Molecular Formula Analysis by an MS/MS/MS Technique To Expedite Dereplication of Natural Products
A facile and sensitive mass spectrometric method has been developed for the dereplication of natural products. The method provides information about the molecular formula and substructure of a precursor molecule and its fragments, which are invaluable aids in dereplication of natural products at the...
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| Veröffentlicht in: | Analytical chemistry (Washington) 2007-02, Vol.79 (3), p.1187-1197 |
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| creator | Konishi, Yasuo Kiyota, Taira Draghici, Cristina Gao, Jin-Ming Yeboah, Faustinus Acoca, Stephane Jarussophon, Suwatchai Purisima, Enrico |
| description | A facile and sensitive mass spectrometric method has been developed for the dereplication of natural products. The method provides information about the molecular formula and substructure of a precursor molecule and its fragments, which are invaluable aids in dereplication of natural products at their early stages of purification and characterization. Collision-induced MS/MS technique is used to fragment a precursor ion into several product ions, and individual product ions are selected and subjected to collision-induced MS/MS/MS analysis. This method enables the identification of the fragmentation pathway of a precursor molecule from its first-generation fragments (MS/MS), through to the nth generation product ions (MS n ). It also allows for the identification of the corresponding neutral products released (neutral losses). Elements used in the molecular formula analysis include C, H, N, O, and S, as most natural products are constituted by these five elements. High-resolution mass separation and accurate mass measurements afforded the unique identification of molecular formula of small neutral products. Through sequential add-up of the molecular formulas of the small neutral products, the molecular formula of the precursor ion and its productions were uniquely determined. The molecular formula of the precursor molecule was then reversely used to identify or confirm the molecular formula of the neutral products and that of the productions. The molecular formula of the neutral fragments allowed for the identification of substructures, leading to a rapid and efficient characterization of precursor natural product. The method was applied to paclitaxel (C47H51NO14; 853 amu) to identify its molecular formula and its substructures, and to characterize its potential fragmentation pathways. The method was further validated by correctly identifying the molecular formula of minocycline (C23H27N3O7; 457 amu) and piperacillin (C23H27N5O7S; 517 amu). |
| doi_str_mv | 10.1021/ac061391o |
| format | Article |
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The method provides information about the molecular formula and substructure of a precursor molecule and its fragments, which are invaluable aids in dereplication of natural products at their early stages of purification and characterization. Collision-induced MS/MS technique is used to fragment a precursor ion into several product ions, and individual product ions are selected and subjected to collision-induced MS/MS/MS analysis. This method enables the identification of the fragmentation pathway of a precursor molecule from its first-generation fragments (MS/MS), through to the nth generation product ions (MS n ). It also allows for the identification of the corresponding neutral products released (neutral losses). Elements used in the molecular formula analysis include C, H, N, O, and S, as most natural products are constituted by these five elements. High-resolution mass separation and accurate mass measurements afforded the unique identification of molecular formula of small neutral products. Through sequential add-up of the molecular formulas of the small neutral products, the molecular formula of the precursor ion and its productions were uniquely determined. The molecular formula of the precursor molecule was then reversely used to identify or confirm the molecular formula of the neutral products and that of the productions. The molecular formula of the neutral fragments allowed for the identification of substructures, leading to a rapid and efficient characterization of precursor natural product. The method was applied to paclitaxel (C47H51NO14; 853 amu) to identify its molecular formula and its substructures, and to characterize its potential fragmentation pathways. The method was further validated by correctly identifying the molecular formula of minocycline (C23H27N3O7; 457 amu) and piperacillin (C23H27N5O7S; 517 amu).</description><identifier>ISSN: 0003-2700</identifier><identifier>EISSN: 1520-6882</identifier><identifier>DOI: 10.1021/ac061391o</identifier><identifier>PMID: 17263353</identifier><identifier>CODEN: ANCHAM</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Analytical chemistry ; Biological Products - chemistry ; Chemistry ; Elements ; Exact sciences and technology ; Mass spectrometry ; Molecular biology ; Molecular Structure ; Spectrometric and optical methods ; Tandem Mass Spectrometry - methods</subject><ispartof>Analytical chemistry (Washington), 2007-02, Vol.79 (3), p.1187-1197</ispartof><rights>Copyright © 2007 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><rights>Copyright American Chemical Society Feb 1, 2007</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a538t-ac5562efb6692f029970a1d9f4072003c0a58ee851905d1bd06471aa85b05f963</citedby><cites>FETCH-LOGICAL-a538t-ac5562efb6692f029970a1d9f4072003c0a58ee851905d1bd06471aa85b05f963</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/ac061391o$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ac061391o$$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=18517409$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17263353$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Konishi, Yasuo</creatorcontrib><creatorcontrib>Kiyota, Taira</creatorcontrib><creatorcontrib>Draghici, Cristina</creatorcontrib><creatorcontrib>Gao, Jin-Ming</creatorcontrib><creatorcontrib>Yeboah, Faustinus</creatorcontrib><creatorcontrib>Acoca, Stephane</creatorcontrib><creatorcontrib>Jarussophon, Suwatchai</creatorcontrib><creatorcontrib>Purisima, Enrico</creatorcontrib><title>Molecular Formula Analysis by an MS/MS/MS Technique To Expedite Dereplication of Natural Products</title><title>Analytical chemistry (Washington)</title><addtitle>Anal. Chem</addtitle><description>A facile and sensitive mass spectrometric method has been developed for the dereplication of natural products. The method provides information about the molecular formula and substructure of a precursor molecule and its fragments, which are invaluable aids in dereplication of natural products at their early stages of purification and characterization. Collision-induced MS/MS technique is used to fragment a precursor ion into several product ions, and individual product ions are selected and subjected to collision-induced MS/MS/MS analysis. This method enables the identification of the fragmentation pathway of a precursor molecule from its first-generation fragments (MS/MS), through to the nth generation product ions (MS n ). It also allows for the identification of the corresponding neutral products released (neutral losses). Elements used in the molecular formula analysis include C, H, N, O, and S, as most natural products are constituted by these five elements. High-resolution mass separation and accurate mass measurements afforded the unique identification of molecular formula of small neutral products. Through sequential add-up of the molecular formulas of the small neutral products, the molecular formula of the precursor ion and its productions were uniquely determined. The molecular formula of the precursor molecule was then reversely used to identify or confirm the molecular formula of the neutral products and that of the productions. The molecular formula of the neutral fragments allowed for the identification of substructures, leading to a rapid and efficient characterization of precursor natural product. The method was applied to paclitaxel (C47H51NO14; 853 amu) to identify its molecular formula and its substructures, and to characterize its potential fragmentation pathways. The method was further validated by correctly identifying the molecular formula of minocycline (C23H27N3O7; 457 amu) and piperacillin (C23H27N5O7S; 517 amu).</description><subject>Analytical chemistry</subject><subject>Biological Products - chemistry</subject><subject>Chemistry</subject><subject>Elements</subject><subject>Exact sciences and technology</subject><subject>Mass spectrometry</subject><subject>Molecular biology</subject><subject>Molecular Structure</subject><subject>Spectrometric and optical methods</subject><subject>Tandem Mass Spectrometry - methods</subject><issn>0003-2700</issn><issn>1520-6882</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNplkNFrFDEQxoMo9qw--A9IEBR8WDvJXpLNY6ltFa7a2tPXMJvNYmpuc012offfN-0dPVAYmIH58c18HyFvGXxmwNkRWpCs1iw-IzMmOFSyafhzMgOAuuIK4IC8yvkGgDFg8iU5YIrLuhb1jOBFDM5OARM9i2lVBno8YNhkn2m7oTjQi-ujx6JLZ_8M_nZydBnp6d3adX509ItLbh28xdHHgcaefsdxShjoZYrdZMf8mrzoMWT3ZtcPya-z0-XJ12rx4_zbyfGiQlE3Y4VWCMld30qpeQ9cawXIOt3PQfHiwwKKxrlGMA2iY20Hcq4YYiNaEL2W9SH5uNVdp1iezKNZ-WxdCDi4OGUjGy2ZUg_g-3_AmzilYjobzlSjS0i6QJ-2kE0x5-R6s05-hWljGJiH0M1T6IV9txOc2pXr9uQu5QJ82AGYLYY-4WB93nPFlJo_Hq22nM-ju3vaY_prpKqVMMvLa3P1e9Hw-c8rw_e6aPPexP8P3gM0EaH0</recordid><startdate>20070201</startdate><enddate>20070201</enddate><creator>Konishi, Yasuo</creator><creator>Kiyota, Taira</creator><creator>Draghici, Cristina</creator><creator>Gao, Jin-Ming</creator><creator>Yeboah, Faustinus</creator><creator>Acoca, Stephane</creator><creator>Jarussophon, Suwatchai</creator><creator>Purisima, Enrico</creator><general>American Chemical Society</general><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>7QF</scope><scope>7QO</scope><scope>7QQ</scope><scope>7SC</scope><scope>7SE</scope><scope>7SP</scope><scope>7SR</scope><scope>7TA</scope><scope>7TB</scope><scope>7TM</scope><scope>7U5</scope><scope>7U7</scope><scope>7U9</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>F28</scope><scope>FR3</scope><scope>H8D</scope><scope>H8G</scope><scope>H94</scope><scope>JG9</scope><scope>JQ2</scope><scope>KR7</scope><scope>L7M</scope><scope>L~C</scope><scope>L~D</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20070201</creationdate><title>Molecular Formula Analysis by an MS/MS/MS Technique To Expedite Dereplication of Natural Products</title><author>Konishi, Yasuo ; Kiyota, Taira ; Draghici, Cristina ; Gao, Jin-Ming ; Yeboah, Faustinus ; Acoca, Stephane ; Jarussophon, Suwatchai ; Purisima, Enrico</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a538t-ac5562efb6692f029970a1d9f4072003c0a58ee851905d1bd06471aa85b05f963</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Analytical chemistry</topic><topic>Biological Products - chemistry</topic><topic>Chemistry</topic><topic>Elements</topic><topic>Exact sciences and technology</topic><topic>Mass spectrometry</topic><topic>Molecular biology</topic><topic>Molecular Structure</topic><topic>Spectrometric and optical methods</topic><topic>Tandem Mass Spectrometry - methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Konishi, Yasuo</creatorcontrib><creatorcontrib>Kiyota, Taira</creatorcontrib><creatorcontrib>Draghici, Cristina</creatorcontrib><creatorcontrib>Gao, Jin-Ming</creatorcontrib><creatorcontrib>Yeboah, Faustinus</creatorcontrib><creatorcontrib>Acoca, Stephane</creatorcontrib><creatorcontrib>Jarussophon, Suwatchai</creatorcontrib><creatorcontrib>Purisima, Enrico</creatorcontrib><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>Aluminium Industry Abstracts</collection><collection>Biotechnology Research Abstracts</collection><collection>Ceramic Abstracts</collection><collection>Computer and Information Systems Abstracts</collection><collection>Corrosion Abstracts</collection><collection>Electronics & Communications Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>Materials Business File</collection><collection>Mechanical & Transportation Engineering Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ANTE: Abstracts in New Technology & Engineering</collection><collection>Engineering Research Database</collection><collection>Aerospace Database</collection><collection>Copper Technical Reference Library</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Materials Research Database</collection><collection>ProQuest Computer Science Collection</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Computer and Information Systems Abstracts Academic</collection><collection>Computer and Information Systems Abstracts Professional</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Analytical chemistry (Washington)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Konishi, Yasuo</au><au>Kiyota, Taira</au><au>Draghici, Cristina</au><au>Gao, Jin-Ming</au><au>Yeboah, Faustinus</au><au>Acoca, Stephane</au><au>Jarussophon, Suwatchai</au><au>Purisima, Enrico</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Molecular Formula Analysis by an MS/MS/MS Technique To Expedite Dereplication of Natural Products</atitle><jtitle>Analytical chemistry (Washington)</jtitle><addtitle>Anal. Chem</addtitle><date>2007-02-01</date><risdate>2007</risdate><volume>79</volume><issue>3</issue><spage>1187</spage><epage>1197</epage><pages>1187-1197</pages><issn>0003-2700</issn><eissn>1520-6882</eissn><coden>ANCHAM</coden><abstract>A facile and sensitive mass spectrometric method has been developed for the dereplication of natural products. The method provides information about the molecular formula and substructure of a precursor molecule and its fragments, which are invaluable aids in dereplication of natural products at their early stages of purification and characterization. Collision-induced MS/MS technique is used to fragment a precursor ion into several product ions, and individual product ions are selected and subjected to collision-induced MS/MS/MS analysis. This method enables the identification of the fragmentation pathway of a precursor molecule from its first-generation fragments (MS/MS), through to the nth generation product ions (MS n ). It also allows for the identification of the corresponding neutral products released (neutral losses). Elements used in the molecular formula analysis include C, H, N, O, and S, as most natural products are constituted by these five elements. High-resolution mass separation and accurate mass measurements afforded the unique identification of molecular formula of small neutral products. Through sequential add-up of the molecular formulas of the small neutral products, the molecular formula of the precursor ion and its productions were uniquely determined. The molecular formula of the precursor molecule was then reversely used to identify or confirm the molecular formula of the neutral products and that of the productions. The molecular formula of the neutral fragments allowed for the identification of substructures, leading to a rapid and efficient characterization of precursor natural product. The method was applied to paclitaxel (C47H51NO14; 853 amu) to identify its molecular formula and its substructures, and to characterize its potential fragmentation pathways. The method was further validated by correctly identifying the molecular formula of minocycline (C23H27N3O7; 457 amu) and piperacillin (C23H27N5O7S; 517 amu).</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17263353</pmid><doi>10.1021/ac061391o</doi><tpages>11</tpages></addata></record> |
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| subjects | Analytical chemistry Biological Products - chemistry Chemistry Elements Exact sciences and technology Mass spectrometry Molecular biology Molecular Structure Spectrometric and optical methods Tandem Mass Spectrometry - methods |
| title | Molecular Formula Analysis by an MS/MS/MS Technique To Expedite Dereplication of Natural Products |
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