EC |
1.14.99.59 |
Accepted name: |
tryptamine 4-monooxygenase |
Reaction: |
tryptamine + reduced acceptor + O2 = 4-hydroxytryptamine + acceptor + H2O |
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For diagram of psilocybin biosynthesis, click here |
Glossary: |
psilocybin = 3-[2-(dimethylamino)ethyl]-1H-indol-4-yl phosphate
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Other name(s): |
PsiH |
Systematic name: |
tryptamine,hydrogen-donor:oxygen oxidoreductase (4-hydroxylating) |
Comments: |
A cytochrome P-450 (heme-thiolate) protein isolated from the fungus Psilocybe cubensis. Involved in the biosynthesis of the psychoactive compound psilocybin. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Fricke, J., Blei, F. and Hoffmeister, D. Enzymatic synthesis of psilocybin. Angew. Chem. Int. Ed. Engl. 56 (2017) 12352–12355. [DOI] [PMID: 28763571] |
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[EC 1.14.99.59 created 2017] |
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EC |
2.1.1.345 |
Accepted name: |
psilocybin synthase |
Reaction: |
2 S-adenosyl-L-methionine + 4-hydroxytryptamine 4-phosphate = 2 S-adenosyl-L-homocysteine + psilocybin (overall reaction) (1a) S-adenosyl-L-methionine + 4-hydroxytryptamine 4-phosphate = S-adenosyl-L-homocysteine + 4-hydroxy-N-methyltryptamine 4-phosphate (1b) S-adenosyl-L-methionine + 4-hydroxy-N-methyltryptamine 4-phosphate = S-adenosyl-L-homocysteine + psilocybin |
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For diagram of psilocybin biosynthesis, click here |
Glossary: |
psilocybin = 3-[2-(dimethylamino)ethyl]-1H-indol-4-yl phosphate |
Other name(s): |
PsiM |
Systematic name: |
S-adenosyl-L-methionine:4-hydroxytryptamine-4-phosphate N,N-dimethyltransferase |
Comments: |
Isolated from the fungus Psilocybe cubensis. The product, psilocybin, is a psychoactive compound. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Fricke, J., Blei, F. and Hoffmeister, D. Enzymatic synthesis of psilocybin. Angew. Chem. Int. Ed. Engl. 56 (2017) 12352–12355. [DOI] [PMID: 28763571] |
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[EC 2.1.1.345 created 2017] |
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EC |
2.7.1.222 |
Accepted name: |
4-hydroxytryptamine kinase |
Reaction: |
ATP + 4-hydroxytryptamine = ADP + 4-hydroxytryptamine 4-phosphate |
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For diagram of psilocybin biosynthesis, click here |
Glossary: |
psilocybin = 3-[2-(dimethylamino)ethyl]-1H-indol-4-yl phosphate |
Other name(s): |
PsiK |
Systematic name: |
ATP:4-hydroxytryptamine 4-phosphotransferase |
Comments: |
Also acts on 4-hydroxy-L-tryptophan in vitro. Isolated from the fungus Psilocybe cubensis. Involved in the biosynthesis of the psychoactive compound psilocybin. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc |
References: |
1. |
Fricke, J., Blei, F. and Hoffmeister, D. Enzymatic synthesis of psilocybin. Angew. Chem. Int. Ed. Engl. 56 (2017) 12352–12355. [DOI] [PMID: 28763571] |
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[EC 2.7.1.222 created 2017] |
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EC |
4.1.1.105 |
Accepted name: |
L-tryptophan decarboxylase |
Reaction: |
L-tryptophan = tryptamine + CO2 |
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For diagram of psilocybin biosynthesis, click here |
Other name(s): |
psiD (gene name); TDC (gene name) |
Systematic name: |
L-tryptophan carboxy-lyase |
Comments: |
The enzyme has been characterized from bacteria, plants, and fungi. Unlike EC 4.1.1.28, aromatic-L-amino-acid decarboxylase, this enzyme is specific for L-tryptophan. |
Links to other databases: |
BRENDA, EXPASY, KEGG, MetaCyc, PDB |
References: |
1. |
Noe, W., Mollenschott, C. and Berlin, J. Tryptophan decarboxylase from Catharanthus roseus cell suspension cultures: purification, molecular and kinetic data of the homogenous protein. Plant Mol. Biol. 3 (1984) 281–288. [DOI] [PMID: 24310513] |
2. |
Buki, K.G., Vinh, D.Q. and Horvath, I. Partial purification and some properties of tryptophan decarboxylase from a Bacillus strain. Acta Microbiol Hung 32 (1985) 65–73. [PMID: 4036551] |
3. |
Nakazawa, H., Kumagai, H. and Yamada, H. Constitutive aromatic L-amino acid decarboxylase from Micrococcus percitreus. Biochem. Biophys. Res. Commun. 61 (1974) 75–82. [DOI] [PMID: 4441405] |
4. |
Lopez-Meyer, M. and Nessler, C.L. Tryptophan decarboxylase is encoded by two autonomously regulated genes in Camptotheca acuminata which are differentially expressed during development and stress. Plant J. 11 (1997) 1167–1175. [DOI] [PMID: 9225462] |
5. |
Fricke, J., Blei, F. and Hoffmeister, D. Enzymatic synthesis of psilocybin. Angew. Chem. Int. Ed. Engl. 56 (2017) 12352–12355. [DOI] [PMID: 28763571] |
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[EC 4.1.1.105 created 2017] |
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