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Literature summary extracted from

  • 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 (2014), Biosci. Biotechnol. Biochem., 78, 701-707 .
    View publication on PubMed

Application

EC Number Application Comment Organism
4.2.1.78 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 Coptis japonica

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.2.1.78 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 Coptis japonica

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 + dopamine Coptis japonica the enzyme catalyzes the stereoselective Pictet-Spengler reaction between dopamine and 4-hydroxyphenylacetaldehyde as a step of benzylisoquinoline alkaloid synthesis in plants (S)-norcoclaurine + H2O
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 ?

Organism

EC Number Organism UniProt Comment Textmining
4.2.1.78 Coptis japonica A2A1A1
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-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.1.78 1-butylaldehyde + dopamine molar yield and enantiomeric excess of 6,7-dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline are 99.6 and 98.0 %, respectively Coptis japonica 6,7-dihydroxy-1-propyl-1,2,3,4-tetrahydroisoquinoline
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 ?
4.2.1.78 4-hydroxyphenylacetaldehyde + dopamine
-
 Coptis japonica (S)-norcoclaurine + H2O
-
 ?
4.2.1.78 4-hydroxyphenylacetaldehyde + dopamine the enzyme catalyzes the stereoselective Pictet-Spengler reaction between dopamine and 4-hydroxyphenylacetaldehyde as a step of benzylisoquinoline alkaloid synthesis in plants Coptis japonica (S)-norcoclaurine + H2O
-
 ?
4.2.1.78 hydrocinnamaldehyde + dopamine molar yield and enantiomeric excess of 6,7-dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline are 86.0 and 95.3%, respectively Coptis japonica 6,7-dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline
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 ?

Synonyms

EC Number Synonyms Comment Organism
4.2.1.78 CjPR10A
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 Coptis japonica

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
4.2.1.78 30
-
 assay at Coptis japonica

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
4.2.1.78 7
-
 assay at Coptis japonica

General Information

EC Number General Information Comment Organism
4.2.1.78 metabolism the enzyme catalyzes the stereoselective Pictet-Spengler reaction between dopamine and 4-hydroxyphenylacetaldehyde as a step of benzylisoquinoline alkaloid synthesis in plants Coptis japonica