Release of free amino acids upon oxidation of peptides and proteins by hydroxyl radicals
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Fobang Liu
- Senchao Lai
- Haijie Tong
- Pascale SJ Lakey
- Manabu Shiraiwa
- Michael G Weller
- Ulrich Poeschl
- Christopher J Kampf
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000396781700016&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1007/s00216-017-0188-y
- eISSN
- 1618-2650
- Externe Identifier
- Clarivate Analytics Document Solution ID: EO6DJ
- PubMed Identifier: 28108753
- ISSN
- 1618-2642
- Ausgabe der Veröffentlichung
- 9
- Zeitschrift
- ANALYTICAL AND BIOANALYTICAL CHEMISTRY
- Schlüsselwörter
- Peptides
- Proteins
- Oxidation
- Hydroxyl radicals
- HPLC-MS
- Amino acid analysis
- Paginierung
- 2411 - 2420
- Datum der Veröffentlichung
- 2017
- Status
- Published
- Titel
- Release of free amino acids upon oxidation of peptides and proteins by hydroxyl radicals
- Sub types
- Article
- Ausgabe der Zeitschrift
- 409
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Autoren
- Fobang Liu
- Senchao Lai
- Haijie Tong
- Pascale SJ Lakey
- Manabu Shiraiwa
- Michael G Weller
- Ulrich Pöschl
- Christopher J Kampf
- DOI
- 10.1007/s00216-017-0188-y
- eISSN
- 1618-2650
- ISSN
- 1618-2642
- Ausgabe der Veröffentlichung
- 9
- Zeitschrift
- Analytical and Bioanalytical Chemistry
- Sprache
- en
- Online publication date
- 2017
- Paginierung
- 2411 - 2420
- Datum der Veröffentlichung
- 2017
- Status
- Published
- Herausgeber
- Springer Science and Business Media LLC
- Herausgeber URL
- http://dx.doi.org/10.1007/s00216-017-0188-y
- Datum der Datenerfassung
- 2022
- Titel
- Release of free amino acids upon oxidation of peptides and proteins by hydroxyl radicals
- Ausgabe der Zeitschrift
- 409
Datenquelle: Crossref
- Abstract
- Hydroxyl radical-induced oxidation of proteins and peptides can lead to the cleavage of the peptide, leading to a release of fragments. Here, we used high-performance liquid chromatography tandem mass spectrometry (HPLC-MS/MS) and pre-column online ortho-phthalaldehyde (OPA) derivatization-based amino acid analysis by HPLC with diode array detection and fluorescence detection to identify and quantify free amino acids released upon oxidation of proteins and peptides by hydroxyl radicals. Bovine serum albumin (BSA), ovalbumin (OVA) as model proteins, and synthetic tripeptides (comprised of varying compositions of the amino acids Gly, Ala, Ser, and Met) were used for reactions with hydroxyl radicals, which were generated by the Fenton reaction of iron ions and hydrogen peroxide. The molar yields of free glycine, aspartic acid, asparagine, and alanine per peptide or protein varied between 4 and 55%. For protein oxidation reactions, the molar yields of Gly (∼32-55% for BSA, ∼10-21% for OVA) were substantially higher than those for the other identified amino acids (∼5-12% for BSA, ∼4-6% for OVA). Upon oxidation of tripeptides with Gly in C-terminal, mid-chain, or N-terminal positions, Gly was preferentially released when it was located at the C-terminal site. Overall, we observe evidence for a site-selective formation of free amino acids in the OH radical-induced oxidation of peptides and proteins, which may be due to a reaction pathway involving nitrogen-centered radicals.
- Addresses
- Multiphase Chemistry Department, Max Planck Institute for Chemistry, Hahn-Meitner-Weg 1, 55128, Mainz, Germany.
- Autoren
- Fobang Liu
- Senchao Lai
- Haijie Tong
- Pascale SJ Lakey
- Manabu Shiraiwa
- Michael G Weller
- Ulrich Pöschl
- Christopher J Kampf
- DOI
- 10.1007/s00216-017-0188-y
- eISSN
- 1618-2650
- Externe Identifier
- PubMed Identifier: 28108753
- PubMed Central ID: PMC5352754
- Funding acknowledgements
- Deutsche Forschungsgemeinschaft: KA4008/1-2
- China Scholarship Council:
- Max Planck Graduate Center mit der Johannes Gutenberg-Universität Mainz:
- Open access
- true
- ISSN
- 1618-2642
- Ausgabe der Veröffentlichung
- 9
- Zeitschrift
- Analytical and bioanalytical chemistry
- Schlüsselwörter
- Hydroxyl Radical
- Reactive Oxygen Species
- Amino Acids
- Peptides
- Proteins
- Oxidation-Reduction
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2017
- Open access status
- Open Access
- Paginierung
- 2411 - 2420
- Datum der Veröffentlichung
- 2017
- Status
- Published
- Publisher licence
- CC BY
- Datum der Datenerfassung
- 2017
- Titel
- Release of free amino acids upon oxidation of peptides and proteins by hydroxyl radicals.
- Sub types
- research-article
- Journal Article
- Ausgabe der Zeitschrift
- 409
Files
https://link.springer.com/content/pdf/10.1007%2Fs00216-017-0188-y.pdf https://europepmc.org/articles/PMC5352754?pdf=render
Datenquelle: Europe PubMed Central
- Abstract
- Hydroxyl radical-induced oxidation of proteins and peptides can lead to the cleavage of the peptide, leading to a release of fragments. Here, we used high-performance liquid chromatography tandem mass spectrometry (HPLC-MS/MS) and pre-column online ortho-phthalaldehyde (OPA) derivatization-based amino acid analysis by HPLC with diode array detection and fluorescence detection to identify and quantify free amino acids released upon oxidation of proteins and peptides by hydroxyl radicals. Bovine serum albumin (BSA), ovalbumin (OVA) as model proteins, and synthetic tripeptides (comprised of varying compositions of the amino acids Gly, Ala, Ser, and Met) were used for reactions with hydroxyl radicals, which were generated by the Fenton reaction of iron ions and hydrogen peroxide. The molar yields of free glycine, aspartic acid, asparagine, and alanine per peptide or protein varied between 4 and 55%. For protein oxidation reactions, the molar yields of Gly (∼32-55% for BSA, ∼10-21% for OVA) were substantially higher than those for the other identified amino acids (∼5-12% for BSA, ∼4-6% for OVA). Upon oxidation of tripeptides with Gly in C-terminal, mid-chain, or N-terminal positions, Gly was preferentially released when it was located at the C-terminal site. Overall, we observe evidence for a site-selective formation of free amino acids in the OH radical-induced oxidation of peptides and proteins, which may be due to a reaction pathway involving nitrogen-centered radicals.
- Date of acceptance
- 2017
- Autoren
- Fobang Liu
- Senchao Lai
- Haijie Tong
- Pascale SJ Lakey
- Manabu Shiraiwa
- Michael G Weller
- Ulrich Pöschl
- Christopher J Kampf
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/28108753
- DOI
- 10.1007/s00216-017-0188-y
- eISSN
- 1618-2650
- Externe Identifier
- PubMed Central ID: PMC5352754
- Ausgabe der Veröffentlichung
- 9
- Zeitschrift
- Anal Bioanal Chem
- Schlüsselwörter
- Amino acid analysis
- HPLC-MS
- Hydroxyl radicals
- Oxidation
- Peptides
- Proteins
- Amino Acids
- Hydroxyl Radical
- Oxidation-Reduction
- Peptides
- Proteins
- Reactive Oxygen Species
- Sprache
- eng
- Country
- Germany
- Paginierung
- 2411 - 2420
- PII
- 10.1007/s00216-017-0188-y
- Datum der Veröffentlichung
- 2017
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2018
- Titel
- Release of free amino acids upon oxidation of peptides and proteins by hydroxyl radicals.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 409
Datenquelle: PubMed
- Beziehungen:
- Eigentum von