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- Name help_outline (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin Identifier CHEBI:59560 (Beilstein: 4699705; CAS: 27070-47-9,17528-72-2) help_outline Charge 0 Formula C9H15N5O3 InChIKeyhelp_outline FNKQXYHWGSIFBK-RPDRRWSUSA-N SMILEShelp_outline [H][C@@]1(CNc2nc(N)[nH]c(=O)c2N1)[C@@H](O)[C@H](C)O 2D coordinates Mol file for the small molecule Search links Involved in 13 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline L-tryptophan Identifier CHEBI:57912 Charge 0 Formula C11H12N2O2 InChIKeyhelp_outline QIVBCDIJIAJPQS-VIFPVBQESA-N SMILEShelp_outline [NH3+][C@@H](Cc1c[nH]c2ccccc12)C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 56 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline O2 Identifier CHEBI:15379 (CAS: 7782-44-7) help_outline Charge 0 Formula O2 InChIKeyhelp_outline MYMOFIZGZYHOMD-UHFFFAOYSA-N SMILEShelp_outline O=O 2D coordinates Mol file for the small molecule Search links Involved in 2,648 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin Identifier CHEBI:15642 Charge 0 Formula C9H15N5O4 InChIKeyhelp_outline KJKIEFUPAPPGBC-XXKOCQOQSA-N SMILEShelp_outline C1=2[C@@](N[C@H](CN1)[C@H]([C@H](C)O)O)(C(N=C(N2)N)=O)O 2D coordinates Mol file for the small molecule Search links Involved in 5 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 5-hydroxy-L-tryptophan Identifier CHEBI:58266 Charge 0 Formula C11H12N2O3 InChIKeyhelp_outline LDCYZAJDBXYCGN-VIFPVBQESA-N SMILEShelp_outline [NH3+][C@@H](Cc1c[nH]c2ccc(O)cc12)C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
RHEA:16709 | RHEA:16710 | RHEA:16711 | RHEA:16712 | |
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Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Publications
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Three-dimensional structure of human tryptophan hydroxylase and its implications for the biosynthesis of the neurotransmitters serotonin and melatonin.
Wang L., Erlandsen H., Haavik J., Knappskog P.M., Stevens R.C.
Tryptophan hydroxylase oxidizes L-tryptophan to 5-hydroxy-L-tryptophan in the rate-determining step of serotonin biosynthesis. We have determined the X-ray crystal structure (1.7 A) of a truncated functional form of human tryptophan hydroxylase with the bound cofactor analogue 7,8-dihydro-L-biopte ... >> More
Tryptophan hydroxylase oxidizes L-tryptophan to 5-hydroxy-L-tryptophan in the rate-determining step of serotonin biosynthesis. We have determined the X-ray crystal structure (1.7 A) of a truncated functional form of human tryptophan hydroxylase with the bound cofactor analogue 7,8-dihydro-L-biopterin, providing the first atomic-resolution information for the catalytic domain of this important enzyme. Comparison of the three-dimensional structures of all three members of the aromatic amino acid hydroxylase family--tyrosine hydroxylase, phenylalanine hydroxylase, and tryptophan hydroxylase--reveals important differences at the active sites. << Less
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Influence of steric bulk and electrostatics on the hydroxylation regiospecificity of tryptophan hydroxylase: characterization of methyltryptophans and azatryptophans as substrates.
Moran G.R., Phillips R.S., Fitzpatrick P.F.
Tryptophan hydroxylase is a pterin-dependent amino acid hydroxylase that catalyzes the incorporation of one atom of molecular oxygen into tryptophan to form 5-hydroxytryptophan. The substrate specificity and hydroxylation regiospecificity of tryptophan hydroxylase have been investigated using tryp ... >> More
Tryptophan hydroxylase is a pterin-dependent amino acid hydroxylase that catalyzes the incorporation of one atom of molecular oxygen into tryptophan to form 5-hydroxytryptophan. The substrate specificity and hydroxylation regiospecificity of tryptophan hydroxylase have been investigated using tryptophan analogues that have methyl substituents or nitrogens incorporated into the indole ring. The products of the reactions show that the regiospecificity of tryptophan hydroxylase is stringent. Hydroxylation does not occur at the 4 or 6 carbon in response to changes in substrate topology or atomic charge. 5-Hydroxymethyltryptophan and 5-hydroxy-4-methyltryptophan are the products from 5-methyltryptophan. These products establish that the hydroxylating intermediate is sufficiently potent to hydroxylate benzylic carbons and that the direction of the NIH shift in tryptophan hydroxylase is from carbon 5 to carbon 4. The effects on the V/K values for the amino acids indicate that the enzyme is most sensitive to changes at position 5 of the indole ring. The V(max) values for amino acid hydroxylation differ at most by a factor of 3 from that observed for tryptophan, while the efficiencies of hydroxylation with respect to tetrahydropterin consumption vary 6-fold, consistent with oxygen transfer to the amino acid being partially or fully rate limiting in productive catalysis. << Less
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Purification and some properties of bovine pineal tryptophan 5-monooxygenase.
Nukiwa T., Toyama C., Okita C., Kataoka T., Ichiyama A.
Biochem Biophys Res Commun 60:1029-1035(1974) [PubMed] [EuropePMC]