Literature DB >> 24168553

Pulsed EPR study of amino acid and tetrahydropterin binding in a tyrosine hydroxylase nitric oxide complex: evidence for substrate rearrangements in the formation of the oxygen-reactive complex.

Matthew D Krzyaniak1, Bekir E Eser, Holly R Ellis, Paul F Fitzpatrick, John McCracken.   

Abstract

Tyrosine hydroxylase is a nonheme iron enzyme found in the nervous system that catalyzes the hydroxylation of tyrosine to form l-3,4-dihydroxyphenylalanine, the rate-limiting step in the biosynthesis of the catecholamine neurotransmitters. Catalysis requires the binding of three substrates: tyrosine, tetrahydrobiopterin, and molecular oxygen. We have used nitric oxide as an O₂ surrogate to poise Fe(II) at the catalytic site in an S = 3/2, {FeNO}⁷ form amenable to EPR spectroscopy. ²H-electron spin echo envelope modulation was then used to measure the distance and orientation of specifically deuterated substrate tyrosine and cofactor 6-methyltetrahydropterin with respect to the magnetic axes of the {FeNO}⁷ paramagnetic center. Our results show that the addition of tyrosine triggers a conformational change in the enzyme that reduces the distance from the {FeNO}⁷ center to the closest deuteron on 6,7-²H-6-methyltetrahydropterin from >5.9 Å to 4.4 ± 0.2 Å. Conversely, the addition of 6-methyltetrahydropterin to enzyme samples treated with 3,5-²H-tyrosine resulted in reorientation of the magnetic axes of the S = 3/2, {FeNO}⁷ center with respect to the deuterated substrate. Taken together, these results show that the coordination of both substrate and cofactor direct the coordination of NO to Fe(II) at the active site. Parallel studies of a quaternary complex of an uncoupled tyrosine hydroxylase variant, E332A, show no change in the hyperfine coupling to substrate tyrosine and cofactor 6-methyltetrahydropterin. Our results are discussed in the context of previous spectroscopic and X-ray crystallographic studies done on tyrosine hydroxylase and phenylalanine hydroxylase.

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Year:  2013        PMID: 24168553      PMCID: PMC3902855          DOI: 10.1021/bi4010914

Source DB:  PubMed          Journal:  Biochemistry        ISSN: 0006-2960            Impact factor:   3.162


  38 in total

Review 1.  Tetrahydropterin-dependent amino acid hydroxylases.

Authors:  P F Fitzpatrick
Journal:  Annu Rev Biochem       Date:  1999       Impact factor: 23.643

2.  Crystal structure of tyrosine hydroxylase at 2.3 A and its implications for inherited neurodegenerative diseases.

Authors:  K E Goodwill; C Sabatier; C Marks; R Raag; P F Fitzpatrick; R C Stevens
Journal:  Nat Struct Biol       Date:  1997-07

3.  EasySpin, a comprehensive software package for spectral simulation and analysis in EPR.

Authors:  Stefan Stoll; Arthur Schweiger
Journal:  J Magn Reson       Date:  2005-09-26       Impact factor: 2.229

4.  "NONOates" (1-substituted diazen-1-ium-1,2-diolates) as nitric oxide donors: convenient nitric oxide dosage forms.

Authors:  L K Keefer; R W Nims; K M Davies; D A Wink
Journal:  Methods Enzymol       Date:  1996       Impact factor: 1.600

5.  Regulation of phenylalanine hydroxylase: conformational changes upon phenylalanine binding detected by hydrogen/deuterium exchange and mass spectrometry.

Authors:  Jun Li; Lawrence J Dangott; Paul F Fitzpatrick
Journal:  Biochemistry       Date:  2010-04-20       Impact factor: 3.162

6.  2.0A resolution crystal structures of the ternary complexes of human phenylalanine hydroxylase catalytic domain with tetrahydrobiopterin and 3-(2-thienyl)-L-alanine or L-norleucine: substrate specificity and molecular motions related to substrate binding.

Authors:  Ole Andreas Andersen; Anne J Stokka; Torgeir Flatmark; Edward Hough
Journal:  J Mol Biol       Date:  2003-10-31       Impact factor: 5.469

7.  Spectroscopy and kinetics of wild-type and mutant tyrosine hydroxylase: mechanistic insight into O2 activation.

Authors:  Marina S Chow; Bekir E Eser; Samuel A Wilson; Keith O Hodgson; Britt Hedman; Paul F Fitzpatrick; Edward I Solomon
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

8.  EPR and Mössbauer studies of protocatechuate 4,5-dioxygenase. Characterization of a new Fe2+ environment.

Authors:  D M Arciero; J D Lipscomb; B H Huynh; T A Kent; E Münck
Journal:  J Biol Chem       Date:  1983-12-25       Impact factor: 5.157

9.  Thiolate ligation of the active site Fe2+ of isopenicillin N synthase derives from substrate rather than endogenous cysteine: spectroscopic studies of site-specific Cys----Ser mutated enzymes.

Authors:  A M Orville; V J Chen; A Kriauciunas; M R Harpel; B G Fox; E Münck; J D Lipscomb
Journal:  Biochemistry       Date:  1992-05-19       Impact factor: 3.162

10.  VTVH-MCD and DFT studies of thiolate bonding to [FeNO]7/[FeO2]8 complexes of isopenicillin N synthase: substrate determination of oxidase versus oxygenase activity in nonheme Fe enzymes.

Authors:  Christina D Brown; Michael L Neidig; Matthew B Neibergall; John D Lipscomb; Edward I Solomon
Journal:  J Am Chem Soc       Date:  2007-05-17       Impact factor: 15.419

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  8 in total

Review 1.  Dioxygen activation by nonheme iron enzymes with the 2-His-1-carboxylate facial triad that generate high-valent oxoiron oxidants.

Authors:  Subhasree Kal; Lawrence Que
Journal:  J Biol Inorg Chem       Date:  2017-01-10       Impact factor: 3.358

Review 2.  Spectroscopic analyses of 2-oxoglutarate-dependent oxygenases: TauD as a case study.

Authors:  Denis A Proshlyakov; John McCracken; Robert P Hausinger
Journal:  J Biol Inorg Chem       Date:  2016-11-03       Impact factor: 3.358

3.  1H-HYSCORE Reveals Structural Details at the Fe(II) Active Site of Taurine:2-Oxoglutarate Dioxygenase.

Authors:  John McCracken; Thomas M Casey; Robert P Hausinger
Journal:  Appl Magn Reson       Date:  2020-10-28       Impact factor: 0.974

Review 4.  Carbon-fluorine bond cleavage mediated by metalloenzymes.

Authors:  Yifan Wang; Aimin Liu
Journal:  Chem Soc Rev       Date:  2020-06-08       Impact factor: 54.564

5.  Characterization of unstable products of flavin- and pterin-dependent enzymes by continuous-flow mass spectrometry.

Authors:  Kenneth M Roberts; José R Tormos; Paul F Fitzpatrick
Journal:  Biochemistry       Date:  2014-04-18       Impact factor: 3.162

6.  Activation of phenylalanine hydroxylase by phenylalanine does not require binding in the active site.

Authors:  Kenneth M Roberts; Crystal A Khan; Cynthia S Hinck; Paul F Fitzpatrick
Journal:  Biochemistry       Date:  2014-12-02       Impact factor: 3.162

7.  Evaluation on monoamine neurotransmitters changes in depression rats given with sertraline, meloxicam or/and caffeic acid.

Authors:  Dan Huang; Lu Zhang; Jun-Qing Yang; Ying Luo; Ting Cui; Ting-Ting Du; Xin-Hui Jiang
Journal:  Genes Dis       Date:  2018-06-15

8.  OvoAMtht from Methyloversatilis thermotolerans ovothiol biosynthesis is a bifunction enzyme: thiol oxygenase and sulfoxide synthase activities.

Authors:  Ronghai Cheng; Andrew C Weitz; Jared Paris; Yijie Tang; Jingyu Zhang; Heng Song; Nathchar Naowarojna; Kelin Li; Lu Qiao; Juan Lopez; Mark W Grinstaff; Lixin Zhang; Yisong Guo; Sean Elliott; Pinghua Liu
Journal:  Chem Sci       Date:  2022-03-02       Impact factor: 9.825

  8 in total

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