Reaction participants Show >> << Hide
- Name help_outline (6R)-L-erythro-5,6,7,8-tetrahydrobiopterin Identifier CHEBI:59560 (Beilstein: 4699705; CAS: 17528-72-2,27070-47-9) 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-phenylalanine Identifier CHEBI:58095 Charge 0 Formula C9H11NO2 InChIKeyhelp_outline COLNVLDHVKWLRT-QMMMGPOBSA-N SMILEShelp_outline [NH3+][C@@H](Cc1ccccc1)C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 74 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 2,709 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 3-hydroxy-L-phenylalanine Identifier CHEBI:78290 Charge 0 Formula C9H11NO3 InChIKeyhelp_outline JZKXXXDKRQWDET-QMMMGPOBSA-N SMILEShelp_outline [NH3+][C@@H](Cc1cccc(O)c1)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:41532 | RHEA:41533 | RHEA:41534 | RHEA:41535 | |
|---|---|---|---|---|
| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
| UniProtKB help_outline |
|
|||
| EC numbers help_outline | ||||
| KEGG help_outline | ||||
| MetaCyc help_outline |
Publications
-
Identification of phenylalanine 3-hydroxylase for meta-tyrosine biosynthesis.
Zhang W., Ames B.D., Walsh C.T.
Phenylalanine hydroxylase (PheH) is an iron(II)-dependent enzyme that catalyzes the hydroxylation of aromatic amino acid l-phenylalanine (L-Phe) to l-tyrosine (L-Tyr). The enzymatic modification has been demonstrated to be highly regiospecific, forming proteinogenic para-Tyr (p-Tyr) exclusively. H ... >> More
Phenylalanine hydroxylase (PheH) is an iron(II)-dependent enzyme that catalyzes the hydroxylation of aromatic amino acid l-phenylalanine (L-Phe) to l-tyrosine (L-Tyr). The enzymatic modification has been demonstrated to be highly regiospecific, forming proteinogenic para-Tyr (p-Tyr) exclusively. Here we biochemically characterized the first example of a phenylalanine 3-hydroxylase (Phe3H) that catalyzes the synthesis of meta-Tyr (m-Tyr) from Phe. Subsequent mutagenesis studies revealed that two residues in the active site of Phe3H (Cys187 and Thr202) contribute to C-3 rather than C-4 hydroxylation of the phenyl ring. This work sets the stage for the mechanistic and structural study of regiospecific control of the substrate hydroxylation by PheH. << Less