Determination of δ‐[L‐α‐aminoadipyl]‐L‐cysteinyl‐D‐valine in cell extracts of Penicillium chrysogenum using ion pair‐RP‐UPLC‐MS/MS
δ‐[L‐α‐Aminoadipyl]‐L‐cysteinyl‐D‐valine (ACV) is a key intermediate in the biosynthesis pathway of penicillins and cephalosporins. Therefore, the accurate quantification of ACV is relevant, e.g. for kinetic studies on the production of these β‐lactam antibiotics. However, accurate quantification of...
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| Veröffentlicht in: | Journal of separation science 2012, Vol.35 (2), p.225-230 |
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| creator | Seifar, Reza Maleki Deshmukh, Amit T Heijnen, Joseph J van Gulik, Walter M |
| description | δ‐[L‐α‐Aminoadipyl]‐L‐cysteinyl‐D‐valine (ACV) is a key intermediate in the biosynthesis pathway of penicillins and cephalosporins. Therefore, the accurate quantification of ACV is relevant, e.g. for kinetic studies on the production of these β‐lactam antibiotics. However, accurate quantification of ACV is a challenge, because it is an active thiol compound which, upon exposure to air, can easily react with other thiol compounds to form oxidized disulfides. We have found that, during exposure to air, the oxidation of ACV occurs both in aqueous standard solutions as well as in biological samples. Qualitative and quantitative determinations of ACV and the oxidized dimer bis‐δ‐[L‐α‐aminoadipyl]‐L‐cysteinyl‐D‐valine have been carried out using ion pair reversed‐phase ultra high‐performance liquid chromatography, hyphenated with tandem mass spectrometry (IP‐RP‐UPLC‐MS/MS) as the analytical platform. We show that by application of tris(2‐carboxy‐ethyl)phosphine hydrochloride (TCEP) as the reducing reagent, the total amount of ACV can be determined, while using maleimide as derivatizing reagent enables to quantify the free reduced form only. |
| doi_str_mv | 10.1002/jssc.201100527 |
| format | Article |
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Therefore, the accurate quantification of ACV is relevant, e.g. for kinetic studies on the production of these β‐lactam antibiotics. However, accurate quantification of ACV is a challenge, because it is an active thiol compound which, upon exposure to air, can easily react with other thiol compounds to form oxidized disulfides. We have found that, during exposure to air, the oxidation of ACV occurs both in aqueous standard solutions as well as in biological samples. Qualitative and quantitative determinations of ACV and the oxidized dimer bis‐δ‐[L‐α‐aminoadipyl]‐L‐cysteinyl‐D‐valine have been carried out using ion pair reversed‐phase ultra high‐performance liquid chromatography, hyphenated with tandem mass spectrometry (IP‐RP‐UPLC‐MS/MS) as the analytical platform. We show that by application of tris(2‐carboxy‐ethyl)phosphine hydrochloride (TCEP) as the reducing reagent, the total amount of ACV can be determined, while using maleimide as derivatizing reagent enables to quantify the free reduced form only.</description><identifier>ISSN: 1615-9306</identifier><identifier>EISSN: 1615-9314</identifier><identifier>DOI: 10.1002/jssc.201100527</identifier><identifier>PMID: 25939821</identifier><language>eng</language><publisher>Weinheim: WILEY‐VCH Verlag</publisher><subject>Anti-Bacterial Agents - biosynthesis ; Antibiotics (antibacterial agents, antifungal agents) ; Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents ; Applied microbiology ; beta-Lactams - metabolism ; Biological ; Biological and medical sciences ; biosynthesis ; Cell extract ; cephalosporins ; Chromatography, High Pressure Liquid - methods ; Chromatography, Reverse-Phase - methods ; Fundamental and applied biological sciences. Psychology ; Indicators and Reagents ; Liquid chromatography ; Maleimide ; Maleimides ; Mass spectrometry ; Mathematical analysis ; Microbiology ; Oligopeptides - analysis ; Oligopeptides - chemistry ; Oligopeptides - metabolism ; oxidation ; Oxidation-Reduction ; Penicillin ; penicillins ; Penicillium chrysogenum ; Penicillium chrysogenum - chemistry ; Penicillium chrysogenum - metabolism ; phosphine ; Phosphines ; Separation ; Tandem Mass Spectrometry - methods ; TCEP ; Thiols</subject><ispartof>Journal of separation science, 2012, Vol.35 (2), p.225-230</ispartof><rights>Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4707-4f566a493d891c093ea45f7cbafc6640b589f09f8529e3ee97ab5309cd987c093</citedby><cites>FETCH-LOGICAL-c4707-4f566a493d891c093ea45f7cbafc6640b589f09f8529e3ee97ab5309cd987c093</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjssc.201100527$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjssc.201100527$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,4024,27923,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25399692$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25939821$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Seifar, Reza Maleki</creatorcontrib><creatorcontrib>Deshmukh, Amit T</creatorcontrib><creatorcontrib>Heijnen, Joseph J</creatorcontrib><creatorcontrib>van Gulik, Walter M</creatorcontrib><title>Determination of δ‐[L‐α‐aminoadipyl]‐L‐cysteinyl‐D‐valine in cell extracts of Penicillium chrysogenum using ion pair‐RP‐UPLC‐MS/MS</title><title>Journal of separation science</title><addtitle>J. Sep. Science</addtitle><description>δ‐[L‐α‐Aminoadipyl]‐L‐cysteinyl‐D‐valine (ACV) is a key intermediate in the biosynthesis pathway of penicillins and cephalosporins. Therefore, the accurate quantification of ACV is relevant, e.g. for kinetic studies on the production of these β‐lactam antibiotics. However, accurate quantification of ACV is a challenge, because it is an active thiol compound which, upon exposure to air, can easily react with other thiol compounds to form oxidized disulfides. We have found that, during exposure to air, the oxidation of ACV occurs both in aqueous standard solutions as well as in biological samples. Qualitative and quantitative determinations of ACV and the oxidized dimer bis‐δ‐[L‐α‐aminoadipyl]‐L‐cysteinyl‐D‐valine have been carried out using ion pair reversed‐phase ultra high‐performance liquid chromatography, hyphenated with tandem mass spectrometry (IP‐RP‐UPLC‐MS/MS) as the analytical platform. We show that by application of tris(2‐carboxy‐ethyl)phosphine hydrochloride (TCEP) as the reducing reagent, the total amount of ACV can be determined, while using maleimide as derivatizing reagent enables to quantify the free reduced form only.</description><subject>Anti-Bacterial Agents - biosynthesis</subject><subject>Antibiotics (antibacterial agents, antifungal agents)</subject><subject>Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents</subject><subject>Applied microbiology</subject><subject>beta-Lactams - metabolism</subject><subject>Biological</subject><subject>Biological and medical sciences</subject><subject>biosynthesis</subject><subject>Cell extract</subject><subject>cephalosporins</subject><subject>Chromatography, High Pressure Liquid - methods</subject><subject>Chromatography, Reverse-Phase - methods</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Indicators and Reagents</subject><subject>Liquid chromatography</subject><subject>Maleimide</subject><subject>Maleimides</subject><subject>Mass spectrometry</subject><subject>Mathematical analysis</subject><subject>Microbiology</subject><subject>Oligopeptides - analysis</subject><subject>Oligopeptides - chemistry</subject><subject>Oligopeptides - metabolism</subject><subject>oxidation</subject><subject>Oxidation-Reduction</subject><subject>Penicillin</subject><subject>penicillins</subject><subject>Penicillium chrysogenum</subject><subject>Penicillium chrysogenum - chemistry</subject><subject>Penicillium chrysogenum - metabolism</subject><subject>phosphine</subject><subject>Phosphines</subject><subject>Separation</subject><subject>Tandem Mass Spectrometry - methods</subject><subject>TCEP</subject><subject>Thiols</subject><issn>1615-9306</issn><issn>1615-9314</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU9u1DAUxiMEoqWwZQnZILHJ1H9iJ17CFAplWkakIyQQsjwee3BxnMFOoNlxBJZcA4lz9BCcBEcZRt114edn-_e-Z_tLkocQTCAA6PAiBDlBAMYFQcWtZB9SSDKGYX57lwO6l9wL4QIAWJQM3E32EGGYlQjuJ7-OVKt8bZxoTePSRqdXf_7--PlxFsPV7xhEPGvEymx6-ykuh33Zh1YZ19uYH8XxTVjjVGpcKpW1qbpsvZBtGMTmyhlprDVdncrPvg_NWrmYd8G4dTp03Ajjo8a7eQyL-Wwap9Pq8LS6n9zRwgb1YDsfJIuXL86nr7LZ2-PX02ezTOYFKLJcE0pFzvCqZFAChpXIiS7kUmhJaQ6WpGQaMF0SxBRWihViSTBgcsXKYuAPkqej7sY3XzsVWl6bMLxDONV0gUNaAlgCRvHNKECIQURJGdHJiErfhOCV5htvauH7CPHBOD4Yx3fGxYJHW-1uWavVDv_vVASebAERpLDaCydNuMZhxihDkWMj991Y1d_Qlp9U1fT6JbKx1kSDL3e1wn_htMAF4e_PjvnJ-Qd69uY54MPfPR55LRou1j7eZ1FFuRwAwOKvQfwPDfLWVQ</recordid><startdate>2012</startdate><enddate>2012</enddate><creator>Seifar, Reza Maleki</creator><creator>Deshmukh, Amit T</creator><creator>Heijnen, Joseph J</creator><creator>van Gulik, Walter M</creator><general>WILEY‐VCH Verlag</general><general>WILEY-VCH Verlag</general><general>Wiley</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>7U5</scope><scope>8FD</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>2012</creationdate><title>Determination of δ‐[L‐α‐aminoadipyl]‐L‐cysteinyl‐D‐valine in cell extracts of Penicillium chrysogenum using ion pair‐RP‐UPLC‐MS/MS</title><author>Seifar, Reza Maleki ; Deshmukh, Amit T ; Heijnen, Joseph J ; van Gulik, Walter M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4707-4f566a493d891c093ea45f7cbafc6640b589f09f8529e3ee97ab5309cd987c093</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Anti-Bacterial Agents - biosynthesis</topic><topic>Antibiotics (antibacterial agents, antifungal agents)</topic><topic>Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents</topic><topic>Applied microbiology</topic><topic>beta-Lactams - metabolism</topic><topic>Biological</topic><topic>Biological and medical sciences</topic><topic>biosynthesis</topic><topic>Cell extract</topic><topic>cephalosporins</topic><topic>Chromatography, High Pressure Liquid - methods</topic><topic>Chromatography, Reverse-Phase - methods</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Indicators and Reagents</topic><topic>Liquid chromatography</topic><topic>Maleimide</topic><topic>Maleimides</topic><topic>Mass spectrometry</topic><topic>Mathematical analysis</topic><topic>Microbiology</topic><topic>Oligopeptides - analysis</topic><topic>Oligopeptides - chemistry</topic><topic>Oligopeptides - metabolism</topic><topic>oxidation</topic><topic>Oxidation-Reduction</topic><topic>Penicillin</topic><topic>penicillins</topic><topic>Penicillium chrysogenum</topic><topic>Penicillium chrysogenum - chemistry</topic><topic>Penicillium chrysogenum - metabolism</topic><topic>phosphine</topic><topic>Phosphines</topic><topic>Separation</topic><topic>Tandem Mass Spectrometry - methods</topic><topic>TCEP</topic><topic>Thiols</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Seifar, Reza Maleki</creatorcontrib><creatorcontrib>Deshmukh, Amit T</creatorcontrib><creatorcontrib>Heijnen, Joseph J</creatorcontrib><creatorcontrib>van Gulik, Walter M</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>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of separation science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Seifar, Reza Maleki</au><au>Deshmukh, Amit T</au><au>Heijnen, Joseph J</au><au>van Gulik, Walter M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Determination of δ‐[L‐α‐aminoadipyl]‐L‐cysteinyl‐D‐valine in cell extracts of Penicillium chrysogenum using ion pair‐RP‐UPLC‐MS/MS</atitle><jtitle>Journal of separation science</jtitle><addtitle>J. Sep. Science</addtitle><date>2012</date><risdate>2012</risdate><volume>35</volume><issue>2</issue><spage>225</spage><epage>230</epage><pages>225-230</pages><issn>1615-9306</issn><eissn>1615-9314</eissn><abstract>δ‐[L‐α‐Aminoadipyl]‐L‐cysteinyl‐D‐valine (ACV) is a key intermediate in the biosynthesis pathway of penicillins and cephalosporins. Therefore, the accurate quantification of ACV is relevant, e.g. for kinetic studies on the production of these β‐lactam antibiotics. However, accurate quantification of ACV is a challenge, because it is an active thiol compound which, upon exposure to air, can easily react with other thiol compounds to form oxidized disulfides. We have found that, during exposure to air, the oxidation of ACV occurs both in aqueous standard solutions as well as in biological samples. Qualitative and quantitative determinations of ACV and the oxidized dimer bis‐δ‐[L‐α‐aminoadipyl]‐L‐cysteinyl‐D‐valine have been carried out using ion pair reversed‐phase ultra high‐performance liquid chromatography, hyphenated with tandem mass spectrometry (IP‐RP‐UPLC‐MS/MS) as the analytical platform. We show that by application of tris(2‐carboxy‐ethyl)phosphine hydrochloride (TCEP) as the reducing reagent, the total amount of ACV can be determined, while using maleimide as derivatizing reagent enables to quantify the free reduced form only.</abstract><cop>Weinheim</cop><pub>WILEY‐VCH Verlag</pub><pmid>25939821</pmid><doi>10.1002/jssc.201100527</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of separation science, 2012, Vol.35 (2), p.225-230 |
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| subjects | Anti-Bacterial Agents - biosynthesis Antibiotics (antibacterial agents, antifungal agents) Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents Applied microbiology beta-Lactams - metabolism Biological Biological and medical sciences biosynthesis Cell extract cephalosporins Chromatography, High Pressure Liquid - methods Chromatography, Reverse-Phase - methods Fundamental and applied biological sciences. Psychology Indicators and Reagents Liquid chromatography Maleimide Maleimides Mass spectrometry Mathematical analysis Microbiology Oligopeptides - analysis Oligopeptides - chemistry Oligopeptides - metabolism oxidation Oxidation-Reduction Penicillin penicillins Penicillium chrysogenum Penicillium chrysogenum - chemistry Penicillium chrysogenum - metabolism phosphine Phosphines Separation Tandem Mass Spectrometry - methods TCEP Thiols |
| title | Determination of δ‐[L‐α‐aminoadipyl]‐L‐cysteinyl‐D‐valine in cell extracts of Penicillium chrysogenum using ion pair‐RP‐UPLC‐MS/MS |
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