Mechanism of Aromatic Amino Acid Hydroxylation

Overview

Journal Biochemistry

Specialty Biochemistry

Date 2003 Dec 4

PMID 14640675

Citations 95

Authors

Paul F Fitzpatrick

Affiliations

Soon will be listed here.

Citing Articles

An insight into role of amino acids as antioxidants via NRF2 activation.

Egbujor M, Olaniyan O, Emeruwa C, Saha S, Saso L, Tucci P Amino Acids. 2024; 56(1):23.

PMID: 38506925 PMC: 10954862. DOI: 10.1007/s00726-024-03384-8.

Mechanism of Benzene Hydroxylation on Tri-Iron Oxo-Centered Cluster-Based Metal-Organic Frameworks.

Vitillo J, Choudhary M, Simons M, Gagliardi L, Bhan A J Phys Chem C Nanomater Interfaces. 2023; 127(48):23246-23257.

PMID: 38090139 PMC: 10711795. DOI: 10.1021/acs.jpcc.3c06423.

ASCL1 Is Involved in the Pathogenesis of Schizophrenia by Regulation of Genes Related to Cell Proliferation, Neuronal Signature Formation, and Neuroplasticity.

Abashkin D, Karpov D, Kurishev A, Marilovtseva E, Golimbet V Int J Mol Sci. 2023; 24(21).

PMID: 37958729 PMC: 10648210. DOI: 10.3390/ijms242115746.

The A328 V/E (rs2887147) polymorphisms in human tryptophan hydroxylase 2 compromise enzyme activity.

Carkaci-Salli N, Bewley M, Tekin I, Flanagan J, Vrana K Biochem Biophys Rep. 2023; 35:101527.

PMID: 37608910 PMC: 10440358. DOI: 10.1016/j.bbrep.2023.101527.

Semi-Rational Design of L-Isoleucine Dioxygenase Generated Its Activity for Aromatic Amino Acid Hydroxylation.

An J, Guan J, Nie Y Molecules. 2023; 28(9).

PMID: 37175159 PMC: 10180240. DOI: 10.3390/molecules28093750.

References

Balasubramanian S, Carr R, Bender C, Peisach J, Benkovic S . Identification of metal ligands in Cu(II)-inhibited Chromobacterium violaceum phenylalanine hydroxylase by electron spin echo envelope modulation analysis of histidine to serine mutations. Biochemistry. 1994; 33(28):8532-7. DOI: 10.1021/bi00194a019. View

Andersen O, Flatmark T, Hough E . Crystal structure of the ternary complex of the catalytic domain of human phenylalanine hydroxylase with tetrahydrobiopterin and 3-(2-thienyl)-L-alanine, and its implications for the mechanism of catalysis and substrate activation. J Mol Biol. 2002; 320(5):1095-108. DOI: 10.1016/s0022-2836(02)00560-0. View

Ellis H, McCusker K, Fitzpatrick P . Use of a tyrosine hydroxylase mutant enzyme with reduced metal affinity allows detection of activity with cobalt in place of iron. Arch Biochem Biophys. 2002; 408(2):305-7. DOI: 10.1016/s0003-9861(02)00568-4. View

ELLIS H, Daubner S, McCulloch R, FITZPATRICK P . Phenylalanine residues in the active site of tyrosine hydroxylase: mutagenesis of Phe300 and Phe309 to alanine and metal ion-catalyzed hydroxylation of Phe300. Biochemistry. 1999; 38(34):10909-14. DOI: 10.1021/bi991160u. View

Dickson P, Jennings I, Cotton R . Delineation of the catalytic core of phenylalanine hydroxylase and identification of glutamate 286 as a critical residue for pterin function. J Biol Chem. 1994; 269(32):20369-75. View

Davis M, Kaufman S . Evidence for the formation of the 4a-carbinolamine during the tyrosine-dependent oxidation of tetrahydrobiopterin by rat liver phenylalanine hydroxylase. J Biol Chem. 1989; 264(15):8585-96. View

Schunemann V, Meier C, Meyer-Klaucke W, Winkler H, Trautwein A, Knappskog P . Iron coordination geometry in full-length, truncated, and dehydrated forms of human tyrosine hydroxylase studied by Mössbauer and X-ray absorption spectroscopy. J Biol Inorg Chem. 1999; 4(2):223-31. DOI: 10.1007/s007750050308. View

Hegg E, Que Jr L . The 2-His-1-carboxylate facial triad--an emerging structural motif in mononuclear non-heme iron(II) enzymes. Eur J Biochem. 1998; 250(3):625-9. DOI: 10.1111/j.1432-1033.1997.t01-1-00625.x. View

Grapperhaus C, Mienert B, Bill E, Weyhermuller T, Wieghardt K . Mononuclear (nitrido)iron(V) and (oxo)iron(IV) complexes via photolysis of [(cyclam-acetato)FeIII(N3)]+ and ozonolysis of [(cyclam-acetato)FeIII(O3SCF3)]+ in water/acetone mixtures. Inorg Chem. 2001; 39(23):5306-17. DOI: 10.1021/ic0005238. View

10.

Andersen O, Flatmark T, Hough E . High resolution crystal structures of the catalytic domain of human phenylalanine hydroxylase in its catalytically active Fe(II) form and binary complex with tetrahydrobiopterin. J Mol Biol. 2001; 314(2):279-91. DOI: 10.1006/jmbi.2001.5061. View

11.

Schofield C, Zhang Z . Structural and mechanistic studies on 2-oxoglutarate-dependent oxygenases and related enzymes. Curr Opin Struct Biol. 1999; 9(6):722-31. DOI: 10.1016/s0959-440x(99)00036-6. View

12.

Fitzpatrick P, Ralph E, Ellis H, Willmon O, Daubner S . Characterization of metal ligand mutants of tyrosine hydroxylase: insights into the plasticity of a 2-histidine-1-carboxylate triad. Biochemistry. 2003; 42(7):2081-8. DOI: 10.1021/bi0271493. View

13.

FITZPATRICK P . Studies of the rate-limiting step in the tyrosine hydroxylase reaction: alternate substrates, solvent isotope effects, and transition-state analogues. Biochemistry. 1991; 30(26):6386-91. DOI: 10.1021/bi00240a006. View

14.

Sono M, Roach M, Coulter E, Dawson J . Heme-Containing Oxygenases. Chem Rev. 1996; 96(7):2841-2888. DOI: 10.1021/cr9500500. View

15.

ELLIS H, Daubner S, FITZPATRICK P . Mutation of serine 395 of tyrosine hydroxylase decouples oxygen-oxygen bond cleavage and tyrosine hydroxylation. Biochemistry. 2000; 39(14):4174-81. DOI: 10.1021/bi9928546. View

16.

Dix T, Bollag G, Domanico P, Benkovic S . Phenylalanine hydroxylase: absolute configuration and source of oxygen of the 4a-hydroxytetrahydropterin species. Biochemistry. 1985; 24(12):2955-8. DOI: 10.1021/bi00333a022. View

17.

Tong J, Diorio A, Benoiton N . Formation of meta-tyrosine form L-phenylalanine by beef adrenal medulla. A new biosynthetic route to catecholamines. Biochem Biophys Res Commun. 1971; 44(1):229-36. DOI: 10.1016/s0006-291x(71)80183-3. View

18.

Wasinger E, Mitic N, Hedman B, Caradonna J, Solomon E, Hodgson K . X-ray absorption spectroscopic investigation of the resting ferrous and cosubstrate-bound active sites of phenylalanine hydroxylase. Biochemistry. 2002; 41(20):6211-7. DOI: 10.1021/bi0121510. View

19.

Gibbs B, Wojchowski D, Benkovic S . Expression of rat liver phenylalanine hydroxylase in insect cells and site-directed mutagenesis of putative non-heme iron-binding sites. J Biol Chem. 1993; 268(11):8046-52. View

20.

McKinney J, Teigen K, Froystein N, Salaun C, Knappskog P, Haavik J . Conformation of the substrate and pterin cofactor bound to human tryptophan hydroxylase. Important role of Phe313 in substrate specificity. Biochemistry. 2001; 40(51):15591-601. DOI: 10.1021/bi015722x. View