Release of free amino acids upon oxidation of peptides and proteins by hydroxyl radicals

Analytical and Bioanalytical Chemistry

Volumn 409, Issue 9, 2017, Pages 2411-2420

  Liu, Fobang ^a   Lai, Senchao ^b   Tong, Haijie ^a   Lakey, Pascale S J ^a   Shiraiwa, Manabu ^a,c   Weller, Michael G ^d   Pöschl, Ulrich ^a   Kampf, Christopher J ^a,e  

^a MAX PLANCK INSTITUTE FOR CHEMISTRY   (Germany)

^b SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d BAM FEDERAL INSTITUTE FOR MATERIALS RESEARCH AND TESTING   (Germany)

^e JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Amino acid analysis; HPLC MS; Hydroxyl radicals; Oxidation; Peptides; Proteins

Indexed keywords

AMINO ACIDS; COLUMN CHROMATOGRAPHY; FREE RADICALS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IRON COMPOUNDS; MAMMALS; MASS SPECTROMETRY; METAL IONS; PEPTIDES; PROTEINS;

AMINO ACID ANALYSIS; BOVINE SERUM ALBUMINS; DIODE ARRAY DETECTION; FLUORESCENCE DETECTION; HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY TANDEM MASS SPECTROMETRIES; HPLC-MS; HYDROXYL RADICALS; ORTHO-PHTHALALDEHYDE;

OXIDATION;

AMINO ACID; HYDROXYL RADICAL; PEPTIDE; PROTEIN; REACTIVE OXYGEN METABOLITE;

CHEMISTRY; OXIDATION REDUCTION REACTION;

AMINO ACIDS; HYDROXYL RADICAL; OXIDATION-REDUCTION; PEPTIDES; PROTEINS; REACTIVE OXYGEN SPECIES;

EID: 85009853933     PISSN: 16182642     EISSN: 16182650     Source Type: Journal    
DOI: 10.1007/s00216-017-0188-y     Document Type: Article

References (46)

1. Waris G, Ahsan H. Reactive oxygen species: role in the development of cancer and various chronic conditions. J Carcinog. 2006;5:14.
2. Valko M, Jomova K, Rhodes CJ, Kuča K, Musílek K. Redox-and non-redox-metal-induced formation of free radicals and their role in human disease. Arch Toxicol. 2016;90:1–37.
3. Oyinloye BE, Adenowo AF, Kappo AP. Reactive oxygen species, apoptosis, antimicrobial peptides and human inflammatory diseases. Pharmaceuticals. 2015;8:151–75.
4. Pöschl U, Shiraiwa M. Multiphase chemistry at the atmosphere–biosphere interface influencing climate and public health in the anthropocene. Chem Rev. 2015;115:4440–75.
5. Wang Y, Chen J, Ling M, López JA, Chung DW, Fu X. Hypochlorous acid generated by neutrophils inactivates ADAMTS13 an oxidative mechanism for regulating ADAMTS13 proteolytic activity during inflammation. J Biol Chem. 2015;290:1422–31.
6. Chen X, Mou Y, Ling J, Wang N, Wang X, Hu J. Cyclic dipeptides produced by fungus Eupenicillium brefeldianum HMP-F96 induced extracellular alkalinization and H2O2 production in tobacco cell suspensions. World J Microbiol Biotechnol. 2015;31:247–53.
7. Abu-Soud HM, Maitra D, Shaeib F, Khan SN, Byun J, Abdulhamid I, et al. Disruption of heme-peptide covalent cross-linking in mammalian peroxidases by hypochlorous acid. J Inorg Biochem. 2014;140:245–54.
8. Kocha T, Yamaguchi M, Ohtaki H, Fukuda T, Aoyagi T. Hydrogen peroxide-mediated degradation of protein: different oxidation modes of copper-and iron-dependent hydroxyl radicals on the degradation of albumin. BBA-Protein Struct M. 1997;1337:319–26.
9. Doan HQ, Davis AC, Francisco JS. Primary steps in the reaction of OH radicals with peptide systems: perspective from a study of model amides. J Phys Chem A. 2010;114:5342–57.
10. Apel K, Hirt H. Reactive oxygen species: metabolism, oxidative stress, and signal transduction. Annu Rev Plant Biol. 2004;55:373–99.
11. Xu G, Chance MR. Hydroxyl radical-mediated modification of proteins as probes for structural proteomics. Chem Rev. 2007;107:3514–43.
12. Watson C, Janik I, Zhuang T, Charvátová O, Woods RJ, Sharp JS. Pulsed electron beam water radiolysis for submicrosecond hydroxyl radical protein footprinting. Anal Chem. 2009;81:2496–505.
13. Stadtman E, Levine R. Free radical-mediated oxidation of free amino acids and amino acid residues in proteins. Amino Acids. 2003;25:207–18.
14. Davies MJ. Protein oxidation and peroxidation. Biochem J. 2016;473:805–25.
15. Štefanić I, Ljubić I, Bonifačić M, Sabljić A, Asmus K-D, Armstrong DA. A surprisingly complex aqueous chemistry of the simplest amino acid. A pulse radiolysis and theoretical study on H/D kinetic isotope effects in the reaction of glycine anions with hydroxyl radicals. Phys Chem Chem Phys. 2009;11:2256–67.
16. Stadtman ER. Protein oxidation and aging. Science. 1992;257:1220–4.
17. Cape J, Cornell S, Jickells T, Nemitz E. Organic nitrogen in the atmosphere—where does it come from? A review of sources and methods. Atmos Res. 2011;102:30–48.
18. McGregor KG, Anastasio C. Chemistry of fog waters in California’s Central Valley: 2. Photochemical transformations of amino acids and alkyl amines. Atmos Environ. 2001;35:1091–104.
19. Sharma VK, Rokita SE. Oxidation of amino acids, peptides, and proteins: kinetics and mechanism. John Wiley & Sons; 2012.
20. Stadtman ER. Protein oxidation and aging. Free Radic Res. 2006;40:1250–8.
21. Davies MJ. The oxidative environment and protein damage. BBA-Proteins Proteom. 1703;2005:93–109.
22. Rauk A, Armstrong DA. Influence of β-sheet structure on the susceptibility of proteins to backbone oxidative damage: preference for αc-centered radical formation at glycine residues of antiparallel β-sheets. J Am Chem Soc. 2000;122:4185–92.
23. Hawkins C, Davies M. EPR studies on the selectivity of hydroxyl radical attack on amino acids and peptides. J Chem Soc Perk Trans. 1998;2:2617–22.
24. Dufield DR, Wilson GS, Glass RS, Schöneich C. Selective site-specific Fenton oxidation of methionine in model peptides: evidence for a metal-bound oxidant. J Pharm Sci. 2004;93:1122–30.
25. Uehara H, Luo S, Aryal B, Levine RL, Rao VA. Distinct oxidative cleavage and modification of bovine [Cu–Zn]-SOD by an ascorbic acid/Cu (II) system: identification of novel copper binding site on SOD molecule. Free Radic Bio Med. 2016;94:161–73.
26. Zhou X, Mester C, Stemmer PM, Reid GE. Oxidation-induced conformational changes in calcineurin determined by covalent labeling and tandem mass spectrometry. Biochemistry-US. 2014;53(43):6754–65.
27. Morgan PE, Pattison DI, Hawkins CL, Davies MJ. Separation, detection, and quantification of hydroperoxides formed at side-chain and backbone sites on amino acids, peptides, and proteins. Free Radic Biol Med. 2008;45:1279–89.
28. Morgan PE, Pattison DI, Davies MJ. Quantification of hydroxyl radical-derived oxidation products in peptides containing glycine, alanine, valine, and proline. Free Radic Biol Med. 2012;52:328–39.
29. Guedes S, Vitorino R, Domingues R, Amado F, Domingues P. Oxidation of bovine serum albumin: identification of oxidation products and structural modifications. Rapid Commun Mass Spectrom. 2009;23:2307–15.
30. Marx G, Chevion M. Site-specific modification of albumin by free radicals. Reaction with copper(II) and ascorbate. Biochem J. 1986;236:397–400.
31. Catalano CE, Choe YS, de Montellano PO. Reactions of the protein radical in peroxide-treated myoglobin. Formation of a heme-protein cross-link. J Biol Chem. 1989;264:10534–41.
32. Lee SH, Kyung H, Yokota R, Goto T, Oe T. Hydroxyl radical-mediated novel modification of peptides: N-terminal cyclization through the formation of α-ketoamide. Chem Res Toxicol. 2014;28:59–70.
33. Schwarz EL, Roberts WL, Pasquali M. Analysis of plasma amino acids by HPLC with photodiode array and fluorescence detection. Clin Chim Acta. 2005;354:83–90.
34. Thiele B, Füllner K, Stein N, Oldiges M, Kuhn AJ, Hofmann D. Analysis of amino acids without derivatization in barley extracts by LC-MS-MS. Anal Bioanal Chem. 2008;391:2663–72.
35. Baron CP, Refsgaard HH, Skibsted LH, Andersen ML. Oxidation of bovine serum albumin initiated by the Fenton reaction–effect of EDTA, tert-butylhydroperoxide and tetrahydrofuran. Free Radic Res. 2006;40:409–17.
36. Oviedo C, Contreras D, Freer J, Rodriguez J. Fe(III)-EDTA complex abatement using a catechol driven Fenton reaction combined with a biological treatment. Environ Technol. 2004;25:801–7.
37. Henderson J, Ricker R, Bidlingmeyer B, Woodward C. Rapid, accurate, sensitive, and reproducible HPLC analysis of amino acids. Agilent Technologies. Technical Note 5980-1193E, J. R. Soc. Interface 9. 2000.
38. Gómez-Ariza J, Villegas-Portero M, Bernal-Daza V. Characterization and analysis of amino acids in orange juice by HPLC–MS/MS for authenticity assessment. Anal Chim Acta. 2005;540:221–30.
39. Buxton GV, Greenstock CL, Helman WP, Ross AB. Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (⋅OH/⋅O− in aqueous solution). J Phys Chem Ref Data. 1988;17:513–886.
40. Bachi A, Dalle-Donne I, Scaloni A. Redox proteomics: chemical principles, methodological approaches and biological/biomedical promises. Chem Rev. 2012;113:596–698.
41. Le Maux S, Nongonierma AB, Barre C, FitzGerald RJ. Enzymatic generation of whey protein hydrolysates under pH-controlled and non pH-controlled conditions: impact on physicochemical and bioactive properties. Food Chem. 2016;199:246–51.
42. Uchida K, Kato Y, Kawakishi S. A novel mechanism for oxidative cleavage of prolyl peptides induced by the hydroxyl radical. Biochem Biophys Res Commun. 1990;169:265–71.
43. Štefanić I, Bonifačić M, Asmus K-D, Armstrong DA. Absolute rate constants and yields of transients from hydroxyl radical and H atom attack on glycine and methyl-substituted glycine anions. J Phys Chem A. 2001;105:8681–90.
44. Hawkins CL, Davies MJ. Generation and propagation of radical reactions on proteins. BBA-Bioenergetics. 2001;1504:196–219.
45. Tong H, Arangio AM, Lakey PS, Berkemeier T, Liu F, Kampf CJ, et al. Hydroxyl radicals from secondary organic aerosol decomposition in water. Atmos Chem Phys. 2016;16:1761–71.
46. Arangio AM, Tong H, Socorro J, Pöschl U, Shiraiwa M. Quantification of environmentally persistent free radicals and reactive oxygen species in atmospheric aerosol particles. Atmos Chem Phys. 2016;16:13105–19.