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Literature summary extracted from

  • Samanani, N.; Facchini, P.J.
    Isolation and partial characterization of norcoclaurine synthase, the first committed step in benzylisoquinoline alkaloid biosynthesis, from opium poppy (2001), Planta, 213, 898-906.
    View publication on PubMed

Activating Compound

EC Number Activating Compound Comment Organism Structure
4.2.1.78 fungal elicitor of Bortrytis sp. isolated elicitor induces the enzyme activity in cell suspension culture 20fold Papaver somniferum
4.2.1.78 additional information enzyme is not affected by Mg2+ and Ca2+ Papaver somniferum

Inhibitors

EC Number Inhibitors Comment Organism Structure
4.2.1.78 additional information no inhibition by several benzylisochinoline alkaloids, enzyme is not affected by Mg2+ and Ca2+ Papaver somniferum

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
4.2.1.78 additional information
-
 additional information kinetics, sigmoidal saturation kinetics for dopamine, Hill coeffcient 1.84, cooperativity between the dopamine binding sites on each subunit Papaver somniferum
4.2.1.78 additional information
-
 additional information kinetics, sigmoidal saturation kinetics for dopamine, Hill coeffcient 2.16, cooperativity between the dopamine binding sites on each subunit Thalictrum flavum ssp. glaucum
4.2.1.78 additional information
-
 additional information kinetics, sigmoidal saturation kinetics for dopamine, Hill coeffcient 2.19, cooperativity between the dopamine binding sites on each subunit Eschscholzia californica
4.2.1.78 0.42
-
 4-hydroxyphenylacetaldehyde pH 7.0, 37°C, hyperbolic saturation kinetics Thalictrum flavum ssp. glaucum
4.2.1.78 0.66
-
 4-hydroxyphenylacetaldehyde pH 7.0, 37°C, hyperbolic saturation kinetics Eschscholzia californica
4.2.1.78 1
-
 4-hydroxyphenylacetaldehyde pH 7.0, 37°C, hyperbolic saturation kinetics Papaver somniferum

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.1.78 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde Eschscholzia californica first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux (S)-Norcoclaurine + H2O
-
 ir
4.2.1.78 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde Papaver somniferum first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux (S)-Norcoclaurine + H2O
-
 ir
4.2.1.78 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde 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 (S)-Norcoclaurine + H2O
-
 ir

Organism

EC Number Organism UniProt Comment Textmining
4.2.1.78 Eschscholzia californica
-
-
-
4.2.1.78 no activity in Catharanthus roseus
-
-
-
4.2.1.78 no activity in Nicotiana tabacum
-
-
-
4.2.1.78 Papaver somniferum
-
 cv. Marianne
-
4.2.1.78 Thalictrum flavum ssp. glaucum
-
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
4.2.1.78 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 Eschscholzia californica
a
4.2.1.78 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 Papaver somniferum
a
4.2.1.78 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
a

Source Tissue

EC Number Source Tissue Comment Organism Textmining
4.2.1.78 cell suspension culture
-
 Eschscholzia californica
-
4.2.1.78 cell suspension culture
-
 Papaver somniferum
-
4.2.1.78 cell suspension culture
-
 Thalictrum flavum ssp. glaucum
-
4.2.1.78 plant all organs especially in root and stem Papaver somniferum
-
4.2.1.78 root highest activity level Papaver somniferum
-
4.2.1.78 seed germinating Papaver somniferum
-
4.2.1.78 seedling
-
 Papaver somniferum
-
4.2.1.78 stem
-
 Papaver somniferum
-

Storage Stability

EC Number Storage Stability Organism
4.2.1.78 -80°C, purified enzyme, 7 days, no loss of activity Papaver somniferum
4.2.1.78 4°C, purified enzyme, 7 days, 75% loss of activity Papaver somniferum

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.1.78 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde 4-(2-aminoethyl)benzene-1,2-diol is dopmaine Eschscholzia californica (S)-Norcoclaurine + H2O
-
 ir
4.2.1.78 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde 4-(2-aminoethyl)benzene-1,2-diol is dopmaine Papaver somniferum (S)-Norcoclaurine + H2O
-
 ir
4.2.1.78 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde 4-(2-aminoethyl)benzene-1,2-diol is dopmaine Thalictrum flavum ssp. glaucum (S)-Norcoclaurine + H2O
-
 ir
4.2.1.78 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux Eschscholzia californica (S)-Norcoclaurine + H2O
-
 ir
4.2.1.78 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux Papaver somniferum (S)-Norcoclaurine + H2O
-
 ir
4.2.1.78 4-(2-Aminoethyl)benzene-1,2-diol + 4-hydroxyphenylacetaldehyde first step of benzylisoquinoline alkaloid synthesis, enzyme might play a regulatory or rate-limiting role in controlling the rate of pathway flux Thalictrum flavum ssp. glaucum (S)-Norcoclaurine + H2O
-
 ir

Synonyms

EC Number Synonyms Comment Organism
4.2.1.78 NCS
-
 Eschscholzia californica
4.2.1.78 NCS
-
 Papaver somniferum
4.2.1.78 NCS
-
 Thalictrum flavum ssp. glaucum
4.2.1.78 norcoclaurine synthase
-
 Eschscholzia californica
4.2.1.78 norcoclaurine synthase
-
 Papaver somniferum
4.2.1.78 norcoclaurine synthase
-
 Thalictrum flavum ssp. glaucum

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
4.2.1.78 45 55
-
 Eschscholzia californica
4.2.1.78 45 55
-
 Thalictrum flavum ssp. glaucum
4.2.1.78 50
-
-
 Papaver somniferum

Temperature Range [°C]

EC Number Temperature Minimum [°C] Temperature Maximum [°C] Comment Organism
4.2.1.78 37 57 half-maximal activities at 37°C and 57°C Papaver somniferum

Temperature Stability [°C]

EC Number Temperature Stability Minimum [°C] Temperature Stability Maximum [°C] Comment Organism
4.2.1.78 55
-
 instable above 55°C Papaver somniferum

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
4.2.1.78 6.5 7
-
 Eschscholzia californica
4.2.1.78 6.5 7
-
 Papaver somniferum
4.2.1.78 6.5 7
-
 Thalictrum flavum ssp. glaucum

pH Range

EC Number pH Minimum pH Maximum Comment Organism
4.2.1.78 6.2 9 50% of maximal activity at pH 6.2, 68% of maximal activity at pH 9.0 Papaver somniferum