Information on EC 1.14.13.81 - magnesium-protoporphyrin IX monomethyl ester (oxidative) cyclase

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

EC NUMBER
COMMENTARY hide
1.14.13.81
-
RECOMMENDED NAME
GeneOntology No.
magnesium-protoporphyrin IX monomethyl ester (oxidative) cyclase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = 131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + 2 H2O
show the reaction diagram
(1b)
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-
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131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = 3,8-divinyl protochlorophyllide a + NADP+ + 2 H2O
show the reaction diagram
(1c)
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-
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magnesium-protoporphyrin IX 13-monomethyl ester + 3 NADPH + 3 H+ + 3 O2 = 3,8-divinyl protochlorophyllide a + 3 NADP+ + 5 H2O
show the reaction diagram
overall reaction
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-
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magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2 = 131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O
show the reaction diagram
(1a)
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-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
cyclization
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oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
chlorophyll metabolism
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Porphyrin and chlorophyll metabolism
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Metabolic pathways
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
magnesium-protoporphyrin-IX 13-monomethyl ester,NADPH:oxygen oxidoreductase (hydroxylating)
Requires Fe(II) for activity. The enzyme participates in the biosynthesis of chlorophyllide a in aerobic organisms. The same transformation is achieved in anaerobic organisms by EC 1.21.98.3, anaerobic magnesium-protoporphyrin IX monomethyl ester cyclase. Some facultative phototrophic bacteria, such as Rubrivivax gelatinosus, possess both enzymes.
CAS REGISTRY NUMBER
COMMENTARY hide
92353-62-3
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
green phototrophic bacterium
UniProt
Manually annotated by BRENDA team
green phototrophic bacterium
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
gammaproteobacteria NOR51-B
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-
-
Manually annotated by BRENDA team
first MPEC gene identification in cDNA library (PNZIP)
UniProt
Manually annotated by BRENDA team
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Q28W44
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Methylobacterium extorquens ATCC 14718 / DSM 1338 / JCM 2805 / NCIMB 9133 / AM1
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UniProt
Manually annotated by BRENDA team
-
A0A0K1L5Y4
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
gene bchE
-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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A4EGS5, A6FPX8
UniProt
Manually annotated by BRENDA team
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A6FPX8
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
spinach
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
wheat
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
metabolism
physiological function
additional information
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protein YGL8 has the dual functions in chlorophyll biosynthesis: one as a catalytic subunit of MgPME cyclase, the other as a core component of FLU-YGL8-LCAA-POR complex in chlorophyll biosynthesis, physical interaction between YGL8 and a rice chloroplast protein, low chlorophyll accumulation A (OsLCAA). YGL8 also interacts with the other two rice chloroplast proteins, viz. fluorescent (OsFLU1) and NADPH:protochlorophyllide oxidoreductase (OsPORB)
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + O2
131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O
show the reaction diagram
131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2
divinylprotochlorophyllide + NADP+ + 2 H2O
show the reaction diagram
magnesium-mesoporphyrin IX + NADPH + O2
diethyl protochlorophyllide + NADP+ + H2O
show the reaction diagram
-
-
-
?
magnesium-protoporphyrin IX + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
magnesium-protoporphyrin IX 13-monomethyl ester + 3 NADPH + 3 H+ + 3 O2
3,8-divinyl protochlorophyllide a + 3 NADP+ + 5 H2O
show the reaction diagram
magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + O2
131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O
show the reaction diagram
magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + O2
magnesium-protochlorophyllide + NADP+ + H2O
show the reaction diagram
magnesium-protoporphyrin IX monomethyl ester + NADPH + H+ + O2
protochlorophyllide a + NADP+ + H2O
show the reaction diagram
magnesium-protoporphyrin IX monomethyl ester + NADPH + O2
magnesium-divinyl-protochlorophyllide + NADP+ + H2O
show the reaction diagram
magnesium-protoporphyrin monomethyl ester + NADPH + H+ + O2
magnesium-divinyl-protochlorophyllide a + NADP+ + H2O
show the reaction diagram
Mg-protoporphyrin IX monomethyl ester + O2 + NADPH + H+
Mg-protochlorophyllide + NADP+ + H2O
show the reaction diagram
additional information
?
-
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
131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + O2
131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O
show the reaction diagram
131-oxo-magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + H+ + O2
divinylprotochlorophyllide + NADP+ + 2 H2O
show the reaction diagram
magnesium-protoporphyrin IX 13-monomethyl ester + 3 NADPH + 3 H+ + 3 O2
3,8-divinyl protochlorophyllide a + 3 NADP+ + 5 H2O
show the reaction diagram
magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + O2
131-hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester + NADP+ + H2O
show the reaction diagram
magnesium-protoporphyrin IX 13-monomethyl ester + NADPH + O2
magnesium-protochlorophyllide + NADP+ + H2O
show the reaction diagram
Q5EFU4
the enzyme is involved in the chlorophyll biosynthesis
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ir
magnesium-protoporphyrin IX monomethyl ester + NADPH + H+ + O2
protochlorophyllide a + NADP+ + H2O
show the reaction diagram
magnesium-protoporphyrin IX monomethyl ester + NADPH + O2
magnesium-divinyl-protochlorophyllide + NADP+ + H2O
show the reaction diagram
magnesium-protoporphyrin monomethyl ester + NADPH + H+ + O2
magnesium-divinyl-protochlorophyllide a + NADP+ + H2O
show the reaction diagram
Mg-protoporphyrin IX monomethyl ester + O2 + NADPH + H+
Mg-protochlorophyllide + NADP+ + H2O
show the reaction diagram
-
disruption of the bchE gene leads to accumulation of Mg-protoporphyrin IX monomethyl ester and the divinyl form of Mg-protoporphyrin IX monomethyl ester
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?
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
heme
high probability for binuclear iron motif is proposed by sequence alignment, and a significant iron amount in the chlorosome fraction cannot be assigned to other chlorosome proteins
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
FeSO4
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when added with 1,10-phenanthroline
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
2,2'-bipyridyl
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chelation of Fe2+
2-mercaptoethanol
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24% inhibition at 1 mM
4-chloromercuribenzene sulfonate
4-chloromercuribenzoate
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complete inhibition at 0.4 mM
amitrole
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0.1 and 1 mM
benzoquinone
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dithiothreitol
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50% inhibition at 1 mM
EDTA
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chelation of Fe3+
imazalil
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0.1 mM
methyl viologen
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at micromolar concentrations
methylene blue
N-ethylmaleimide
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90% inhibition at 5 mM
phenazine methosulfate
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at micromolar concentrations
quinol
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ascorbate
ATP
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requirement for reconstituted system
catalase
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isoascorbate
S-adenosyl-L-methionine
XanL
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required by the enzyme, found associated with the membrane and protein Ycf54
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Ycf54
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Ycf54 protein
the Ycf54 protein forms a complex with the component of the oxidative cyclase, Sll1214 (CycI, gene slr1780). Partial inactivation of the ycf54 gene leads to Chl deficiency in cyanobacteria and plants, and the complete deletion of the ycf54 gene in the cyanobacterium Synechocystis 6803 results accumulation of huge concentrations of the cyclase substrate MgPME together with 3-formyl MgPME, in the DELTAycf54 strain. The Ycf54 protein is important, but not essential, for activity of the oxidative cyclase
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0000085
average wild-type activity in chloroplasts
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
9
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supernatant protein
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
9.1
A0A0K1L5Y4
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
specifically expressed in photosynthetic active cells
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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soluble cell extract from cucumbers
Manually annotated by BRENDA team
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40000
SDS-PAGE, trypsin-digested
43000
calculted from predicted 370 amino acid residue sequence, 1402 bp, PNZIP from Pharbitis nil
45000
calculated from the acsF gene sequence encoding 375 amino acid residues
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
heterodimer
additional information
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-15°C, 30% loss of activity in supernatant, 70% loss of activity in pellet after 7 days
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cells are centrifuged, sonicated, cell debris removed by centrifugation, membrane fraction separated from the soluble fraction by ultracentrifugation, chlorosome fractioned by sucrose density gradient (15-45%), for SDS-PAGE chlorosome fraction is incubated in methanol, centrifuged, the pellet containing the chlorosome envelop is subjected to SDS-PAGE, protein identification by MALDI-TOF and liquid chromatography-tandem mass spectrometry
partial, soluble fraction
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partially by chloroplast supernatant and membrane preparation of wild-type and recombinant mutant plants
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amin acid sequence determination and analysis, sequence comparisons
gene CHL27, encoding the CHLH subunit of enzyme Mg protoporphyrin monomethylester cyclase
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gene OsCRD1, encoding a putative subunit of enzyme MPEC, is a single-copy gene in rice, sequence comparisons, quantitative real-time RT-PCR enzyme expression analysis
gene PeMPEC, DNA and amino acid sequence determination and analysis, genetic structure, sequence comparisons and phylogenetic analysis, quantitative real-time PCR expression analysis, recombinant overexpression in Arabidopsis thaliana Col-0 using the Agrobacterium tumefaciens strain GV310 transformation method. Gene PeMPEC driven by the CAMV 35S promoter is transferred into the Crd1 mutant leading to functional complementation of the mutant, the chlorophyll concentration of sense plants is 22-50% higher than that of the Crd1 mutant, and 7-20% higher than that of wild-type Col-0
A0A0K1L5Y4
gene xantha-1, DNA and amino acid sequence determination and analysis
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gene xantha-1, DNA and amino acid sequence determination and analysis, expression of wild-type and mutants in transgenic barley plants
gene ygl8 encodes a catalytic subunit of MgPME cyclase, DNA and amino acid sequence determination and analysis, map-based cloning, sequence comparisons and phylogenetic analysis. Transient expression in Nicotiana benthamiana. The recombinant construct pC1305-YGL8 is introduced into the ygl8 rice mutant by Agrobacterium tumefaciens EHA105-mediated transformation. Quantitative real-time PCR expression analysis
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genes chlAI, chlAII, slr0905, sll1242, or slr0309, expression of wild-type and mutants enzymes, expression analysis, overview
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PCR-amplification of cDNA from isolated RNA, PCR-products of enzyme-GFP fusion constructs are cloned into vector pPENSOTG and introduced into Arabidopsis protoplasts by polyethylene glycol-mediated transformation, complementation constructs are produced by joining PCR fragments of the enzyme promoter with the enzyme-GFP cDNA, cloned into vector pBIB-HYG, introduced into Agrobacterium GV3101, transformed into homozygous mutant plants via the floral dipping method
RNA is isolated to synthesize cDNA and quantitative real-time PCR is carried out for anaerobic and semiaerobic growth conditions
YL-1 subunit of MPEC by map-based cloning, quantitative real-time PCR expression analysis, phylogenetic analysis
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
endogenous 24 h rhythm and regulation by phytochrome in the dark
exposure to far-red radiation at the end of day or red radiation in the middle of night reduce PNZIP mRNA (phytochrome regulation in the dark)
radiant energy and low temperature
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strong irradiance
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temperature has a temporally sensitive and complex effect on PeMPEC transcription
A0A0K1L5Y4
the aerobic magnesium-protoporphyrin IX monomethyl ester (oxidative) cyclase is expressed under semiaerobic and anaerobic conditions, the levels are similar under semiaerobic and anaerobic conditions
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
N182S
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the ygl8 mutation causes a conserved amino acid substitution, which is related to the alterations of chlorophyll precursor content
A96T
site-directed mutagenesis, the point mutation in OsCRD1 does not change its location, but leads to deficiency in chlorophyll biosynthesis and chloroplast development and decreases photosynthetic capacity in rice, phenotype
G286A
naturally occurring mutation, the mutation in enzyme MPEC causes the phenotype of the rice pale-green leaf mutant m167, phenotype
additional information
Renatured/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
reconstitution of the enzyme system from a high-speed supernatant and a membrane pellet
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
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the Rhodobacter capsulatus kanamycin-resistant transposon bchE mutant strain DB575 is used for production of Mg-protoporphyrin IX monomethylester, method development, overview
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