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ENZYME

ENZYME entry: EC 1.14.16.1

PURL: https://purl.expasy.org/enzyme/EC/1.14.16.1
Accepted Name
phenylalanine 4-monooxygenase
Alternative Name(s)
PAH
phenylalaninase
phenylalanine 4-hydroxylase
phenylalanine hydroxylase
Reaction catalysed
(6R)-L-erythro-5,6,7,8-tetrahydrobiopterin + L-phenylalanine + O2 = (4aS,6R)-4a-hydroxy-L-erythro-5,6,7,8-tetrahydrobiopterin + L-tyrosine
Comment(s)
  • The reaction involves an arene oxide which rearranges to give the phenolic hydroxy group.
  • This results in the hydrogen at C-4 migrating to C-3 and in part being retained, a process known as the NIH-shift.
  • The 4a-hydroxytetrahydrobiopterin formed can dehydrate to 6,7- dihydrobiopterin, both spontaneously and by the action of EC 4.2.1.96.
  • The 6,7-dihydrobiopterin can be enzymically reduced back to tetrahydrobiopterin, by EC 1.5.1.34, or slowly rearranges into the more stable compound 7,8-dihydrobiopterin.
  • Formerly EC 1.14.3.1 and EC 1.99.1.2.
Cross-references
BRENDA1.14.16.1
EC2PDB1.14.16.1
ExplorEnz1.14.16.1
KEGG Ligand Database for Enzyme Nomenclature1.14.16.1
IUBMB Enzyme Nomenclature1.14.16.1
MEDLINEFind literature relating to 1.14.16.1
MetaCyc1.14.16.1
Rhea expert-curated reactions1.14.16.1
UniProtKB/Swiss-Prot
Q2KIH7, PH4H_BOVINP90925, PH4H_CAEELQ9A7V7, PH4H_CAUVC
A8HQD7, PH4H_CHLREP30967, PH4H_CHRVOQ54XS1, PH4H_DICDI
P17276, PH4H_DROMEP00439, PH4H_HUMANP16331, PH4H_MOUSE
E5KBU4, PH4H_PHYPAE5KBU3, PH4H_PINTAP43334, PH4H_PSEAE
Q8XU39, PH4H_RALN1P04176, PH4H_RATQ98D72, PH4H_RHILO
Q9KLB8, PH4H_VIBCH

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