Information on EC 5.5.1.19 - lycopene beta-cyclase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea

EC NUMBER
COMMENTARY hide
5.5.1.19
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RECOMMENDED NAME
GeneOntology No.
lycopene beta-cyclase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
carotenoid psi-end group = carotenoid beta-end group
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
beta-carotene biosynthesis
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Biosynthesis of secondary metabolites
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Carotenoid biosynthesis
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lutein biosynthesis
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Metabolic pathways
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okenone biosynthesis
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carotenoid biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
carotenoid beta-end group lyase (decyclizing)
The enzyme is a non-redox flavoprotein, containing FADH2 that is used for stabilization of a transition state. Lycopene has a psi-end group at both ends. When acting on one end, the enzyme forms gamma-carotene. When acting on both ends it forms beta-carotene. It also acts on neurosporene to give beta-zeacarotene.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
Citrus sp.
gene Lycb-1
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Manually annotated by BRENDA team
inbred M01-3 cultivar with white mesocarp and orange mesocarp cultivar Homoka, gene CmLcyb1
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Manually annotated by BRENDA team
subsp. sativus, cv. Nantaise, gene DcLcyb1
UniProt
Manually annotated by BRENDA team
gene Lyc-beta
UniProt
Manually annotated by BRENDA team
single copy gene MpLcy-b
UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
gene crtY
UniProt
Manually annotated by BRENDA team
gene crtYB, encoding lycopene cyclase and phytoene synthase
UniProt
Manually annotated by BRENDA team
gene crtYB, encoding lycopene cyclase and phytoene synthase
UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
MpLCYb belongs to the LCYb1 (chloroplast-specific) family rather than to the LCYb2 (chromoplast-specific) family, hylogenetic tree
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
delta-carotene
alpha-carotene
show the reaction diagram
gamma-carotene
beta-carotene
show the reaction diagram
lycopene
beta-carotene
show the reaction diagram
lycopene
gamma-carotene
show the reaction diagram
neurosporene
beta-zeacarotene
show the reaction diagram
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?
additional information
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
delta-carotene
alpha-carotene
show the reaction diagram
gamma-carotene
beta-carotene
show the reaction diagram
lycopene
beta-carotene
show the reaction diagram
lycopene
gamma-carotene
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
FAD
the enzyme contains one noncovalently bound FAD that is essential for enzyme activity only in the presence of NADPH, which functions as the FAD reductant
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-(4-chlorophenylthio)-triethylamine
0.4 mM, complete inhibition
2-(4-methyl-phenoxy)-triethylamine
0.1 mM, complete inhibition
2-(4-methylphenoxy)tri-ethylamine hydrochloride
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2-(4-methylphenoxy)triethylamine hydrochloride
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NAD(P)H
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absolutely required for cyclization reaction. No hydrogen is transferred from NADPH, which is therefore not involved directly in the cyclization reaction, but must play an indirect role, e.g. as an allosteric activator
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.035
lycopene
pH 6.5, 30°C, recombinant enzyme
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.356
purified recombinant enzyme, pH 6.5, 30°C
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
calculated from sequence
6.73
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
storage root
Manually annotated by BRENDA team
expression levels are similar in males and females
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
43000
x * 43000, recombinant enzyme, SDS-PAGE
46125
x * 46125, calculated from sequence
56000
x * 56000, recombinant enzyme, SDS-PAGE
65630
x * 65630, sequence calculation
66000
1 * 66000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
1 * 66000, SDS-PAGE
additional information
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Q-Sepharose column chromatography, Affigel 501 gel filtration, Mono-P column chromatography, and Sephacryl gel filtration, and Superose 6 gel filtration
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by metal affinity chromatography to homogeneity
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli TOPO10 cells
expression in Escherichia coli
expression in Escherichia coli results in the simultaneous accumulation of alpha- beta-, delta-, and epsilon-carotene
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expression in Escherichia coli; expression in Escherichia coli
gene CmLcyb1, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic analysis, real time quantitative RT-PCR expression analysis
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gene crtY, DNA and amino acid sequence determination and analysis, expression of C-terminally His-tagged enzyme in Escherichia coli strain BL21(DE3) codon plus, 25°C is the optimum growth temperature for obtaining soluble lycopene cyclase in an active form
gene DcLcyb1, quantitative RT-PCR expression analysis, overexpression and heterologous complementation in enzyme-deficient Escherichia coli, transgenic expression of GFP-tagged enzyme in Nicotiana tabacum plants under control of ad35SCaMV promoter
gene Lcy-b, expression in tomato fruite under control of the 35S CaMV promoter in cotyledons via Agrobacterium tumefaciens-mediated transformation, the transgenic plants show increased lutein levels, quantitative real-time quantitative PCR expression analysis
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gene lcy-B, real-time quantitative RT-PCR expression analysis
gene Lyc-beta, DNA and amino acid sequence determination and analysis, sequence comparison and phylogenetic tree, expression in Escherichia coli strain BL21(DE3) leading to pigmentation of the transgenic bacteria, strongest at 28°C in the dark
gene Lycb-1, constitutive heterologous expression in Solanum lycopersicum fruits. In the transgenic line, the downstream alpha-branch metabolic fluxes are repressed during the three developmental stages while alpha-carotene content increases in the ripe stage, the beta-carotene level of transformant increases 4.1fold, and the total carotenoid content increases by 30% in the fruits. The constitutive expression of Lycb-1 affects a number of pathways including the synthesis of fatty acids, flavonoids and phenylpropanoids, the degradation of limonene and pinene, starch and sucrose metabolism and photosynthesis. Carotenoids contents in transgenic fruits at different stages of ripening, overview
Citrus sp.
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gene MpLCYb, DNA and amino acid sequence determination and analysis
recombinant expression of the gene in lycopene-producing Escherichia coli results in the accumulation of b-carotene in the cells
screening and cloning of gene crtYB, encoding lycopene cyclase and phytoene synthase, DNA and amino acid sequence determination and analysis, sequence comparisons
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enzyme is downregulated before fruit ripening through a tightly regulated physiological mechanism
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D127A
the mutation drastically reduces the lycopene cyclase activity of CCS up to 90%
D259A
the mutation drastically reduces the lycopene cyclase activity of CCS up to 90%
E128A
the mutation drastically reduces the lycopene cyclase activity of CCS up to 90%
E296A
the mutation reduces the lycopene cyclase activity of CCS
E332A
the mutation drastically reduces the lycopene cyclase activity of CCS up to 90%
down
the level of CrtL mRNA decreases at this stage of fruit ripening. Hence, the accumulation of lycopene in tomato fruits is due to a down-regulation of the lycopene cyclase gene that occurs at the breaker stage of fruit development
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
nutrition
Citrus sp.
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as tomato fruits are rich in beta-carotene precursors, there is a substantial interest in engineering carotenoid synthesis in tomato with a view to enhancing its beta-carotene content, through recombinant expression of the gene encoding lypoene beta-cyclase, for improving the human diet
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