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Literature summary extracted from

  • 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 (2010), Green Chem., 12, 1623-1627.
No PubMed abstract available

Application

EC Number Application Comment Organism
4.2.1.78 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 Thalictrum flavum

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.2.1.78 recombinant expression of C-terminally His-tagged NCS in Eschericha coli strain BL21(DE3) Thalictrum flavum

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.1.78 4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol Thalictrum flavum stereospecific formation of the (S)-norcolaurine enantiomer by the recombinant enzyme, overview (S)-norcoclaurine + H2O
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 ?

Organism

EC Number Organism UniProt Comment Textmining
4.2.1.78 Thalictrum flavum
-
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
4.2.1.78 recombinant C-terminally His-tagged NCS from Eschericha coli strain BL21(DE3) by nickel affinity chromatography Thalictrum flavum

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.1.78 4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol 4-(2-aminoethyl)benzene-1,2-diol, i.e. dopamine Thalictrum flavum (S)-norcoclaurine + H2O
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 ?
4.2.1.78 4-hydroxyphenylacetaldehyde + 4-(2-aminoethyl)benzene-1,2-diol stereospecific formation of the (S)-norcolaurine enantiomer by the recombinant enzyme, overview Thalictrum flavum (S)-norcoclaurine + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
4.2.1.78 NCS
-
 Thalictrum flavum

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
4.2.1.78 37
-
 assay at Thalictrum flavum

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
4.2.1.78 7
-
 assay at Thalictrum flavum

General Information

EC Number General Information Comment Organism
4.2.1.78 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 Thalictrum flavum