The role of acid–base equilibria in formal hydrogen transfer reactions: tryptophan radical repair by uric acid as a paradigmatic case

Literature Information

Publication Date 2017-05-16
DOI 10.1039/C7CP01557G
Impact Factor 3.676
Authors

Leonardo Muñoz-Rugeles, Annia Galano, Juan Raúl Alvarez-Idaboy


View Original

Abstract

The results presented in this work demonstrate the high complexity of chemical reactions involving species with multiple acid–base equilibria. For the case study investigated here, it was necessary to consider two radical species for tryptophan (Trp(−H)˙ and Trp˙+) and three fractions for uric acid (H3Ur, H2Ur− and HUr2−) in order to properly reproduce the experimental results. At pH = 7.4, two main reaction mechanisms were identified: proton–electron sequential transfer (PEST) and sequential proton gain-electron transfer (SPGET). Combined, they account for more than 99% of the overall reaction, despite the fact that they involve minor species, i.e., H3Ur and Trp˙+, respectively. The excellent agreement between the calculated overall rate constant and the experimental value seems to support this proposal. In addition, if only the dominant species at pH = 7.4 (H2Ur− and Trp(−H)˙) were considered, there would be a large discrepancy with the experimental value (about 4 orders of magnitude), which also supports the finding that the key species in this case are not the most abundant ones. The influence of the pH on the kinetics of the investigated reaction was explored. It was found that the maximum repairing ability of uric acid does not occur at physiological pH, but at a more acidic pH (pH = 5.0).

Related Literature

Surface plasmon resonance imaging of limited glycoprotein samples

Yi Chen, Mingdi Yan

2008-07-30 Paper

DOI: 10.1039/B804235G

Back cover

Front/Back Matter

DOI: 10.1039/B807518M

Genetic, genomic and physiological state studies on single-needle bio-electrosprayed human cells

Richard P. Hall, Caroline M. Ogilvie, Emma Aarons, Suwan N. Jayasinghe

2008-07-02 Communication

DOI: 10.1039/B806901H

Identification of Pseudomonas aeruginosa using functional magnetic nanoparticle-based affinity capture combined with MALDI MS analysis

Jr-Chi Liu, Wei-Jen Chen, Chen-Wei Li, Kwok-Kong Tony Mong, Pei-Jane Tsai, Te-Lung Tsai, Yuan C. Lee, Yu-Chie Chen

2009-07-24 Paper

DOI: 10.1039/B908069D

Discrimination between drug-resistant and non-resistant human melanoma cell lines by FTIR spectroscopy

A. Zwielly, G. Brkic, S. Mordechai

2008-10-24 Paper

DOI: 10.1039/B805223A

Multi-analyte sensing: a chemometrics approach to understanding the merits of electrode arrays versus single electrodes

Diako Ebrahimi, Edith Chow, Justin J. Gooding, David B. Hibbert

2008-06-19 Paper

DOI: 10.1039/B804811H

Multiple sized europium(III) chelate-dyed polystyrene particles as donors in FRET – an application for sensitive protein quantification utilizing competitive adsorption

Antti Valanne, Jouko Peltonen, Tero Soukka, Pekka Hänninen, Harri Härmä

2009-03-02 Paper

DOI: 10.1039/B821210D

Electrochemical studies on the oxidation of guanine and adenine at cyclodextrin modified electrodes

Abdolkarim Abbaspour, Abolhassan Noori

2008-09-02 Paper

DOI: 10.1039/B806920D

You might also like

Compound Q&A

Are there alternatives to 1-(4-Chlorophenyl)-N-hydroxymethanimine (CAS: 3848-36-0) in synthesis?

When considering alternatives to 1-(4-Chlorophenyl)-N-hydroxymethanimine (CAS: 3...

3848-36-01-(4-Chlorophenyl)-N...
Compound Q&A

How is 3-(4-Bromophenyl)-5-(2-fluorophenyl)-1,2,4-oxadiazole (CAS: 419553-16-5) typically synthesized?

3-(4-Bromophenyl)-5-(2-fluorophenyl)-1,2,4-oxadiazole is synthesized through a m...

419553-16-53-(4-Bromophenyl)-5-...
Compound Q&A

How is 5-Chloro-2-(4-chlorophenyl)-4-methyl-6-[3-(1-piperidinyl)propoxy]pyrimidine (CAS: 1639220-19-1) typically synthesized?

5-Chloro-2-(4-chlorophenyl)-4-methyl-6-[3-(1-piperidinyl)propoxy]pyrimidine (CAS...

1639220-19-15-Chloro-2-(4-chloro...
Compound Q&A

What industries use 2-Chloro-4-(difluoromethoxy)pyridine (CAS: 1206978-15-5)?

2-Chloro-4-(difluoromethoxy)pyridine is used in the pharmaceutical industry for ...

1206978-15-52-Chloro-4-(difluoro...
Compound Q&A

What regulatory guidelines apply to 3-Chloro-6-methylpyridazine (CAS: 1121-79-5)?

3-Chloro-6-methylpyridazine (CAS: 1121-79-5) is classified under the Globally Ha...

1121-79-53-Chloro-6-methylpyr...
Compound Q&A

Are there alternatives to Methyl 4,5-dimethyl-2-nitrobenzoate in synthesis?

Several alternatives can be used in the synthesis of Methyl 4,5-dimethyl-2-nitro...

90922-74-0Methyl 4,5-dimethyl-...
Compound Q&A

Are there alternatives to (2E,2'E)-3,3'-(1,4-Phenylene)bisacrylaldehyde in synthesis?

Alternatives to (2E,2'E)-3,3'-(1,4-Phenylene)bisacrylaldehyde include other acry...

63405-68-5(2E,2'E)-3,3'-(1,4-P...
Compound Q&A

What is 3-Amino-5-chloropyridin-2-ol hydrochloride (CAS: 1261906-29-9)?

3-Amino-5-chloropyridin-2-ol hydrochloride is an organic compound with the CAS n...

1261906-29-93-Amino-5-chloropyri...
Compound Q&A

What precautions should be taken when handling 6,7-Difluoro-2,3-dihydro-4H-chromen-4-one (CAS: 1092349-93-3)?

When handling 6,7-Difluoro-2,3-dihydro-4H-chromen-4-one, it is essential to wear...

1092349-93-36,7-Difluoro-2,3-dih...

Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.