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Literature summary extracted from

  • Blei, F.; Baldeweg, F.; Fricke, J.; Hoffmeister, D.
    Biocatalytic production of psilocybin and derivatives in tryptophan synthase-enhanced reactions (2018), Chemistry, 24, 10028-10031 .
    View publication on PubMed

Application

EC Number Application Comment Organism
4.2.1.20 synthesis use of enzyme in production of psilocybin formation from 4-hydroxyindole and L-serine, and similarly of 7-phosphoryloxytryptamine (isonorbaeocystin), and of serotonin, together with Psilocybe cubensis enzymes PsiD, PsiK, and PsiM, which provide decarboxylase, kinase, and methyltransferase activity, respectively Psilocybe cubensis
4.2.1.122 synthesis the enzyme participates in psilocybin formation from 4-hydroxyindole and L-serine, which are less cost-intensive substrates, compared to the previous method. The pharmaceutical interest in this psychotropic natural product as a future medication to treat depression and anxiety is strongly reemerging. Enzymatic production of 7-phosphoryloxytryptamine (isonorbaeocystin), a non-natural congener of the Psilocybe alkaloid norbaeocystin (4-phosphoryloxytryptamine), and of serotonin (5-hydroxytryptamine) by means of the same in vitro approach Psilocybe cubensis

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.2.1.122 recombinant expression of N-terminally His6-tagged TrpB in Escherichia coli strain KRX Psilocybe cubensis

Protein Variants

EC Number Protein Variants Comment Organism
4.2.1.122 additional information biocatalytic production of psilocybin and derivatives in tryptophan synthase-enhanced reactions, in vitro reconstituted indole alkaloid synthesis pathway including enzyme PsiD, PsiK and PsiM, and ATP and S-adenosyl-L-methionine, method, overview. Assays run only with TrpB and PsiD result in identical chromatograms Psilocybe cubensis

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
4.2.1.20 0.016
-
 4-hydroxyindole pH 7.0, 30°C Psilocybe cubensis
4.2.1.20 0.04
-
 indole pH 7.0, 30°C Psilocybe cubensis
4.2.1.20 2.9
-
 L-serine pH 7.0, 30°C Psilocybe cubensis
4.2.1.122 additional information
-
 additional information Michaelis-Menten kinetics Psilocybe cubensis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.1.122 L-serine + indole Psilocybe cubensis
-
 L-tryptophan + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.1.1.345 Psilocybe cubensis P0DPA9
-
-
4.2.1.20 Psilocybe cubensis A0A2U8JPY3
-
-
4.2.1.122 Psilocybe cubensis A0A2U8JPY3
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.1.1.345 2 S-adenosyl-L-methionine + 4-hydroxytryptamine 4-phosphate the enzyme is strictly specific. It cannot tolerate a 7-phosphoryloxy-substituted compounds as acceptor substrate Psilocybe cubensis 2 S-adenosyl-L-homocysteine + psilocybin
-
 ?
4.2.1.20 L-serine + 4-hydroxyindole
-
 Psilocybe cubensis 4-hydroxytryptophan + H2O
-
 ?
4.2.1.20 L-serine + 5-hydroxyindole
-
 Psilocybe cubensis 5-hydroxytryptophan + H2O
-
 ?
4.2.1.20 L-serine + 7-hydroxyindole
-
 Psilocybe cubensis 7-hydroxytryptophan + H2O
-
 ?
4.2.1.20 L-serine + indole
-
 Psilocybe cubensis tryptophan + H2O
-
 ?
4.2.1.20 additional information no substrate: 6-hydroxyindole Psilocybe cubensis ?
-
 ?
4.2.1.122 L-serine + 4-hydroxyindole
-
 Psilocybe cubensis 4-hydroxy-L-tryptophan + H2O
-
 ?
4.2.1.122 L-serine + 5-hydroxyindole
-
 Psilocybe cubensis 5-hydroxy-L-tryptophan + H2O
-
 ?
4.2.1.122 L-serine + 7-hydroxyindole
-
 Psilocybe cubensis 7-hydroxy-L-tryptophan + H2O
-
 ?
4.2.1.122 L-serine + indole
-
 Psilocybe cubensis L-tryptophan + H2O
-
 ?
4.2.1.122 L-serine + indole L-serine is the preferred substrate Psilocybe cubensis L-tryptophan + H2O
-
 ?
4.2.1.122 additional information enzymatic production of psilocybin formation from 4-hydroxyindole and L-serine and of 7-phosphoryloxytryptamine (isonorbaeocystin), a non-natural congener of the Psilocybe alkaloid norbaeocystin (4-phosphoryloxytryptamine), and of serotonin (5-hydroxytryptamine) by means of the same in vitro approach, overview Psilocybe cubensis ?
-
 ?

Subunits

EC Number Subunits Comment Organism
4.2.1.20 ? x * 75500, calculated from sequence Psilocybe cubensis
4.2.1.122 monomer 1 * 75500, about, TrpB monomer, sequence calculation Psilocybe cubensis

Synonyms

EC Number Synonyms Comment Organism
2.1.1.345 PsiM
-
 Psilocybe cubensis
4.2.1.20 trpB
-
 Psilocybe cubensis
4.2.1.122 TrpBbeta
-
 Psilocybe cubensis

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
4.2.1.20 30
-
-
 Psilocybe cubensis
4.2.1.122 30
-
 recombinant enzyme Psilocybe cubensis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
4.2.1.20 8
-
-
 Psilocybe cubensis
4.2.1.122 8
-
 recombinant enzyme Psilocybe cubensis

pI Value

EC Number Organism Comment pI Value Maximum pI Value
4.2.1.20 Psilocybe cubensis calculated from sequence
-
 5.9
4.2.1.122 Psilocybe cubensis TrpB monomer, sequence calculation
-
 5.9

General Information

EC Number General Information Comment Organism
4.2.1.122 physiological function the enzyme is part of the tryptophan synthase complex. Indole formation is catalyzed by the alpha-subunit (TrpBalpha), L-tryptophan production is catalyzed by the beta-subunit (TrpBbeta) Psilocybe cubensis