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(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
-
-
?
3-(2-aminoethyl)phenol + 4-hydroxyphenylacetaldehyde
?
-
-
-
-
?
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-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
4-hydroxyphenylacetone + dopamine
1-(4-hydroxybenzyl)-1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
-
-
-
?
5-(2-aminoethyl)-2-methoxyphenol + 4-hydroxyphenylacetaldehyde
?
-
-
-
-
?
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
-
-
-
-
?
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
-
-
-
-
?
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
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
(S)-Norcoclaurine + H2O
4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde
?
4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol
(S)-norcoclaurine + H2O
4-hydroxyphenylacetaldehyde + dopamine
(S)-norcoclaurine + H2O
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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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
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Schumacher, H.M.; Rueffer, M.; Nagakura, N.; Zenk, M.H.
Partial purification and properties of (S)-norlaudanosoline synthase from Eschscholtzia tenuifolia cell cultures
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212-220
1983
Eschscholtzia tenuifolia
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Samanani, N.; Facchini, P.J.
Purification and characterization of norcoclaurine synthase. The first committed enzyme in benzylisoquinoline alkaloid biosynthesis in plants
J. Biol. Chem.
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33878-33883
2002
Thalictrum flavum ssp. glaucum
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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
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2018
Papaver bracteatum (C3SBT7), Papaver bracteatum, Argemone mexicana (D2SMN1), Argemone mexicana (D2SMN3), Argemone mexicana, Corydalis saxicola (F5C449), Corydalis saxicola
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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)
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