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Information on EC 4.2.1.78 - (S)-norcoclaurine synthase
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4.2.1.78 (S)-norcoclaurine synthaseIUBMB Comments
The reaction makes a six-membered ring by forming a bond between C-6 of the 3,4-dihydroxyphenyl group of the dopamine and C-1 of the aldehyde in the imine formed between the substrates. The product is the precursor of the benzylisoquinoline alkaloids in plants. The enzyme, formerly known as (S)-norlaudanosoline synthase, will also catalyse the reaction of 4-(2-aminoethyl)benzene-1,2-diol + (3,4-dihydroxyphenyl)acetaldehyde to form (S)-norlaudanosoline, but this alkaloid has not been found to occur in plants.
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- 4.2.1.78
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nanocrystals
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nanoclusters
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photoluminescence
- nanoparticles
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excitons
-
as-prepared
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doping
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monodisperse
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electrocatalytic
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tunability
- synthesis
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vacancy
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radiative
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as-synthesized
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photocurrent
The enzyme appears in viruses and cellular organisms
Synonyms
ncs, pbncs, norcoclaurine synthase, csncs, pr10a, (s)-norcoclaurine synthase, cjncs1, cjpr10a, tfncs, (s)-norlaudanosoline synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(S)-norcoclaurine synthase
(S)-Norlaudanosoline synthase
CjPR10A
NCS
NCS1
norcoclaurine synthase
Synthase, (S)-norlaudanosoline
-
-
-
-
additional information
(S)-Norlaudanosoline synthase
-
-
-
-
additional information
-
norcoclaurine synthase is a member of the pathogenesis-related 10/Bet v1 protein family
additional information
-
norcoclaurine synthase is a member of the pathogenesis-related 10/Bet v1 protein family
additional information
-
norcoclaurine synthase is a member of the pathogenesis-related 10/Bet v1 protein family
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-hydroxyphenylacetaldehyde + dopamine = (S)-norcoclaurine + H2O
-
-
-
-
4-hydroxyphenylacetaldehyde + dopamine = (S)-norcoclaurine + H2O
the reaction makes a 6-membered ring by forming a bond between C-6 of the 3,4-dihydroxyphenyl group of the dopamine and C-1 of the aldehyde in the imine formed between the substrates
-
-
-
4-hydroxyphenylacetaldehyde + dopamine = (S)-norcoclaurine + H2O
the reaction makes a six-membered ring by forming a bond between C-6 of the 3,4-dihydroxyphenyl group of the dopamine and C-1 of the aldehyde in the imine formed between the substrates, the product is the precursor of the benzylisoquinoline alkaloids in plants, the enzyme, formerly known as (S)-norleudanosoline synthase, will also catalyse the reaction of 4-(2-aminoethyl)benzene-1,2-diol + (di-3,4-hydroxyphenyl)acetaldehyde to form (S)-norlaudanosoline, but this alkaloid has not been found to occur in plants, cooperativity between substrate binding sites
-
4-hydroxyphenylacetaldehyde + dopamine = (S)-norcoclaurine + H2O
the reaction makes a six-membered ring by forming a bond between C-6 of the 3,4-dihydroxyphenyl group of the dopamine and C-1 of the aldehyde in the imine formed between the substrates, the product is the precursor of the benzylisoquinoline alkaloids in plants, the enzyme, formerly known as (S)-norleudanosoline synthase, will also catalyse the reaction of 4-(2-aminoethyl)benzene-1,2-diol + (di-3,4-hydroxyphenyl)acetaldehyde to form (S)-norlaudanosoline, but this alkaloid has not been found to occur in plants, cooperativity between substrate binding sites
-
4-hydroxyphenylacetaldehyde + dopamine = (S)-norcoclaurine + H2O
the reaction makes a six-membered ring by forming a bond between C-6 of the 3,4-dihydroxyphenyl group of the dopamine and C-1 of the aldehyde in the imine formed between the substrates, the product is the precursor of the benzylisoquinoline alkaloids in plants, the enzyme, formerly known as (S)-norleudanosoline synthase, will also catalyse the reaction of 4-(2-aminoethyl)benzene-1,2-diol + (di-3,4-hydroxyphenyl)acetaldehyde to form (S)-norlaudanosoline, but this alkaloid has not been found to occur in plants, cooperativity between substrate binding sites
Thalictrum flavum ssp. glaucum
-
4-hydroxyphenylacetaldehyde + dopamine = (S)-norcoclaurine + H2O
the reaction makes a six-membered ring by forming a bond between C-6 of the 3,4-dihydroxyphenyl group of the dopamine and C-1 of the aldehyde in the imine formed between the substrates, the product is the precursor of the benzylisoquinoline alkaloids in plants, the enzyme, formerly known as (S)-norleudanosoline synthase, will also catalyse the reaction of 4-(2-aminoethyl)benzene-1,2-diol + (di-3,4-hydroxyphenyl)acetaldehyde to form (S)-norlaudanosoline, but this alkaloid has not been found to occur in plants, iso-ordered bi-uni mechanism with 4-hydroxyphenylacetaldehyde binding before dopamine
Thalictrum flavum ssp. glaucum
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
condensation
condensation
-
-
amine + aldehyde
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
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SYSTEMATIC NAME
IUBMB Comments
4-hydroxyphenylacetaldehyde hydro-lyase [adding dopamine; (S)-norcoclaurine-forming]
The reaction makes a six-membered ring by forming a bond between C-6 of the 3,4-dihydroxyphenyl group of the dopamine and C-1 of the aldehyde in the imine formed between the substrates. The product is the precursor of the benzylisoquinoline alkaloids in plants. The enzyme, formerly known as (S)-norlaudanosoline synthase, will also catalyse the reaction of 4-(2-aminoethyl)benzene-1,2-diol + (3,4-dihydroxyphenyl)acetaldehyde to form (S)-norlaudanosoline, but this alkaloid has not been found to occur in plants.
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CAS REGISTRY NUMBER
COMMENTARY
389139-02-0
-
79122-01-3
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(2-fluorophenyl)acetaldehyde + dopamine
(1S)-1-[2-(2-fluorophenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
65% conversion after 3 h
-
-
?
(2-methylphenyl)acetaldehyde + dopamine
(1S)-1-[2-(2-methylphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
66% conversion after 3 h
-
-
?
(3,4-dimethoxyphenyl)acetaldehyde + dopamine
(1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
69% conversion after 3 h
-
-
?
(3-fluorophenyl)acetaldehyde + dopamine
(1S)-1-[2-(3-fluorophenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
66% conversion after 3 h
-
-
?
(3-methylphenyl)acetaldehyde + dopamine
(1S)-1-[2-(3-methylphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
58% conversion after 3 h
-
-
?
(4-fluorophenyl)acetaldehyde + dopamine
(1S)-1-[2-(4-fluorophenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
71% conversion after 3 h
-
-
?
(4-methoxyphenyl)acetaldehyde + dopamine
(1S)-1-[2-(4-methoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
69% conversion after 3 h
-
-
?
(4-methylphenyl)acetaldehyde + dopamine
(1S)-1-[2-(4-fluorophenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
57% conversion after 3 h
-
-
?
(5,5-dimethyl-1,3-dioxan-2-yl)acetaldehyde + dopamine
(1S)-1-[2-(5,5-dimethyl-1,3-dioxan-2-yl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
42% conversion after 3 h
-
-
?
1-butylaldehyde + dopamine
6,7-dihydroxy-1-propyl-1,2,3,4-tetrahydroisoquinoline
molar yield and enantiomeric excess of 6,7-dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline are 99.6 and 98.0 %, respectively
-
-
?
3,3-dimethylbutanal + dopamine
(1S)-1-(3,3-dimethylbutyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
52% conversion after 3 h
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + (3,4-dihydroxyphenyl)acetaldehyde
?
-
-
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
4-hydroxyphenylacetone + dopamine
1-(4-hydroxybenzyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
-
-
-
?
cyclohexylacetaldehyde + dopamine
(1S)-1-(2-cyclohexylethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
71% conversion after 3 h
-
-
?
hydrocinnamaldehyde + dopamine
6,7-dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline
molar yield and enantiomeric excess of 6,7-dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline are 86.0 and 95.3%, respectively
-
-
?
naphthalen-1-ylacetaldehyde + dopamine
(1S)-1-[2-(naphthalen-1-yl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
61% conversion after 3 h
-
-
?
phenylacetaldehyde + dopamine
(1S)-1-(2-phenylethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
51% conversion after 3 h
-
-
?
thiophen-3-ylacetaldehyde + dopamine
(1S)-1-[2-(thiophen-3-yl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
68% conversion after 3 h
-
-
?
[4-(trifluoromethoxy)phenyl]acetaldehyde + dopamine
(1S)-1-[2-[4-(trifluoromethoxy)phenyl]ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
65% conversion after 3 h
-
-
?
additional information
?
-
-
isozyme NCS1 of Coptis japonica does not catalyze the formation of (S)-norcoclaurine from dopamine and 4-hydroxyphenylacetaldehyde
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
Berberis regeliana
-
-
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
-
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
Eschscholtzia tenuifolia
-
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
Eschscholtzia tenuifolia
-
i.e. dopamine + 3,4-dihydroxyphenylacetaldehyde, , 3,4-dihydroxyphenylacetaldehyde can be substituted by 4-hydroxyphenylacetaldehyde but not by 3,4-dihydroxyphenylpyruvate, 4-hydroxyphenylpyruvate or phenylpyruvate
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
Eschscholzia pulchella
-
-
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
-
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
Glaucium rubrum
-
-
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
-
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
-
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
-
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
Thalictrum flavum ssp. glaucum
-
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
-
-
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
-
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
CjNCS1
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
CjPR10A
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Eschscholtzia tenuifolia
-
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Eschscholtzia tenuifolia
-
i.e. dopamine + 4-hydroxyphenylacetaldehyde, , 4-hydroxyphenylacetaldehyde can be substituted by 3,4-dihydroxyphenylacetaldehyde but not by 3,4-dihydroxyphenylpyruvate, 4-hydroxyphenylpyruvate or phenylpyruvate
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
4-(2-aminoethyl)benzene-1,2-diol is dopmaine
-
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
-
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
4-(2-aminoethyl)benzene-1,2-diol is dopmaine
-
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
-
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
-
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
-
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
the enzyme is involved in the plants secondary metabolism and is required for the production of bioactive secondary metabolites like morphine
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Thalictrum flavum ssp. glaucum
-
4-(2-aminoethyl)benzene-1,2-diol is dopmaine
-
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Thalictrum flavum ssp. glaucum
-
4-(2-aminoethyl)benzene-1,2-diol is dopmaine, cooperativity between the dopamine binding sites on each subunit
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Thalictrum flavum ssp. glaucum
-
first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Thalictrum flavum ssp. glaucum
-
first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
-
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Berberis regeliana
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Eschscholtzia tenuifolia
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Eschscholzia pulchella
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Glaucium rubrum
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
4-(2-aminoethyl)benzene-1,2-diol, i.e. dopamine
-
-
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
4-(2-aminoethyl)benzene-1,2-diol, i.e. dopamine
-
-
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
4-(2-aminoethyl)benzene-1,2-diol, i.e. dopamine
-
-
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
stereospecific formation of the (S)-norcolaurine enantiomer by the recombinant enzyme, overview
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
-
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
-
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
the enzyme is involved in the biosynthesis of benzylisoquinoline
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
the enzyme catalyzes the stereoselective Pictet-Spengler reaction between dopamine and 4-hydroxyphenylacetaldehyde as a step of benzylisoquinoline alkaloid synthesis in plants
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Corydalis chinensis
-
the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
the enzyme is involved in the biosynthesis of benzylisoquinoline
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
the enzyme is involved in the biosynthesis of benzylisoquinoline
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
60% conversion after 3 h
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
-
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
-
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
-
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
-
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
the enzyme is involved in the plants secondary metabolism and is required for the production of bioactive secondary metabolites like morphine
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Thalictrum flavum ssp. glaucum
-
first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Thalictrum flavum ssp. glaucum
-
first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
-
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Berberis regeliana
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Eschscholtzia tenuifolia
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Eschscholzia pulchella
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Glaucium rubrum
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
initial reaction in isoquinoline biosynthesis
-
-
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
4-(2-aminoethyl)benzene-1,2-diol, i.e. dopamine
-
-
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
4-(2-aminoethyl)benzene-1,2-diol, i.e. dopamine
-
-
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
4-(2-aminoethyl)benzene-1,2-diol, i.e. dopamine
-
-
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
stereospecific formation of the (S)-norcolaurine enantiomer by the recombinant enzyme, overview
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
-
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
-
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
the enzyme is involved in the biosynthesis of benzylisoquinoline
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
the enzyme catalyzes the stereoselective Pictet-Spengler reaction between dopamine and 4-hydroxyphenylacetaldehyde as a step of benzylisoquinoline alkaloid synthesis in plants
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Corydalis chinensis
-
the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
the enzyme is involved in the biosynthesis of benzylisoquinoline
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
the enzyme is involved in the biosynthesis of benzylisoquinoline
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
60% conversion after 3 h
-
-
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
Thalictrum flavum ssp. glaucum
-
the enzyme is not affected by divalent cations
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
-
no inhibition by several benzylisochinoline alkaloids, enzyme is not affected by Mg2+ and Ca2+
-
additional information
-
immunoprecipitation of NCS from total protein extracts of Thalictrum flavum cells results in a nearly complete attenuation of NCS activity
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
fungal elicitor of Bortrytis sp.
-
isolated elicitor induces the enzyme activity in cell suspension culture 20fold
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.33
4-hydroxyphenylacetaldehyde
wild-type, 37°C, 0.1 M phosphate buffer pH 7.5
0.335
4-hydroxyphenylacetaldehyde
Thalictrum flavum ssp. glaucum
-
pH 7.5, 37°C, hyperbolic saturation kinetics
0.36
4-hydroxyphenylacetaldehyde
mutant Y108F, 37°C, 0.1 M phosphate buffer pH 7.5
0.42
4-hydroxyphenylacetaldehyde
Thalictrum flavum ssp. glaucum
-
pH 7.0, 37°C, hyperbolic saturation kinetics
0.505
4-hydroxyphenylacetaldehyde
mutant E110A, 37°C, 0.1 M phosphate buffer pH 7.5
0.66
4-hydroxyphenylacetaldehyde
-
pH 7.0, 37°C, hyperbolic saturation kinetics
1
4-hydroxyphenylacetaldehyde
-
pH 7.0, 37°C, hyperbolic saturation kinetics
additional information
additional information
-
kinetics, sigmoidal saturation kinetics for dopamine, Hill coeffcient 1.84, cooperativity between the dopamine binding sites on each subunit
-
additional information
additional information
Thalictrum flavum ssp. glaucum
-
kinetics, sigmoidal saturation kinetics for dopamine, Hill coeffcient 2.16, cooperativity between the dopamine binding sites on each subunit
-
additional information
additional information
-
kinetics, sigmoidal saturation kinetics for dopamine, Hill coeffcient 2.19, cooperativity between the dopamine binding sites on each subunit
-
additional information
additional information
Thalictrum flavum ssp. glaucum
-
sigmoidal saturation kinetics for dopamine, cooperativity between the dopamine binding sites on each subunit
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
7
(3,4-dihydroxyphenyl)acetaldehyde
-
cosubstrate: 4-(2-aminoethyl)benzene-1,2-diol
6
5-(2-aminoethyl)-2-methoxyphenol
-
cosubstrate: 4-(2-aminoethyl)benzene-1,2-diol
6.4
4-(2-Aminoethyl)benzene-1,2-diol
-
cosubstrate: 4-(2-aminoethyl)benzene-1,2-diol
7
4-(2-Aminoethyl)benzene-1,2-diol
-
cosubstrate: (3,4-dihydroxyphenyl)acetaldehyde
0.8
4-hydroxyphenylacetaldehyde
mutant E110A, 37°C, 0.1 M phosphate buffer pH 7.5
1.7
4-hydroxyphenylacetaldehyde
mutant Y108F, 37°C, 0.1 M phosphate buffer pH 7.5
4.5
4-hydroxyphenylacetaldehyde
wild-type, 37°C, 0.1 M phosphate buffer pH 7.5
6
4-hydroxyphenylacetaldehyde
-
cosubstrate: 5-(2-aminoethyl)-2-methoxyphenol
6.4
4-hydroxyphenylacetaldehyde
-
cosubstrate: 4-(2-aminoethyl)benzene-1,2-diol
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5 - 7
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.2 - 9
-
50% of maximal activity at pH 6.2, 68% of maximal activity at pH 9.0
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
45 - 55
50
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TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37 - 57
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Thalictrum flavum ssp. glaucum
Thalictrum flavum ssp. glaucum
i.e. meadow rue, 4 isoelectrically different isozymes
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
NCS2 shows cell type-specific occurrence in phloem sieve elements, colocalization with all other known benzylisoquinoline alkaloid biosynthetic enzymes
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
NCS2 has an N-terminal signal peptide and sorts to the vacuole
brenda
additional information
-
immunolocalization study of NCS, overview
-
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
evolution
-
evolutionary origin of the NCSI gene subfamily encoding norcoclaurine synthase
metabolism
physiological function
-
key steps in the biotransformation consist of the oxidative decarboxylation of tyrosine by stoichiometric amounts of sodium hypochlorite in order to generate 4-hydroxyphenylacetadehyde, followed by the addition of enzyme and dopamine substrate in the presence of ascorbate, a necessary ingredient in order to avoid oxidation of the catechol moiety
additional information
metabolism
-
norcoclaurine synthase, NCS, catalyzes the first committed step in the biosynthesis of benzylisoquinoline alkaloids, exclusive role of PR10/Bet v1-type NCS enzymes, overview
metabolism
-
norcoclaurine synthase, NCS, catalyzes the first committed step in the biosynthesis of benzylisoquinoline alkaloids, exclusive role of PR10/Bet v1-type NCS enzymes, overview
metabolism
-
norcoclaurine synthase, NCS, catalyzes the first committed step in the biosynthesis of benzylisoquinoline alkaloids, exclusive role of PR10/Bet v1-type NCS enzymes, overview
metabolism
the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
metabolism
the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
metabolism
-
the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
metabolism
Corydalis chinensis
-
the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
metabolism
the enzyme catalyzes the stereoselective Pictet-Spengler reaction between dopamine and 4-hydroxyphenylacetaldehyde as a step of benzylisoquinoline alkaloid synthesis in plants
metabolism
the enzyme is a Pictet-Spenglerase that catalyzes a step in plant benzylisoquinoline alkaloid metabolism, a compound family that includes bioactive natural products such as morphine
metabolism
-
the enzyme is involved in biosynthesis of benzylisoquinoline alkaloids
metabolism
the enzyme is involved in the biosynthesis of benzylisoquinoline
metabolism
the enzyme is involved in the biosynthesis of benzylisoquinoline
metabolism
the enzyme is involved in the biosynthetic of benzylisoquinoline
additional information
-
amino acid sequence comparisons of NCSs from different species, phylogenetic tree, overview
additional information
-
amino acid sequence comparisons of NCSs from different species, phylogenetic tree, overview
additional information
-
amino acid sequence comparisons of NCSs from different species, phylogenetic tree, overview
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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). NCS1_COPJA
352
0
39964
Swiss-Prot
other Location (Reliability: 3)
NCS1_PAPSO
231
1
26015
Swiss-Prot
other Location (Reliability: 5)
NCS2_COPJA
196
1
22160
Swiss-Prot
Secretory Pathway (Reliability: 2)
NCS2_PAPSO
231
1
26001
Swiss-Prot
other Location (Reliability: 4)
NCS_THLFG
210
0
23341
Swiss-Prot
Secretory Pathway (Reliability: 1)
A0A097H1C2_SINHE
194
0
21738
TrEMBL
Secretory Pathway (Reliability: 4)
A0A191T7P5_NELNU
155
0
17135
TrEMBL
other Location (Reliability: 3)
A0A2P6SPV2_ROSCH
158
0
17586
TrEMBL
other Location (Reliability: 4)
A0A191T7P4_NELNU
161
0
17951
TrEMBL
other Location (Reliability: 3)
A0A191T7N6_NELNU
162
0
18459
TrEMBL
other Location (Reliability: 3)
A0A2P6P9S2_ROSCH
361
0
40783
TrEMBL
other Location (Reliability: 2)
A0A2P6SPZ3_ROSCH
103
0
11396
TrEMBL
other Location (Reliability: 5)
D2SMN3_ARGME
220
1
24398
TrEMBL
other Location (Reliability: 4)
A0A2P6SPZ1_ROSCH
95
0
10604
TrEMBL
other Location (Reliability: 5)
A0A2G9GHQ6_9LAMI
146
0
16326
TrEMBL
other Location (Reliability: 2)
A0A072ULU0_MEDTR
161
0
17928
TrEMBL
other Location (Reliability: 3)
A0A396H0B9_MEDTR
360
0
41396
TrEMBL
other Location (Reliability: 3)
G7KU18_MEDTR
323
0
37090
TrEMBL
other Location (Reliability: 3)
A0A0B4VGL7_PODPE
111
0
12309
TrEMBL
other Location (Reliability: 3)
A0A2P6R9Z5_ROSCH
135
0
15340
TrEMBL
Chloroplast (Reliability: 5)
A0A2P6R9X7_ROSCH
535
0
60330
TrEMBL
other Location (Reliability: 2)
D2SMN1_ARGME
275
1
30685
TrEMBL
other Location (Reliability: 4)
A0A396GYH0_MEDTR
95
0
10961
TrEMBL
other Location (Reliability: 2)
A0A072UNP4_MEDTR
162
0
18093
TrEMBL
other Location (Reliability: 2)
A0A2P6PKZ0_ROSCH
348
0
39102
TrEMBL
other Location (Reliability: 2)
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
21180
-
mass spectrometry of recombinant Delta29NCS (coding for amino acids 30210 of NCS)
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
tetramer
composed of two asymmetric units, each containing a single dimer (A1-B1 or A2-B2)
additional information
-
size-exclusion chromatography (SEC) and NMR relaxation measurements, concentration-dependent oligomerization of delta 29NCS with an equilibrium of monomeric and oligomeric protein over a broad concentration range, at low protein concentrations in the range of 10 microM the enzyme is predominantly monomeric, no indication that substrate binding induces dimerization of delta 29NCS
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
at 294 K by the hanging-drop vapour-diffusion method using ammonium sulfate and sodium chloride as precipitant agents and diffract to better than 3.0 A resolution using a synchrotron-radiation source. The crystals belong to the trigonal space group P3121, with unit-cell parameters a = b = 86.31, c = 118.36 A. A selenomethionine derivate is crystallized in the same space group, 2.7 A resolution
combining experimental NMR spectroscopic data with homology modelling using the homologous major birch pollen allergen Bet v 1 (PDB code 1BV1) as template structure a reliable model structure of delta 29NCS is built
-
high-resolution X-ray crystallography. The structure supports two features of the dopamine-first mechanism: the binding of dopamine catechol to Lys-122 and the position of the carbonyl substrate binding site at the active site entrance. The catalytically vital residue Glu-110 occupies a ligand-bound conformation that may be catalytically significant
SeMet derivate of NCS unligated (2VNE) and substrate-bound (2VQ5), by the hanging-drop vapour-diffusion method using ammonium sulfate and sodium chloride as precipitant agents, SeMet NCS: 2.7A resolution, 298K, ammoniumsulfate 1.4-1.8 M, NaCl 0.2 M, acetate buffer pH 4.0-4.5, trigonal space group P3121 with unit cell dimensions a = b = 86.31 A, c = 118.36 A, alpha = beta = 90°, gamma = 120°
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
A79F
improved turnover of ketones, increase in side-chain steric interactions
A79I
improved turnover of ketones, increase in side-chain steric interactions
Y108A
site-directed mutagenesis abolishes the stereoselective synthesis of (S)-norcoclaurine
additional information
-
virus-induced gene silencing of NCS in opium poppy profoundly reduces alkaloid levels compared to controls, a mixed culture of Agrobacterium tumefaciens harboring either pTRV2-PsNCS or pTRV1 is infiltrated into opium poppy seedlings tow weeks after germination. Levels of the five major alkaloids in opium poppy latex, i.e. morphine, codeine, thebaine, noscapine, and papaveine, are reduced by 75-82% in plants infiltrated with Agrobacterium tumefaciens harboring pTRV2-PsNCS
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80C, purified enzyme, 7 days, no loss of activity
4C, purified enzyme, 7 days, 75% loss of activity
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
HisTrap Fast Flow column equilibrated with a 50 mM Tris HCl buffer at pH 7.5. A linear gradient of imidazole concentration from 0 to 0.5 M (buffered at pH 7.5) is applied
recombinant C-terminally His-tagged NCS from Eschericha coli strain BL21(DE3) by nickel affinity chromatography
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
expression in Escherichia coli and in Saccharomyces cereviseae
expression in Escherichia coli BL21 (DE3)
expression in Escherichia coli BL21 (DE3). Under certain conditions lyophilized whole Escherichia coli cells containing the overexpressed enzyme turn out to a suitable catalysts
N-terminally truncated enzyme (CjNCS-DELTA29, with a deletion of the first 29 amino acid residues) is expressed in Escherichia coli. The cell-free extract of Escherichia coli expressing CjNCS-DELTA29 exhibits 40fold higher activity than that expressing intact enzyme
NCS2-green fluorescent protein fusion introduced by microprojectile bombardment into opium poppy cells initially localizes to the endoplasmic reticulum but subsequently sorts to the vacuole
-
recombinant expression of C-terminally His-tagged NCS in Eschericha coli strain BL21(DE3)
-
the NCS protein truncated at the first 19 amino acids with an N-terminal MTGS sequence and a His tag at the C-terminus and its SeMet-substituted variant are subcloned into the NdeI and XhoI restriction sites of the vector pET22b. Transformation of chemically competent Escherichia coli strain BL21DE is performed and transformed cells are plated onto LB-ampicillin plates
the NCS protein truncated at the first 19 amino acids, with a N-terminal MTGS sequence and a His tag at the C terminus is subcloned into the NdeI and XhoI restriction site of the vector pET22-b. Transformation of chemically competent Escherichia coli strain BL21DE3
unlabelled and 15N-labelled delta 29NCS is expressed using the expression system Escherichia coli Rosetta(DE3)/pET29b-delta 29NCS
-
expression in Escherichia coli and in Saccharomyces cereviseae
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
elicitor-induced cell cultures show increasing expression of NCS after 2 to 100 hours
-
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
-
development of an efficient, stereoselective, green synthesis of (S)-norcoclaurine, i.e. higenamine, using the recombinant (S)-norcoclaurine synthase enzyme, starting from the cheap tyrosine and dopamine substrates in a one-pot, two step process, overview. The optimized process affords enantiomerically pure (S)-norcoclaurine (93%) in a yield higher than 80% and allows good recovery of the enzyme for recycling, by a green Pictet-Spengler synthesis
synthesis
the enzyme can catalyse the Pictet-Spengler reaction between dopamine and unactivated ketones, thus facilitating the facile biocatalytic generation of 1,1'-disubstituted tetrahydroisoquinolines. Variants of the enzyme showing improved conversions are identified and used to synthesize novel chiral 1,10-disubstituted and spiro-tetrahydroisoquinolines
synthesis
the enzyme can serve as a tool to synthesize unnatural, optically active tetrahydroisoquinolines. The enzyme is a promising catalyst that functions to stereoselectively produce various 1-substituted-1,2,3,4-tetrahydroisoquinolines
synthesis
the enzyme has also shown great potential as a biocatalyst for the formation of chiral isoquinolines
synthesis
the enzyme is a highly suitable catalyst for the Pictet-Spengler reaction
synthesis
the enzyme is a highly suitable catalyst for the Pictet-Spengler reaction
synthesis
the enzyme is a highly suitable catalyst for the Pictet-Spengler reaction. The enzyme is successfully immobilized on various carriers whereby EziG3 proves to be the best suited for biotransformations
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Rueffer, M.; El-Shagi, H.; Nagakura, N.; Zenk, M.H.
(S)-Norlaudanosoline synthase: the first enzyme in the benzylisoquinoline biosynthetic pathway
FEBS Lett.
129
5-9
1981
Berberis regeliana, Capnoides sempervirens, Lamprocapnos spectabilis, Eschscholzia pulchella, Eschscholtzia tenuifolia, Fumaria officinalis, Glaucium rubrum, Meconopsis cambrica, Papaver somniferum, Ranunculus flammula, Thalictrum minus, Thalictrum tuberosum
-
brenda
Schumacher, H.M.; Rueffer, M.; Nagakura, N.; Zenk, M.H.
Partial purification and properties of (S)-norlaudanosoline synthase from Eschscholtzia tenuifolia cell cultures
J. Med. Plant Res.
48
212-220
1983
Eschscholtzia tenuifolia
brenda
Samanani, N.; Facchini, P.J.
Purification and characterization of norcoclaurine synthase. The first committed enzyme in benzylisoquinoline alkaloid biosynthesis in plants
J. Biol. Chem.
277
33878-33883
2002
Thalictrum flavum ssp. glaucum
brenda
Samanani, N.; Facchini, P.J.
Isolation and partial characterization of norcoclaurine synthase, the first committed step in benzylisoquinoline alkaloid biosynthesis, from opium poppy
Planta
213
898-906
2001
Eschscholzia californica, no activity in Catharanthus roseus, no activity in Nicotiana tabacum, Papaver somniferum, Thalictrum flavum ssp. glaucum
brenda
Luk, L.Y.; Bunn, S.; Liscombe, D.K.; Facchini, P.J.; Tanner, M.E.
Mechanistic studies on norcoclaurine synthase of benzylisoquinoline alkaloid biosynthesis: an enzymatic Pictet-Spengler reaction
Biochemistry
46
10153-10161
2007
Thalictrum flavum
brenda
Minami, H.; Dubouzet, E.; Iwasa, K.; Sato, F.
Functional analysis of norcoclaurine synthase in Coptis japonica
J. Biol. Chem.
282
6274-6282
2007
Coptis japonica
brenda
Berkner, H.; Engelhorn, J.; Liscombe, D.K.; Schweimer, K.; Woehrl, B.M.; Facchini, P.J.; Roesch, P.; Matecko, I.
High-yield expression and purification of isotopically labeled norcoclaurine synthase, a Bet v 1-homologous enzyme, from Thalictrum flavum for NMR studies
Protein Expr. Purif.
56
197-204
2007
Thalictrum flavum
brenda
Pasquo, A.; Bonamore, A.; Franceschini, S.; Macone, A.; Boffi, A.; Ilari, A.
Cloning, expression, crystallization and preliminary X-ray data analysis of norcoclaurine synthase from Thalictrum flavum
Acta Crystallogr. Sect. F
64
281-283
2008
Thalictrum flavum (Q67A25), Thalictrum flavum
brenda
Berkner, H.; Schweimer, K.; Matecko, I.; Roesch, P.
Conformation, catalytic site, and enzymatic mechanism of the PR10 allergen-related enzyme norcoclaurine synthase
Biochem. J.
413
281-290
2008
Thalictrum flavum
brenda
Ilari, A.; Franceschini, S.; Bonamore, A.; Arenghi, F.; Botta, B.; Macone, A.; Pasquo, A.; Bellucci, L.; Boffi, A.
Structural basis of enzymatic (S)-norcoclaurine biosynthesis
J. Biol. Chem.
284
897-904
2009
Thalictrum flavum (Q67A25), Thalictrum flavum
brenda
Michalska, K.; Fernandes, H.; Sikorski, M.; Jaskolski, M.
Crystal structure of Hyp-1, a St. Johns wort protein implicated in the biosynthesis of hypericin
J. Struct. Biol.
169
161-171
2010
Hypericum perforatum
brenda
Bonamore, A.; Rovardi, I.; Gasparrini, F.; Baiocco, P.; Barba, M.; Molinaro, C.; Botta, B.; Boffi, A.; MacOne, A.
An enzymatic, stereoselective synthesis of (S)-norcoclaurine
Green Chem.
12
1623-1627
2010
Thalictrum flavum
-
brenda
Lee, E.J.; Facchini, P.
Norcoclaurine synthase is a member of the pathogenesis-related 10/Bet v1 protein family
Plant Cell
22
3489-3503
2010
Coptis japonica, Papaver somniferum, Thalictrum flavum
brenda
De la Cruz-Chacon, I.; Gonalez-Esquinca, A.
Activities of enzymes catalyzing benzylisoquinoline alkaloid biosynthesis in Annona diversifolia saff. during early development
Russ. J. Plant Physiol.
60
791-799
2013
Annona macroprophyllata
-
brenda
Zhang, X.; Ma, L.; Tian, Y.; Zhang, G.; Luo, Y.
Molecular cloning and heterologous expression of putative (S)-norcoclaurine synthases from Arabidopsis thaliana
Chin. J. Appl. Environ. Biol.
19
61-68
2013
Arabidopsis thaliana
-
brenda
Ruff, B.M.; Braese, S.; O'Connor, S.E.
Biocatalytic production of tetrahydroisoquinolines
Tetrahedron Lett.
53
1071-1074
2012
Thalictrum flavum
brenda
Lichman, B.R.; Sula, A.; Pesnot, T.; Hailes, H.C.; Ward, J.M.; Keep, N.H.
Structural evidence for the dopamine-first mechanism of norcoclaurine synthase
Biochemistry
56
5274-5277
2017
Thalictrum flavum (Q67A25), Thalictrum flavum
brenda
Nishihachijo, M.; Hirai, Y.; Kawano, S.; Nishiyama, A.; Minami, H.; Katayama, T.; Yasohara, Y.; Sato, F.; Kumagai, H.
Asymmetric synthesis of tetrahydroisoquinolines by enzymatic Pictet-Spengler reaction
Biosci. Biotechnol. Biochem.
78
701-707
2014
Coptis japonica (A2A1A1), Coptis japonica
brenda
Lechner, H.; Soriano, P.; Poschner, R.; Hailes, H.C.; Ward, J.M.; Kroutil, W.
Library of norcoclaurine synthases and their immobilization for biocatalytic transformations
Biotechnol. J.
13
e1700542
2018
Papaver bracteatum (C3SBT7), Papaver bracteatum, Argemone mexicana (D2SMN1), Argemone mexicana (D2SMN3), Argemone mexicana, Corydalis saxicola (F5C449), Corydalis saxicola
brenda
Lichman, B.R.; Zhao, J.; Hailes, H.C.; Ward, J.M.
Enzyme catalysed Pictet-Spengler formation of chiral 1,1-disubstituted- and spiro-tetrahydroisoquinolines
Nat. Commun.
8
14883
2017
Thalictrum flavum (Q67A25), Thalictrum flavum
brenda
Vimolmangkang, S.; Deng, X.; Owiti, A.; Meelaph, T.; Ogutu, C.; Han, Y.
Evolutionary origin of the NCSI gene subfamily encoding norcoclaurine synthase is associated with the biosynthesis of benzylisoquinoline alkaloids in plants
Sci. Rep.
6
26323
2016
Nelumbo nucifera
brenda
Li, J.; Lee, E.J.; Chang, L.; Facchini, P.J.
Genes encoding norcoclaurine synthase occur as tandem fusions in the Papaveraceae
Sci. Rep.
6
39256
2016
Nandina domestica, Corydalis chinensis, Papaver somniferum (Q4QTJ1), Papaver somniferum (Q4QTJ2), Papaver somniferum, Thalictrum flavum (Q67A25)
brenda
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