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Literature DB >> 22210190

Redox properties of tyrosine and related molecules.

Jeffrey J Warren¹, Jay R Winkler, Harry B Gray.

Abstract

Redox reactions of tyrosine play key roles in many biological processes, including water oxidation and DNA synthesis. We first review the redox properties of tyrosine (and other phenols) in small molecules and related polypeptides, then report work on (H20)/(Y48)-modified Pseudomonas aeruginosa azurin. The crystal structure of this protein (1.18Å resolution) shows that H20 is strongly hydrogen bonded to Y48 (2.7-2.8Å tyrosine-O to histidine-N distance). A firm conclusion is that proper tuning of the tyrosine potential by a proton-accepting base is critical for biological redox functions. Copyright Â

Entities: Chemical Disease Gene Species

Mesh：

Substances：
Azurin
Tyrosine
Histidine

Year: 2011 PMID： 22210190 PMCID： PMC3298607 DOI： 10.1016/j.febslet.2011.12.014

Source DB: PubMed Journal: FEBS Lett ISSN： 0014-5793 Impact factor: 4.124

45 in total

1. Moving a phenol hydroxyl group from the surface to the interior of a protein: effects on the phenol potential and pK(A).

Authors: Sam Hay; Kristina Westerlund; Cecilia Tommos
Journal: Biochemistry Date: 2005-09-06 Impact factor: 3.162

2. Concerted proton-electron transfer in the oxidation of hydrogen-bonded phenols.

Authors: Ian J Rhile; Todd F Markle; Hirotaka Nagao; Antonio G DiPasquale; Oanh P Lam; Mark A Lockwood; Katrina Rotter; James M Mayer
Journal: J Am Chem Soc Date: 2006-05-10 Impact factor: 15.419

3. The role of free energy change in coupled electron-proton transfer.

Authors: Christine J Fecenko; H Holden Thorp; Thomas J Meyer
Journal: J Am Chem Soc Date: 2007-11-14 Impact factor: 15.419

4. Electron transfer in peptides with cysteine and methionine as relay amino acids.

Authors: Min Wang; Jian Gao; Pavel Müller; Bernd Giese
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

5. Influence of amino acid side chains on long-distance electron transfer in peptides: electron hopping via "stepping stones".

Authors: Meike Cordes; Angnieszka Köttgen; Christian Jasper; Olivier Jacques; Hassen Boudebous; Bernd Giese
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

6. Intrinsic reactivity and driving force dependence in concerted proton-electron transfers to water illustrated by phenol oxidation.

Authors: Julien Bonin; Cyrille Costentin; Cyril Louault; Marc Robert; Mathilde Routier; Jean-Michel Savéant
Journal: Proc Natl Acad Sci U S A Date: 2010-02-05 Impact factor: 11.205

7. Direct tyrosine oxidation using the MLCT excited states of rhenium polypyridyl complexes.

Authors: Steven Y Reece; Daniel G Nocera
Journal: J Am Chem Soc Date: 2005-07-06 Impact factor: 15.419

8. Catalysis of electron transfer during activation of O2 by the flavoprotein glucose oxidase.

Authors: Justine P Roth; Judith P Klinman
Journal: Proc Natl Acad Sci U S A Date: 2002-12-27 Impact factor: 11.205

Review 9. Prostaglandin H synthase: resolved and unresolved mechanistic issues.

Authors: Ah-Lim Tsai; Richard J Kulmacz
Journal: Arch Biochem Biophys Date: 2009-09-01 Impact factor: 4.013

10. Electrochemical and structural properties of a protein system designed to generate tyrosine Pourbaix diagrams.

Authors: Melissa C Martínez-Rivera; Bruce W Berry; Kathleen G Valentine; Kristina Westerlund; Sam Hay; Cecilia Tommos
Journal: J Am Chem Soc Date: 2011-10-19 Impact factor: 15.419

33 in total

1. Photophysics of a protein-bound derivative of malachite green that sensitizes the production of singlet oxygen.

Authors: Lea Dichmann; Mikkel Bregnhøj; Han Liu; Michael Westberg; Thomas B Poulsen; Michael Etzerodt; Peter R Ogilby
Journal: Photochem Photobiol Sci Date: 2021-03-15 Impact factor: 3.982

2. Constraints on the Radical Cation Center of Cytochrome c Peroxidase for Electron Transfer from Cytochrome c.

Authors: Thomas M Payne; Estella F Yee; Boris Dzikovski; Brian R Crane
Journal: Biochemistry Date: 2016-08-17 Impact factor: 3.162

3. Stopped-Flow Studies of the Reduction of the Copper Centers Suggest a Bifurcated Electron Transfer Pathway in Peptidylglycine Monooxygenase.

Authors: Shefali Chauhan; Parisa Hosseinzadeh; Yi Lu; Ninian J Blackburn
Journal: Biochemistry Date: 2016-03-23 Impact factor: 3.162

Redox properties of tyrosine and related molecules.

1. Moving a phenol hydroxyl group from the surface to the interior of a protein: effects on the phenol potential and pK(A).

2. Concerted proton-electron transfer in the oxidation of hydrogen-bonded phenols.

3. The role of free energy change in coupled electron-proton transfer.

4. Electron transfer in peptides with cysteine and methionine as relay amino acids.

5. Influence of amino acid side chains on long-distance electron transfer in peptides: electron hopping via "stepping stones".

6. Intrinsic reactivity and driving force dependence in concerted proton-electron transfers to water illustrated by phenol oxidation.

7. Direct tyrosine oxidation using the MLCT excited states of rhenium polypyridyl complexes.

8. Catalysis of electron transfer during activation of O2 by the flavoprotein glucose oxidase.

Review 9. Prostaglandin H synthase: resolved and unresolved mechanistic issues.

10. Electrochemical and structural properties of a protein system designed to generate tyrosine Pourbaix diagrams.

1. Photophysics of a protein-bound derivative of malachite green that sensitizes the production of singlet oxygen.

2. Constraints on the Radical Cation Center of Cytochrome c Peroxidase for Electron Transfer from Cytochrome c.

3. Stopped-Flow Studies of the Reduction of the Copper Centers Suggest a Bifurcated Electron Transfer Pathway in Peptidylglycine Monooxygenase.

4. Redox Signaling through DNA.

5. Active-Site Environmental Factors Customize the Photophysics of Photoenzymatic Old Yellow Enzymes.

6. Characterization of the DNA-Mediated Oxidation of Dps, A Bacterial Ferritin.

7. Electron hopping through proteins.

8. Side-chain thioamides as fluorescence quenching probes.

9. Iron(IV)hydroxide pK(a) and the role of thiolate ligation in C-H bond activation by cytochrome P450.

10. Reversible phenol oxidation and reduction in the structurally well-defined 2-Mercaptophenol-α₃C protein.