Electrospray ionization mass spectrometry applied to study the radical acetylation of amino acids, peptides and proteins
Autor(a) principal: | |
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Data de Publicação: | 2013 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Journal of the Brazilian Chemical Society (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013001200012 |
Resumo: | Recently, our group proposed a process that generated acetyl radicals in a reaction medium buffered with a diacetyl/peroxynitrite system. Diacetyl is a flavoring agent in food, cigarettes and drinks. Peroxynitrite is found in mitochondria, and in certain conditions, such as an infection in humans, its concentration is augmented significantly. In biological systems, radical compounds can easily modify the structure and activity of nucleic acids, proteins and other biomolecules, causing significant oxidative stress. Based on paramagnetic resonance and mass spectrometry data, this work discusses products that prove acetyl radicals are produced and are able to form stable covalent bonds with amino acid (acetylated products), peptide and protein adducts. These materials were separated and detected by capillary electrophoresis coupled with tandem mass spectrometry or offline mass spectrometry. The reaction medium contained a 1:2 mixture of diacetyl and peroxynitrite dissolved in 200 mmol L-1 of pH 7.2 sodium phosphate buffer. These experiments also reveal the double acetylation of lysine, demonstrating the high reactivity of these compounds when in contact with nitrogen-containing biomolecules readily found in biological systems. These structural changes might be an epigenetic source of post-translational protein modification. |
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Electrospray ionization mass spectrometry applied to study the radical acetylation of amino acids, peptides and proteinsacetylation of biomoleculesacetyl radicalperoxynitritediacetylmass spectrometryCE/ESI-MS/MSRecently, our group proposed a process that generated acetyl radicals in a reaction medium buffered with a diacetyl/peroxynitrite system. Diacetyl is a flavoring agent in food, cigarettes and drinks. Peroxynitrite is found in mitochondria, and in certain conditions, such as an infection in humans, its concentration is augmented significantly. In biological systems, radical compounds can easily modify the structure and activity of nucleic acids, proteins and other biomolecules, causing significant oxidative stress. Based on paramagnetic resonance and mass spectrometry data, this work discusses products that prove acetyl radicals are produced and are able to form stable covalent bonds with amino acid (acetylated products), peptide and protein adducts. These materials were separated and detected by capillary electrophoresis coupled with tandem mass spectrometry or offline mass spectrometry. The reaction medium contained a 1:2 mixture of diacetyl and peroxynitrite dissolved in 200 mmol L-1 of pH 7.2 sodium phosphate buffer. These experiments also reveal the double acetylation of lysine, demonstrating the high reactivity of these compounds when in contact with nitrogen-containing biomolecules readily found in biological systems. These structural changes might be an epigenetic source of post-translational protein modification.Sociedade Brasileira de Química2013-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013001200012Journal of the Brazilian Chemical Society v.24 n.12 2013reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20130248info:eu-repo/semantics/openAccessAlves,Atecla N. L.Jedlicka,Leticia D. L.Massari,JúlioJuliano,Maria A.Bechara,Etelvino J. H.Assunção,Nilson A.eng2013-12-09T00:00:00Zoai:scielo:S0103-50532013001200012Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2013-12-09T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Electrospray ionization mass spectrometry applied to study the radical acetylation of amino acids, peptides and proteins |
title |
Electrospray ionization mass spectrometry applied to study the radical acetylation of amino acids, peptides and proteins |
spellingShingle |
Electrospray ionization mass spectrometry applied to study the radical acetylation of amino acids, peptides and proteins Alves,Atecla N. L. acetylation of biomolecules acetyl radical peroxynitrite diacetyl mass spectrometry CE/ESI-MS/MS |
title_short |
Electrospray ionization mass spectrometry applied to study the radical acetylation of amino acids, peptides and proteins |
title_full |
Electrospray ionization mass spectrometry applied to study the radical acetylation of amino acids, peptides and proteins |
title_fullStr |
Electrospray ionization mass spectrometry applied to study the radical acetylation of amino acids, peptides and proteins |
title_full_unstemmed |
Electrospray ionization mass spectrometry applied to study the radical acetylation of amino acids, peptides and proteins |
title_sort |
Electrospray ionization mass spectrometry applied to study the radical acetylation of amino acids, peptides and proteins |
author |
Alves,Atecla N. L. |
author_facet |
Alves,Atecla N. L. Jedlicka,Leticia D. L. Massari,Júlio Juliano,Maria A. Bechara,Etelvino J. H. Assunção,Nilson A. |
author_role |
author |
author2 |
Jedlicka,Leticia D. L. Massari,Júlio Juliano,Maria A. Bechara,Etelvino J. H. Assunção,Nilson A. |
author2_role |
author author author author author |
dc.contributor.author.fl_str_mv |
Alves,Atecla N. L. Jedlicka,Leticia D. L. Massari,Júlio Juliano,Maria A. Bechara,Etelvino J. H. Assunção,Nilson A. |
dc.subject.por.fl_str_mv |
acetylation of biomolecules acetyl radical peroxynitrite diacetyl mass spectrometry CE/ESI-MS/MS |
topic |
acetylation of biomolecules acetyl radical peroxynitrite diacetyl mass spectrometry CE/ESI-MS/MS |
description |
Recently, our group proposed a process that generated acetyl radicals in a reaction medium buffered with a diacetyl/peroxynitrite system. Diacetyl is a flavoring agent in food, cigarettes and drinks. Peroxynitrite is found in mitochondria, and in certain conditions, such as an infection in humans, its concentration is augmented significantly. In biological systems, radical compounds can easily modify the structure and activity of nucleic acids, proteins and other biomolecules, causing significant oxidative stress. Based on paramagnetic resonance and mass spectrometry data, this work discusses products that prove acetyl radicals are produced and are able to form stable covalent bonds with amino acid (acetylated products), peptide and protein adducts. These materials were separated and detected by capillary electrophoresis coupled with tandem mass spectrometry or offline mass spectrometry. The reaction medium contained a 1:2 mixture of diacetyl and peroxynitrite dissolved in 200 mmol L-1 of pH 7.2 sodium phosphate buffer. These experiments also reveal the double acetylation of lysine, demonstrating the high reactivity of these compounds when in contact with nitrogen-containing biomolecules readily found in biological systems. These structural changes might be an epigenetic source of post-translational protein modification. |
publishDate |
2013 |
dc.date.none.fl_str_mv |
2013-12-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013001200012 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013001200012 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.5935/0103-5053.20130248 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Journal of the Brazilian Chemical Society v.24 n.12 2013 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Journal of the Brazilian Chemical Society (Online) |
collection |
Journal of the Brazilian Chemical Society (Online) |
repository.name.fl_str_mv |
Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
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1750318175356977152 |