Characterization of Reaction Products Formed in a Model Reaction between Pentanal and Lysine-Containing Oligopeptides
Aldehydes formed as a result of lipid oxidation form fluorophores after binding to proteins. The structure of the fluorophores formed by reaction between saturated aldehydes and lysine has not yet been identified. The reaction products formed in the reaction between pentanal and oligopeptides were s...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2006-08, Vol.54 (17), p.6367-6373 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Dalsgaard, Trine K Nielsen, Jacob H Larsen, Lotte B |
| description | Aldehydes formed as a result of lipid oxidation form fluorophores after binding to proteins. The structure of the fluorophores formed by reaction between saturated aldehydes and lysine has not yet been identified. The reaction products formed in the reaction between pentanal and oligopeptides were studied by fluorescence spectroscopy and mass spectrometry. The emission spectra showed an increase in fluorescence intensity with incubation time, and the rates were linear with the concentration of pentanal. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry analyses of the reaction products suggested a molar relation for peptide:pentanal of 1:4. Further tandem mass spectrometry analysis of one of the modified peptides (Pro-Thr-His-Ile-Lys-Trp-Gly-Asp) strongly suggested binding of one pentanal molecule to the amino terminal proline and three pentanal molecules bound to the lysine residue. The latter species is suggested to be the actual fluorophore, through the formation of conjugated double bonds, and a possible reaction pathway through a combination of aldol condensation of pentanal and Schiff base formation with the lysine is suggested. Keywords: Carbonyl modifications; Schiff base formation; aldol condensation; peptides; fluorescence spectroscopy; MALDI TOF MS-MS; fluorophore; lipid oxidation |
| doi_str_mv | 10.1021/jf060003g |
| format | Article |
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The structure of the fluorophores formed by reaction between saturated aldehydes and lysine has not yet been identified. The reaction products formed in the reaction between pentanal and oligopeptides were studied by fluorescence spectroscopy and mass spectrometry. The emission spectra showed an increase in fluorescence intensity with incubation time, and the rates were linear with the concentration of pentanal. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry analyses of the reaction products suggested a molar relation for peptide:pentanal of 1:4. Further tandem mass spectrometry analysis of one of the modified peptides (Pro-Thr-His-Ile-Lys-Trp-Gly-Asp) strongly suggested binding of one pentanal molecule to the amino terminal proline and three pentanal molecules bound to the lysine residue. The latter species is suggested to be the actual fluorophore, through the formation of conjugated double bonds, and a possible reaction pathway through a combination of aldol condensation of pentanal and Schiff base formation with the lysine is suggested. Keywords: Carbonyl modifications; Schiff base formation; aldol condensation; peptides; fluorescence spectroscopy; MALDI TOF MS-MS; fluorophore; lipid oxidation</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf060003g</identifier><identifier>PMID: 16910732</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>aldehydes ; Aldehydes - chemistry ; Amino Acid Sequence ; Biological and medical sciences ; chemical reactions ; fluorescence emission spectroscopy ; fluorophores ; food chemistry ; Food industries ; Fundamental and applied biological sciences. Psychology ; gas chromatography ; lysine ; Lysine - analysis ; Lysine - chemistry ; Mass Spectrometry ; oligopeptides ; Oligopeptides - chemistry ; pentanal ; reaction mechanisms ; reaction products ; Schiff bases ; Spectrometry, Fluorescence ; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</subject><ispartof>Journal of agricultural and food chemistry, 2006-08, Vol.54 (17), p.6367-6373</ispartof><rights>Copyright © 2006 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a405t-c686f195dfcf6759ae9f64346aa01d970ef7803c8934bed2e0c6ecf406de66193</citedby><cites>FETCH-LOGICAL-a405t-c686f195dfcf6759ae9f64346aa01d970ef7803c8934bed2e0c6ecf406de66193</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf060003g$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf060003g$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18045893$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16910732$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dalsgaard, Trine K</creatorcontrib><creatorcontrib>Nielsen, Jacob H</creatorcontrib><creatorcontrib>Larsen, Lotte B</creatorcontrib><title>Characterization of Reaction Products Formed in a Model Reaction between Pentanal and Lysine-Containing Oligopeptides</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Aldehydes formed as a result of lipid oxidation form fluorophores after binding to proteins. The structure of the fluorophores formed by reaction between saturated aldehydes and lysine has not yet been identified. The reaction products formed in the reaction between pentanal and oligopeptides were studied by fluorescence spectroscopy and mass spectrometry. The emission spectra showed an increase in fluorescence intensity with incubation time, and the rates were linear with the concentration of pentanal. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry analyses of the reaction products suggested a molar relation for peptide:pentanal of 1:4. Further tandem mass spectrometry analysis of one of the modified peptides (Pro-Thr-His-Ile-Lys-Trp-Gly-Asp) strongly suggested binding of one pentanal molecule to the amino terminal proline and three pentanal molecules bound to the lysine residue. The latter species is suggested to be the actual fluorophore, through the formation of conjugated double bonds, and a possible reaction pathway through a combination of aldol condensation of pentanal and Schiff base formation with the lysine is suggested. Keywords: Carbonyl modifications; Schiff base formation; aldol condensation; peptides; fluorescence spectroscopy; MALDI TOF MS-MS; fluorophore; lipid oxidation</description><subject>aldehydes</subject><subject>Aldehydes - chemistry</subject><subject>Amino Acid Sequence</subject><subject>Biological and medical sciences</subject><subject>chemical reactions</subject><subject>fluorescence emission spectroscopy</subject><subject>fluorophores</subject><subject>food chemistry</subject><subject>Food industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>gas chromatography</subject><subject>lysine</subject><subject>Lysine - analysis</subject><subject>Lysine - chemistry</subject><subject>Mass Spectrometry</subject><subject>oligopeptides</subject><subject>Oligopeptides - chemistry</subject><subject>pentanal</subject><subject>reaction mechanisms</subject><subject>reaction products</subject><subject>Schiff bases</subject><subject>Spectrometry, Fluorescence</subject><subject>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0UFv0zAUB3ALgVgZHPgCkAtIHALPSew4x6nQglTYxLaz9eo8F5fULnYiGJ8eT63WCydbfj892__H2EsO7zlU_MPWggSAevOIzbiooBScq8dsBrlYKiH5GXuW0jYTJVp4ys647Di0dTVj0_wHRjQjRfcXRxd8EWzxnfLJ_f4qhn4yYyoWIe6oL5wvsPgaehpOZk3jb6JsyY_ocSjQ98XqLjlP5TzkM-ed3xSXg9uEPe1H11N6zp5YHBK9OK7n7Hbx6Wb-uVxdLr_ML1YlNiDG0kglLe9Eb42VreiQOiubupGIwPuuBbKtgtqorm7W1FcERpKxDciepORdfc7eHvruY_g1URr1ziVDw4CewpS0VK2ooWkyfHeAJoaUIlm9j26H8U5z0PcZ64eMs311bDqtcygneQw1gzdHgMngYCN649LJKWhEfnJ25cG5NNKfhzrGn1q2dSv0zdW1XlTw8VullnqZ_euDtxg0bmLueXtdAa-Bc8hjV6eb0SS9DVPM80j_-cI_dQCo3w</recordid><startdate>20060823</startdate><enddate>20060823</enddate><creator>Dalsgaard, Trine K</creator><creator>Nielsen, Jacob H</creator><creator>Larsen, Lotte B</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20060823</creationdate><title>Characterization of Reaction Products Formed in a Model Reaction between Pentanal and Lysine-Containing Oligopeptides</title><author>Dalsgaard, Trine K ; Nielsen, Jacob H ; Larsen, Lotte B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a405t-c686f195dfcf6759ae9f64346aa01d970ef7803c8934bed2e0c6ecf406de66193</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>aldehydes</topic><topic>Aldehydes - chemistry</topic><topic>Amino Acid Sequence</topic><topic>Biological and medical sciences</topic><topic>chemical reactions</topic><topic>fluorescence emission spectroscopy</topic><topic>fluorophores</topic><topic>food chemistry</topic><topic>Food industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>gas chromatography</topic><topic>lysine</topic><topic>Lysine - analysis</topic><topic>Lysine - chemistry</topic><topic>Mass Spectrometry</topic><topic>oligopeptides</topic><topic>Oligopeptides - chemistry</topic><topic>pentanal</topic><topic>reaction mechanisms</topic><topic>reaction products</topic><topic>Schiff bases</topic><topic>Spectrometry, Fluorescence</topic><topic>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dalsgaard, Trine K</creatorcontrib><creatorcontrib>Nielsen, Jacob H</creatorcontrib><creatorcontrib>Larsen, Lotte B</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dalsgaard, Trine K</au><au>Nielsen, Jacob H</au><au>Larsen, Lotte B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Characterization of Reaction Products Formed in a Model Reaction between Pentanal and Lysine-Containing Oligopeptides</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2006-08-23</date><risdate>2006</risdate><volume>54</volume><issue>17</issue><spage>6367</spage><epage>6373</epage><pages>6367-6373</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Aldehydes formed as a result of lipid oxidation form fluorophores after binding to proteins. The structure of the fluorophores formed by reaction between saturated aldehydes and lysine has not yet been identified. The reaction products formed in the reaction between pentanal and oligopeptides were studied by fluorescence spectroscopy and mass spectrometry. The emission spectra showed an increase in fluorescence intensity with incubation time, and the rates were linear with the concentration of pentanal. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry analyses of the reaction products suggested a molar relation for peptide:pentanal of 1:4. Further tandem mass spectrometry analysis of one of the modified peptides (Pro-Thr-His-Ile-Lys-Trp-Gly-Asp) strongly suggested binding of one pentanal molecule to the amino terminal proline and three pentanal molecules bound to the lysine residue. The latter species is suggested to be the actual fluorophore, through the formation of conjugated double bonds, and a possible reaction pathway through a combination of aldol condensation of pentanal and Schiff base formation with the lysine is suggested. Keywords: Carbonyl modifications; Schiff base formation; aldol condensation; peptides; fluorescence spectroscopy; MALDI TOF MS-MS; fluorophore; lipid oxidation</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16910732</pmid><doi>10.1021/jf060003g</doi><tpages>7</tpages></addata></record> |
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| subjects | aldehydes Aldehydes - chemistry Amino Acid Sequence Biological and medical sciences chemical reactions fluorescence emission spectroscopy fluorophores food chemistry Food industries Fundamental and applied biological sciences. Psychology gas chromatography lysine Lysine - analysis Lysine - chemistry Mass Spectrometry oligopeptides Oligopeptides - chemistry pentanal reaction mechanisms reaction products Schiff bases Spectrometry, Fluorescence Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization |
| title | Characterization of Reaction Products Formed in a Model Reaction between Pentanal and Lysine-Containing Oligopeptides |
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