Information on EC 1.14.14.102 - N-methylcoclaurine 3'-monooxygenase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.14.102
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RECOMMENDED NAME
GeneOntology No.
N-methylcoclaurine 3'-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2 = (S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydroxylation
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
(S)-reticuline biosynthesis I
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Isoquinoline alkaloid biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
(S)-N-methylcoclaurine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
A heme-thiolate protein (P-450) involved in benzylisoquinoline alkaloid synthesis in higher plants.
CAS REGISTRY NUMBER
COMMENTARY hide
202420-37-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
isozyme 2; 2 isozymes, 2 cultivars
UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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enzyme silencing is associated with a 22% reduction in total alkaloid accumulation, with a notable decrease in the levels of thebaine and codeine compared with controls. In contrast, absolute levels of morphine and papaverine are not affected
metabolism
physiological function
the expression of isozyme 1 is low in the two cultivars, so it may have little effect on alkaloid contents. The expression of CYP80B, NNU08355, has a positive effect on aporphine alkaloids content in lotus, but exhibits phenotypic lag, which might be because of NMCH which acts early in the benzylisoquinoline alkaloid biosynthetic pathway
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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
(S)-N-methylcoclaurine + [reduced NADPH-hemoprotein reductase] + O2
(S)-3'-hydroxy-N-methylcoclaurine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P-450
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cytochrome P450
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NADPH-hemoprotein reductase
A flavoprotein containing both FMN and FAD. This enzyme catalyses the transfer of electrons from NADPH, an obligatory two-electron donor, to microsomal P-450 monooxygenases, EC 1.14.14._
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.015
(S)-N-methylcoclaurine
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
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Tris-HCl buffer
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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localization in the sieve elements adjacent or proximal to laticifers in the root and hypocotyl of opium poppy seedlings
Manually annotated by BRENDA team
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root phloem, the abundance of the enzyme increases rapidly between 1 and 3 days after seed germination
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
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subcellular localization study
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Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55040
calculated from amino acids, 488 amino acids, 1680 bp
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant enzyme
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Saccharomyces cerevisiae and Spodoptera frugiperda
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gene cyp80b3, overexpression in Papaver somniferum plants, expression of anti-sense constructs, construction of transgenic plants using the Agrobacterium tumefaciens, strain AGL1, transfection method, expression of antisense cyp80b3 leads to a reduction of total alkaloid in latex up to 84%, phenotype, overview, enzyme overexpression results in an up to 450% increase in the amount of total alkaloid in latex without changing the ratio of the individual alkaloids, or together with an overall increase in the ratio of morphine
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gene LOC104585940 encoding isozyme 2, DNA and amino acid sequence determination and analysis, phylogenetic analysis, quantitative RT-PCR enzyme expression analysis
heterologous expression
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PDR-amplification
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biotechnology
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the enzyme provides practical means to genetically engineer valuable secondary metabolites in this important medicinal plant
medicine
traditional Chinese medicinal plant containing benzylisoquinoline alkaloids as active agents