+
maximum inhibition above 100 mM
Mn2+
above 0.6 mM, activation below
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Mn2+
inhibition above 0.6 mM, activation below
Mn2+
inhibition above 0.6 mM, activation below
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0007
geranyl diphosphate
-
0.0007
geranyl diphosphate
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
peel of young developing fruit
Manually annotated by BRENDA team
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
RLC1_CITLI
606
0
70348
Swiss-Prot
Chloroplast (Reliability: 5)
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Saccharomyces cerevisiae strain AE9 K197G and Escherichia coli BL21 cells
limonene cyclase enzyme Cl(+)LIMS2 produced exclusively (+)-limonene as the major product of the enzymatic catalysis. In a chimeric enzyme, substitution of ClgammaTS domain III and domain IV by their counterparts from Cl(+)LIMS2 changed product specificity to that of Cl(+)LIMS2, (+)-limonene being the major product formed
-
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Lucker, J.; El Tamer, M.K.; Schwab, W.; Verstappen, F.W.; van der Plas, L.H.; Bouwmeester, H.J.; Verhoeven, H.A.
Monoterpene biosynthesis in lemon (Citrus limon). cDNA isolation and functional analysis of four monoterpene synthases
Eur. J. Biochem.
269
3160-3171
2000
Citrus limon (Q8L5K1), Citrus limon (Q8L5K3)
Manually annotated by BRENDA team
El Tamer, M.K.; Lucker, J.; Bosch, D.; Verhoeven, H.A.; Verstappen, F.W.A.; Schwab, W.; van Tunen, A.J.; Voragen, A.G.J.; de Maagd, R.A.; Bouwmeester, H.J.
Domain swapping of Citrus limon monoterpene synthases: impact on enzymatic activity and product specificity
Arch. Biochem. Biophys.
411
196-203
2003
Citrus limon
Manually annotated by BRENDA team
Jongedijk, E.; Cankar, K.; Ranzijn, J.; van der Krol, S.; Bouwmeester, H.; Beekwilder, J.
Capturing of the monoterpene olefin limonene produced in Saccharomyces cerevisiae
Yeast
32
159-171
2015
Citrus limon (Q8L5K3), Citrus limon
Manually annotated by BRENDA team