Any feedback?
No. of entries
Information on EC 3.5.99.14 - (S)-norcoclaurine synthase
for references in articles please use BRENDA:EC3.5.99.14
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
EC Tree 3 Hydrolases
3.5 Acting on carbon-nitrogen bonds, other than peptide bonds
3.5.99 In other compounds
3.5.99.14 (S)-norcoclaurine synthase
IUBMB 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.
The enzyme appears in viruses and cellular organisms
showSynonyms
(S)-norcoclaurine synthase, (S)-Norlaudanosoline synthase, AmNCS1, AmNCS2, CCHNCS2, CjNCS1, CjPR10A, CsNCS, EC 4.2.1.78, More, more
topPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
(S)-norcoclaurine synthase
(S)-Norlaudanosoline synthase
CjPR10A
NCS
NCS1
NCS2
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(S)-norcoclaurine + H2O = dopamine + 4-hydroxyphenylacetaldehyde
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
-
-
-
(S)-norcoclaurine + H2O = dopamine + 4-hydroxyphenylacetaldehyde
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
-
(S)-norcoclaurine + H2O = dopamine + 4-hydroxyphenylacetaldehyde
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
-
(S)-norcoclaurine + H2O = dopamine + 4-hydroxyphenylacetaldehyde
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
-
(S)-norcoclaurine + H2O = dopamine + 4-hydroxyphenylacetaldehyde
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
-
(S)-norcoclaurine + H2O = dopamine + 4-hydroxyphenylacetaldehyde
-
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
condensation
condensation
-
-
amine + aldehyde
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SYSTEMATIC NAME
IUBMB Comments
(S)-norcoclaurine dopamine hydrolase (4-hydroxyphenylacetaldehyde-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.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CAS REGISTRY NUMBER
COMMENTARY
389139-02-0
-
79122-01-3
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
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
-
Substrates: 65% conversion after 3 h
Products: -
Products: -
?
(2-methylphenyl)acetaldehyde + dopamine
(1S)-1-[2-(2-methylphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
Substrates: 66% conversion after 3 h
Products: -
Products: -
?
(3,4-dimethoxyphenyl)acetaldehyde + dopamine
(1S)-1-[2-(3,4-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
Substrates: 69% conversion after 3 h
Products: -
Products: -
?
(3-fluorophenyl)acetaldehyde + dopamine
(1S)-1-[2-(3-fluorophenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
Substrates: 66% conversion after 3 h
Products: -
Products: -
?
(3-methylphenyl)acetaldehyde + dopamine
(1S)-1-[2-(3-methylphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
Substrates: 58% conversion after 3 h
Products: -
Products: -
?
(4-fluorophenyl)acetaldehyde + dopamine
(1S)-1-[2-(4-fluorophenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
Substrates: 71% conversion after 3 h
Products: -
Products: -
?
(4-methoxyphenyl)acetaldehyde + dopamine
(1S)-1-[2-(4-methoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
Substrates: 69% conversion after 3 h
Products: -
Products: -
?
(4-methylphenyl)acetaldehyde + dopamine
(1S)-1-[2-(4-fluorophenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
Substrates: 57% conversion after 3 h
Products: -
Products: -
?
(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
-
Substrates: 42% conversion after 3 h
Products: -
Products: -
?
1-butylaldehyde + dopamine
6,7-dihydroxy-1-propyl-1,2,3,4-tetrahydroisoquinoline
Substrates: molar yield and enantiomeric excess of 6,7-dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline are 99.6 and 98.0 %, respectively
Products: -
Products: -
?
3,3-dimethylbutanal + dopamine
(1S)-1-(3,3-dimethylbutyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
Substrates: 52% conversion after 3 h
Products: -
Products: -
?
3-(2-aminoethyl)phenol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: -
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + (3,4-dihydroxyphenyl)acetaldehyde
?
-
Substrates: -
Products: -
Products: -
?
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
Substrates: -
Products: -
Products: -
?
5-(2-aminoethyl)-2-methoxyphenol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: -
Products: -
Products: -
?
cyclohexylacetaldehyde + dopamine
(1S)-1-(2-cyclohexylethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
Substrates: 71% conversion after 3 h
Products: -
Products: -
?
dopamine + (1R,4R)-bicyclo[2.2.1]heptane-2,5-dione
(1R,1'S,4R)-6',7'-dihydroxy-3',4'-dihydro-2'H-spiro[bicyclo[2.2.1]heptane-2,1'-isoquinolin]-5-one
-
Substrates: -
Products: -
Products: -
?
dopamine + (2R)-2-methylcyclohexan-1-one
(1S,2R)-2-methyl-3',4'-dihydro-2'H-spiro[cyclohexane-1,1'-isoquinoline]-6',7'-diol
-
Substrates: -
Products: -
Products: -
?
dopamine + 1,3-dihydro-2H-inden-2-one
1,3,3',4'-tetrahydro-2'H-spiro[indene-2,1'-isoquinoline]-6',7'-diol
-
Substrates: -
Products: -
Products: -
?
dopamine + 2-methylcyclohexan-1-one
(1S,2R)-2-methyl-3',4'-dihydro-2'H-spiro[cyclohexane-1,1'-isoquinoline]-6',7'-diol
-
Substrates: -
Products: -
Products: -
?
dopamine + 3,4-dihydronaphthalen-2(1H)-one
(1S)-3,3',4,4'-tetrahydro-1'H,2H-spiro[isoquinoline-1,2'-naphthalene]-6,7-diol
-
Substrates: -
Products: -
Products: -
?
dopamine + 4-biphenylaldehyde
(1S)-1-([1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
Substrates: -
Products: -
Products: -
?
dopamine + 6-bromo-3,4-dihydronaphthalen-2(1H)-one
(1S)-6'-bromo-3,3',4,4'-tetrahydro-1'H,2H-spiro[isoquinoline-1,2'-naphthalene]-6,7-diol
-
Substrates: -
Products: -
Products: -
?
dopamine + 6-chloro-3,4-dihydronaphthalen-2(1H)-one
(1S)-6'-chloro-3,3',4,4'-tetrahydro-1'H,2H-spiro[isoquinoline-1,2'-naphthalene]-6,7-diol
-
Substrates: -
Products: -
Products: -
?
dopamine + 7-methoxy-3,4-dihydronaphthalen-2(1H)-one
(1S)-7'-methoxy-3,3',4,4'-tetrahydro-1'H,2H-spiro[isoquinoline-1,2'-naphthalene]-6,7-diol
-
Substrates: -
Products: -
Products: -
?
dopamine + benzaldehyde
(1S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
Substrates: low activity
Products: -
Products: -
?
dopamine + cyclobutanone
3',4'-dihydro-2'H-spiro[cyclobutane-1,1'-isoquinoline]-6',7'-diol
-
Substrates: -
Products: -
Products: -
?
dopamine + cyclohexane-1,4-dione
6',7'-dihydroxy-3',4'-dihydro-2'H,4H-spiro[cyclohexane-1,1'-isoquinolin]-4-one
-
Substrates: -
Products: -
Products: -
?
dopamine + cyclohexanone
3',4'-dihydro-2'H-spiro[cyclohexane-1,1'-isoquinoline]-6',7'-diol
-
Substrates: -
Products: -
Products: -
?
dopamine + cyclopentanone
3',4'-dihydro-2'H-spiro[cyclopentane-1,1'-isoquinoline]-6',7'-diol
-
Substrates: -
Products: -
Products: -
?
dopamine + oxan-4-one
3,4-dihydro-2H-spiro[isoquinoline-1,4'-oxane]-6,7-diol
-
Substrates: -
Products: -
Products: -
?
dopamine + tert-butyl 3-oxopiperidine-1-carboxylate
tert-butyl (1R)-6,7-dihydroxy-3,4-dihydro-1'H,2H-spiro[isoquinoline-1,3'-piperidine]-1'-carboxylate
-
Substrates: -
Products: -
Products: -
?
dopamine + tert-butyl 4-oxopiperidine-1-carboxylate
tert-butyl 6,7-dihydroxy-3,4-dihydro-1'H,2H-spiro[isoquinoline-1,4'-piperidine]-1'-carboxylate
-
Substrates: -
Products: -
Products: -
?
hydrocinnamaldehyde + dopamine
6,7-dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline
Substrates: molar yield and enantiomeric excess of 6,7-dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline are 86.0 and 95.3%, respectively
Products: -
Products: -
?
naphthalen-1-ylacetaldehyde + dopamine
(1S)-1-[2-(naphthalen-1-yl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
Substrates: 61% conversion after 3 h
Products: -
Products: -
?
phenylacetaldehyde + dopamine
(1S)-1-(2-phenylethyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
Substrates: 51% conversion after 3 h
Products: -
Products: -
?
thiophen-3-ylacetaldehyde + dopamine
(1S)-1-[2-(thiophen-3-yl)ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
Substrates: 68% conversion after 3 h
Products: -
Products: -
?
[4-(trifluoromethoxy)phenyl]acetaldehyde + dopamine
(1S)-1-[2-[4-(trifluoromethoxy)phenyl]ethyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol + H2O
-
Substrates: 65% conversion after 3 h
Products: -
Products: -
?
additional information
?
-
-
Substrates: isozyme NCS1 of Coptis japonica does not catalyze the formation of (S)-norcoclaurine from dopamine and 4-hydroxyphenylacetaldehyde
Products: -
Products: -
?
(S)-norcoclaurine + H2O
dopamine + 4-hydroxyphenylacetaldehyde
Substrates: -
Products: -
Products: -
?
(S)-norcoclaurine + H2O
dopamine + 4-hydroxyphenylacetaldehyde
Substrates: -
Products: -
Products: -
?
(S)-norcoclaurine + H2O
dopamine + 4-hydroxyphenylacetaldehyde
Substrates: -
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
Berberis regeliana
-
Substrates: -
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
Substrates: -
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
Eschscholtzia tenuifolia
-
Substrates: -
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
Eschscholtzia tenuifolia
-
Substrates: 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
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
Eschscholzia pulchella
-
Substrates: -
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
Substrates: -
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
Glaucium rubrum
-
Substrates: -
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
Substrates: -
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
Substrates: -
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
Substrates: -
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
Substrates: -
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
Thalictrum flavum ssp. glaucum
-
Substrates: -
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
Substrates: -
Products: -
Products: -
?
4-(2-aminoethyl)benzene-1,2-diol + 3,4-dihydroxyphenylacetaldehyde
(S)-norlaudanosoline + H2O
-
Substrates: -
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
Substrates: CjNCS1
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
Substrates: CjPR10A
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Eschscholtzia tenuifolia
-
Substrates: -
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Eschscholtzia tenuifolia
-
Substrates: i.e. dopamine + 4-hydroxyphenylacetaldehyde, , 4-hydroxyphenylacetaldehyde can be substituted by 3,4-dihydroxyphenylacetaldehyde but not by 3,4-dihydroxyphenylpyruvate, 4-hydroxyphenylpyruvate or phenylpyruvate
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
Substrates: 4-(2-aminoethyl)benzene-1,2-diol is dopmaine
Products: -
Products: -
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
Substrates: first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
Products: -
Products: -
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
Substrates: 4-(2-aminoethyl)benzene-1,2-diol is dopmaine
Products: -
Products: -
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
Substrates: first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
Products: -
Products: -
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
Substrates: the enzyme is involved in the plants secondary metabolism and is required for the production of bioactive secondary metabolites like morphine
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
Substrates: -
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Substrates: -
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
Substrates: -
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Thalictrum flavum ssp. glaucum
-
Substrates: 4-(2-aminoethyl)benzene-1,2-diol is dopmaine
Products: -
Products: -
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Thalictrum flavum ssp. glaucum
-
Substrates: 4-(2-aminoethyl)benzene-1,2-diol is dopmaine, cooperativity between the dopamine binding sites on each subunit
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Thalictrum flavum ssp. glaucum
-
Substrates: first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
Products: -
Products: -
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Thalictrum flavum ssp. glaucum
-
Substrates: first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Berberis regeliana
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Eschscholtzia tenuifolia
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Eschscholzia pulchella
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Glaucium rubrum
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
Substrates: 4-(2-aminoethyl)benzene-1,2-diol, i.e. dopamine
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
Substrates: 4-(2-aminoethyl)benzene-1,2-diol, i.e. dopamine
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
Substrates: 4-(2-aminoethyl)benzene-1,2-diol, i.e. dopamine
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
Substrates: stereospecific formation of the (S)-norcolaurine enantiomer by the recombinant enzyme, overview
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
Substrates: 4-(2-aminoethyl)benzene-1,2-diol, i.e. dopamine
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
Substrates: -
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
Substrates: -
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: the enzyme is involved in the biosynthesis of benzylisoquinoline
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: -
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: the enzyme catalyzes the stereoselective Pictet-Spengler reaction between dopamine and 4-hydroxyphenylacetaldehyde as a step of benzylisoquinoline alkaloid synthesis in plants
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: -
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Corydalis chinensis
-
Substrates: the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Corydalis chinensis
-
Substrates: -
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: the enzyme is involved in the biosynthesis of benzylisoquinoline
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: -
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
Substrates: the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
Substrates: -
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: the enzyme is involved in the biosynthesis of benzylisoquinoline
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: -
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: -
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
Substrates: 60% conversion after 3 h
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: -
Products: -
Products: -
?
dopamine + 4-hydroxyphenylacetaldehyde
(S)-norcoclaurine + H2O
-
Substrates: -
Products: -
Products: -
?
dopamine + 4-hydroxyphenylacetaldehyde
(S)-norcoclaurine + H2O
-
Substrates: -
Products: -
Products: -
?
dopamine + 4-hydroxyphenylacetaldehyde
(S)-norcoclaurine + H2O
Substrates: -
Products: -
Products: -
?
dopamine + 4-hydroxyphenylacetaldehyde
(S)-norcoclaurine + H2O
-
Substrates: -
Products: -
Products: -
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(S)-norcoclaurine + H2O
dopamine + 4-hydroxyphenylacetaldehyde
Substrates: -
Products: -
Products: -
?
(S)-norcoclaurine + H2O
dopamine + 4-hydroxyphenylacetaldehyde
Substrates: -
Products: -
Products: -
?
(S)-norcoclaurine + H2O
dopamine + 4-hydroxyphenylacetaldehyde
Substrates: -
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
Substrates: first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
Products: -
Products: -
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
Substrates: first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
Products: -
Products: -
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
Substrates: the enzyme is involved in the plants secondary metabolism and is required for the production of bioactive secondary metabolites like morphine
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Substrates: -
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
-
Substrates: -
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Thalictrum flavum ssp. glaucum
-
Substrates: first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
Products: -
Products: -
ir
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
Thalictrum flavum ssp. glaucum
-
Substrates: first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Berberis regeliana
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Eschscholtzia tenuifolia
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Eschscholzia pulchella
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
Glaucium rubrum
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
-
Substrates: initial reaction in isoquinoline biosynthesis
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
Substrates: 4-(2-aminoethyl)benzene-1,2-diol, i.e. dopamine
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
Substrates: 4-(2-aminoethyl)benzene-1,2-diol, i.e. dopamine
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
Substrates: 4-(2-aminoethyl)benzene-1,2-diol, i.e. dopamine
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
-
Substrates: stereospecific formation of the (S)-norcolaurine enantiomer by the recombinant enzyme, overview
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
Substrates: -
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
Substrates: -
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: the enzyme is involved in the biosynthesis of benzylisoquinoline
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: the enzyme catalyzes the stereoselective Pictet-Spengler reaction between dopamine and 4-hydroxyphenylacetaldehyde as a step of benzylisoquinoline alkaloid synthesis in plants
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Corydalis chinensis
-
Substrates: the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: the enzyme is involved in the biosynthesis of benzylisoquinoline
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
Substrates: the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: the enzyme is involved in the biosynthesis of benzylisoquinoline
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
-
Substrates: 60% conversion after 3 h
Products: -
Products: -
?
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
Substrates: the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
Products: -
Products: -
?
dopamine + 4-hydroxyphenylacetaldehyde
(S)-norcoclaurine + H2O
-
Substrates: -
Products: -
Products: -
?
dopamine + 4-hydroxyphenylacetaldehyde
(S)-norcoclaurine + H2O
-
Substrates: -
Products: -
Products: -
?
dopamine + 4-hydroxyphenylacetaldehyde
(S)-norcoclaurine + H2O
Substrates: -
Products: -
Products: -
?
dopamine + 4-hydroxyphenylacetaldehyde
(S)-norcoclaurine + H2O
-
Substrates: -
Products: -
Products: -
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
Thalictrum flavum ssp. glaucum
-
the enzyme is not affected by divalent cations
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
fungal elicitor of Bortrytis sp.
-
isolated elicitor induces the enzyme activity in cell suspension culture 20fold
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
14.6
4-biphenylaldehyde
mutant enzyme L68T/M97V, at pH 7.5 and 30°C
-
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
Thalictrum flavum ssp. glaucum
-
sigmoidal saturation kinetics for dopamine, cooperativity between the dopamine binding sites on each subunit
-
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
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
0.002
4-biphenylaldehyde
mutant enzyme L68T/M97V, at pH 7.5 and 30°C
-
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
140
4-biphenylaldehyde
mutant enzyme L68T/M97V, at pH 7.5 and 30°C
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5 - 7
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
45 - 55
50
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37 - 57
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Thalictrum flavum ssp. glaucum
Thalictrum flavum ssp. glaucum
i.e. meadow rue, 4 isoelectrically different isozymes
-
-
brenda
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
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 is involved in the biosynthetic of benzylisoquinoline
metabolism
-
the enzyme is involved in biosynthesis of benzylisoquinoline alkaloids
metabolism
the enzyme catalyzes the enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
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 catalyzes the stereoselective Pictet-Spengler reaction between dopamine and 4-hydroxyphenylacetaldehyde as a step of benzylisoquinoline alkaloid synthesis in plants
metabolism
the enzyme is involved in the biosynthesis of benzylisoquinoline
metabolism
the enzyme is involved in the biosynthesis of benzylisoquinoline
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 enantioselective Pictet-Spengler condensation of dopamine and 4-hydroxyphenylacetaldehyde as a step in benzylisoquinoline alkaloid biosynthesis
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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_PAPSO
231
1
26015
Swiss-Prot
other Location (Reliability: 1)
NCS2_PAPSO
231
1
26001
Swiss-Prot
Secretory Pathway (Reliability: 2)
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
21180
-
mass spectrometry of recombinant Delta29NCS (coding for amino acids 30210 of NCS)
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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°
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
L68S
the mutant displays good activity toward benzaldehyde and reduced activity with 4-bipenzaldehyde compared to the wild type enzyme
L68T
the mutant displays good activity toward benzaldehyde and increased activity with 4-bipenzaldehyde compared to the wild type enzyme
L68T/M97V
the mutant shows improved activity compared to the wild type enzyme. The mutant shows higher catalytic performance (more than 96% conversion) toward benzaldehyde and dopamine over the wild type enzyme, and also catalyzes the Pictet-Spengler reaction of 4-biphenylaldehyde and dopamine with high conversion (more than 99%) for the effective synthesis of 1-aryl-tetrahydroisoquinoline alkaloids
L72P
the mutant displays good activity toward benzaldehyde and increased activity with 4-bipenzaldehyde compared to the wild type enzyme
M97V
the mutant displays good activity toward benzaldehyde and strongly increased activity with 4-bipenzaldehyde compared to the wild type enzyme
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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80C, purified enzyme, 7 days, no loss of activity
4C, purified enzyme, 7 days, 75% loss of activity
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21(DE3) cells
expressed in Escherichia coli ER2566 pLysS 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
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
elicitor-induced cell cultures show increasing expression of NCS after 2 to 100 hours
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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 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
synthesis
the enzyme has also shown great potential as a biocatalyst for the formation of chiral isoquinolines
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 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 is a highly suitable catalyst for the Pictet-Spengler reaction
synthesis
the enzyme is a highly suitable catalyst for the Pictet-Spengler reaction
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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, Eschscholtzia tenuifolia, Eschscholzia pulchella, Fumaria officinalis, Glaucium rubrum, Lamprocapnos spectabilis, 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
Stadler, R.M.; Zenk, M.H.
A revision of the generally accepted pathway for the biosynthesis of the benzyltetrahydroisoquinoline alkaloid reticuline
Liebigs Ann. Chem.
1990
555-562
1990
Berberis stolonifera
-
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)
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)
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)
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)
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
Argemone mexicana (D2SMN1), Argemone mexicana (D2SMN3), Corydalis saxicola (F5C449), Papaver bracteatum (C3SBT7)
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)
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
Corydalis chinensis, Nandina domestica, Papaver somniferum (Q4QTJ2), Papaver somniferum (Q4QTJ1), Thalictrum flavum (Q67A25)
brenda
Zhao, J.; Mendez-Sanchez, D.; Roddan, R.; Ward, J.; Hailes, H.
Norcoclaurine synthase-mediated stereoselective synthesis of 1,1-disubstituted, spiro- and bis-tetrahydroisoquinoline alkaloids
ACS Catal.
11
131-138
2021
Thalictrum flavum
-
brenda
Zhang, M.; Huang, Z.Y.; Su, Y.; Chen, F.F.; Chen, Q.; Xu, J.H.; Zheng, G.W.
Engineering a norcoclaurine synthase for one-step synthesis of (S)-1-aryl-tetrahydroisoquinolines
Bioresour. Bioprocess.
10
15
2023
Thalictrum flavum (Q67A25)
brenda
Zhang, S.; Zhang, C.; Guo, A.; Liu, B.; Su, H.; Sheng, X.
Computationalmechanistic investigation of the kinetic resolution of alpha-methyl-phenylacetaldehyde by norcoclaurine synthase
Commun. Chem.
7
64
2024
Thalictrum flavum
brenda
Bonamore, A.; Barba, M.; Botta, B.; Boffi, A.; Macone, A.
Norcoclaurine synthase mechanism of an enantioselective Pictet-Spengler catalyzing enzyme
Molecules
15
2070-2078
2010
Thalictrum flavum
brenda
De Sousa, J.P.M.; Oliveira, N.C.S.A.; Fernandes, P.A.
Rational engineering of (S)-norcoclaurine synthase for efficient benzylisoquinoline alkaloids biosynthesis
Molecules
28
4265
2023
Papaver somniferum (Q4QTJ1)
brenda
Stadler, R.; Kutchan, T.; Zenk, M.
(S)-norcoclaurine is the central intermediate in benzylisoquinoline alkaloid biosynthesis
Phytochemistry
28
1083-1086
1989
Berberis stolonifera
-
brenda
Liscombe, D.K.; MacLeod, B.P.; Loukanina, N.; Nandi, O.I.; Facchini, P.J.
Evidence for the monophyletic evolution of benzylisoquinoline alkaloid biosynthesis in angiosperms
Phytochemistry
66
2501-2520
2005
Papaver somniferum (Q4QTJ2), Papaver somniferum (Q4QTJ1), Thalictrum flavum (Q67A25)
brenda
EXTERNAL LINKS (specific for EC-Number 3.5.99.14)
html completed
Use of this online version of BRENDA is free under the CC BY 4.0 license. See terms of use for full details.
Release 2026.1 (March 2026)
About BRENDA
Social media
Help
Survey
Download
Contribution
Legal
Curated at
Member of
![DSMZ Digital Diversity]()
![Global Core Biodata Resource]()
![ELIXIR Core Data Resource]()
![German Network for Bioinformatics Infrastructure]()
