Analysis of dna-phosphate adducts in vitro using miniaturized lc-esi-ms/ms and column switching: phosphotriesters and alkyl cobalamins
DNA-phosphate adducts are known to be formed by a variety of alkylating agents. Due to little or no repair of DNA-phosphate adducts, these adducts may offer increased possibilities of both identifying and quantifying DNA adducts. The formation of DNA-phosphate adducts leads to a complete esterificat...
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| Veröffentlicht in: | Journal of the American Society for Mass Spectrometry 2004-04, Vol.15 (4), p.593-606 |
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| creator | Haglund, Johanna Van Dongen, Walter Lemière, Filip Esmans, Eddy L |
| description | DNA-phosphate adducts are known to be formed by a variety of alkylating agents. Due to little or no repair of DNA-phosphate adducts, these adducts may offer increased possibilities of both identifying and quantifying DNA adducts. The formation of DNA-phosphate adducts leads to a complete esterification of the phosphate group giving rise to a phosphotriester configuration. This work consists of the characterization of ethyl phosphotriesters (Ethyl PTE) using miniaturized LC-ESI-MS/MS and column switching in enzymatic hydrolysate of DNA treated in vitro with the model compound
N-ethyl-
N-nitrosourea (ENU). In vitro ENU-treated DNA was enzymatically degraded using nuclease P1, phosphodiesterase, and alkaline phosphatase. The use of column switch allowed for large-volume injections, where unmodified nucleosides were discarded in the loading step. The analytes were forward flushed to the analytical column in the eluting step and separated using a linear gradient. Ten different ethyl PTEs (dGpEtdG, dApEtdA, dCpEtdC, TpEtT, dGpEtdA, dGpEtdC, dGpEtT, dApEtdC, dApEtT, and dCpEtT) were characterized by their masses and CAD product ion spectra. Measurements of accurate masses were carried out yielding experimental masses within 5 ppm of the calculated masses for 9 of the 10 ethyl PTEs. For comparison, the enzymatic hydrolysate of ENU-treated DNA was subjected to transalkylation of the DNA-phosphate adducts by cob(I)alamin. Formed ethyl-cobalamins were analyzed according to earlier developed methods. The limit of detection of an alkyl-cobalamin standard and an alkyl PTE standard was 2 fmol and 5 fmol, respectively. |
| doi_str_mv | 10.1016/j.jasms.2003.12.012 |
| format | Article |
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N-ethyl-
N-nitrosourea (ENU). In vitro ENU-treated DNA was enzymatically degraded using nuclease P1, phosphodiesterase, and alkaline phosphatase. The use of column switch allowed for large-volume injections, where unmodified nucleosides were discarded in the loading step. The analytes were forward flushed to the analytical column in the eluting step and separated using a linear gradient. Ten different ethyl PTEs (dGpEtdG, dApEtdA, dCpEtdC, TpEtT, dGpEtdA, dGpEtdC, dGpEtT, dApEtdC, dApEtT, and dCpEtT) were characterized by their masses and CAD product ion spectra. Measurements of accurate masses were carried out yielding experimental masses within 5 ppm of the calculated masses for 9 of the 10 ethyl PTEs. For comparison, the enzymatic hydrolysate of ENU-treated DNA was subjected to transalkylation of the DNA-phosphate adducts by cob(I)alamin. Formed ethyl-cobalamins were analyzed according to earlier developed methods. The limit of detection of an alkyl-cobalamin standard and an alkyl PTE standard was 2 fmol and 5 fmol, respectively.</description><identifier>ISSN: 1044-0305</identifier><identifier>EISSN: 1879-1123</identifier><identifier>DOI: 10.1016/j.jasms.2003.12.012</identifier><identifier>PMID: 15047064</identifier><language>eng</language><publisher>New York, NY: Elsevier Inc</publisher><subject>Adducts ; Alkaline phosphatase ; Alkylation ; Analytical biochemistry: general aspects, technics, instrumentation ; Analytical, structural and metabolic biochemistry ; Animals ; Biological and medical sciences ; Cattle ; Deoxyribonucleic acid ; DNA ; DNA Adducts - analysis ; DNA Adducts - chemistry ; Esterification ; Fundamental and applied biological sciences. Psychology ; Isomerism ; Mass spectrometry ; Mass Spectrometry - instrumentation ; Mass Spectrometry - methods ; Molecular Structure ; Nuclease ; Phosphates - analysis ; Reproducibility of Results ; Sensitivity and Specificity ; Spectrometry, Mass, Electrospray Ionization ; Switching ; Thymus Gland ; Transalkylation ; Vitamin B 12 - analysis ; Vitamin B 12 - chemistry</subject><ispartof>Journal of the American Society for Mass Spectrometry, 2004-04, Vol.15 (4), p.593-606</ispartof><rights>2004 American Society for Mass Spectrometry</rights><rights>2004 INIST-CNRS</rights><rights>American Society for Mass Spectrometry 2004</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c458t-49aef2d0c58d073ef720418cc56b921cd2142ec6dcdb0ab13c107a0d7b544e723</citedby><cites>FETCH-LOGICAL-c458t-49aef2d0c58d073ef720418cc56b921cd2142ec6dcdb0ab13c107a0d7b544e723</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15626498$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15047064$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Haglund, Johanna</creatorcontrib><creatorcontrib>Van Dongen, Walter</creatorcontrib><creatorcontrib>Lemière, Filip</creatorcontrib><creatorcontrib>Esmans, Eddy L</creatorcontrib><title>Analysis of dna-phosphate adducts in vitro using miniaturized lc-esi-ms/ms and column switching: phosphotriesters and alkyl cobalamins</title><title>Journal of the American Society for Mass Spectrometry</title><addtitle>J Am Soc Mass Spectrom</addtitle><description>DNA-phosphate adducts are known to be formed by a variety of alkylating agents. Due to little or no repair of DNA-phosphate adducts, these adducts may offer increased possibilities of both identifying and quantifying DNA adducts. The formation of DNA-phosphate adducts leads to a complete esterification of the phosphate group giving rise to a phosphotriester configuration. This work consists of the characterization of ethyl phosphotriesters (Ethyl PTE) using miniaturized LC-ESI-MS/MS and column switching in enzymatic hydrolysate of DNA treated in vitro with the model compound
N-ethyl-
N-nitrosourea (ENU). In vitro ENU-treated DNA was enzymatically degraded using nuclease P1, phosphodiesterase, and alkaline phosphatase. The use of column switch allowed for large-volume injections, where unmodified nucleosides were discarded in the loading step. The analytes were forward flushed to the analytical column in the eluting step and separated using a linear gradient. Ten different ethyl PTEs (dGpEtdG, dApEtdA, dCpEtdC, TpEtT, dGpEtdA, dGpEtdC, dGpEtT, dApEtdC, dApEtT, and dCpEtT) were characterized by their masses and CAD product ion spectra. Measurements of accurate masses were carried out yielding experimental masses within 5 ppm of the calculated masses for 9 of the 10 ethyl PTEs. For comparison, the enzymatic hydrolysate of ENU-treated DNA was subjected to transalkylation of the DNA-phosphate adducts by cob(I)alamin. Formed ethyl-cobalamins were analyzed according to earlier developed methods. The limit of detection of an alkyl-cobalamin standard and an alkyl PTE standard was 2 fmol and 5 fmol, respectively.</description><subject>Adducts</subject><subject>Alkaline phosphatase</subject><subject>Alkylation</subject><subject>Analytical biochemistry: general aspects, technics, instrumentation</subject><subject>Analytical, structural and metabolic biochemistry</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cattle</subject><subject>Deoxyribonucleic acid</subject><subject>DNA</subject><subject>DNA Adducts - analysis</subject><subject>DNA Adducts - chemistry</subject><subject>Esterification</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Isomerism</subject><subject>Mass spectrometry</subject><subject>Mass Spectrometry - instrumentation</subject><subject>Mass Spectrometry - methods</subject><subject>Molecular Structure</subject><subject>Nuclease</subject><subject>Phosphates - analysis</subject><subject>Reproducibility of Results</subject><subject>Sensitivity and Specificity</subject><subject>Spectrometry, Mass, Electrospray Ionization</subject><subject>Switching</subject><subject>Thymus Gland</subject><subject>Transalkylation</subject><subject>Vitamin B 12 - analysis</subject><subject>Vitamin B 12 - chemistry</subject><issn>1044-0305</issn><issn>1879-1123</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>8G5</sourceid><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>GNUQQ</sourceid><sourceid>GUQSH</sourceid><sourceid>M2O</sourceid><recordid>eNp90c-K1TAUBvAiivNHn0CQgOiunZw0bVrBxTA4Kgy40XVIk9SbmibXnHbk-gA-t7n2guLCVbL4nY_D-YriGdAKKLRXUzUpnLFilNYVsIoCe1CcQyf6EoDVD_Ofcl7SmjZnxQXiRCkI2ovHxRk0lAva8vPi53VQ_oAOSRyJCarc7yLud2qxRBmz6gWJC-TeLSmSFV34QmYXnFrW5H5YQ7wuLbpyxqsZiQqG6OjXORD87ha9y_w12QLjkpzFxaaNKf_14DMelFc5EJ8Uj0bl0T49vZfF59u3n27el3cf3324ub4rNW-6peS9siMzVDedoaK2o2CUQ6d10w49A20YcGZ1a7QZqBqg1kCFokYMDedWsPqyeLXl7lP8tuaF5OxQW-9VsHFFKUAI6FuR4Yt_4BTXlG-FEvqG8Yb3_VHVm9IpIiY7yn1ys0oHCVQeS5KT_F2SPJYkgclcUp56fspeh9maPzOnVjJ4eQIKtfJjUkE7_Mu1rOV9l92bzdl8sntnk0TtbNDWuGT1Ik10_13kF36-sz8</recordid><startdate>20040401</startdate><enddate>20040401</enddate><creator>Haglund, Johanna</creator><creator>Van Dongen, Walter</creator><creator>Lemière, Filip</creator><creator>Esmans, Eddy L</creator><general>Elsevier Inc</general><general>Elsevier Science</general><general>Springer Nature B.V</general><scope>6I.</scope><scope>AAFTH</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>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FE</scope><scope>8FG</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>ARAPS</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>M2O</scope><scope>MBDVC</scope><scope>P5Z</scope><scope>P62</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope></search><sort><creationdate>20040401</creationdate><title>Analysis of dna-phosphate adducts in vitro using miniaturized lc-esi-ms/ms and column switching: phosphotriesters and alkyl cobalamins</title><author>Haglund, Johanna ; Van Dongen, Walter ; Lemière, Filip ; Esmans, Eddy L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c458t-49aef2d0c58d073ef720418cc56b921cd2142ec6dcdb0ab13c107a0d7b544e723</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Adducts</topic><topic>Alkaline phosphatase</topic><topic>Alkylation</topic><topic>Analytical biochemistry: general aspects, technics, instrumentation</topic><topic>Analytical, structural and metabolic biochemistry</topic><topic>Animals</topic><topic>Biological and medical sciences</topic><topic>Cattle</topic><topic>Deoxyribonucleic acid</topic><topic>DNA</topic><topic>DNA Adducts - analysis</topic><topic>DNA Adducts - chemistry</topic><topic>Esterification</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Isomerism</topic><topic>Mass spectrometry</topic><topic>Mass Spectrometry - instrumentation</topic><topic>Mass Spectrometry - methods</topic><topic>Molecular Structure</topic><topic>Nuclease</topic><topic>Phosphates - analysis</topic><topic>Reproducibility of Results</topic><topic>Sensitivity and Specificity</topic><topic>Spectrometry, Mass, Electrospray Ionization</topic><topic>Switching</topic><topic>Thymus Gland</topic><topic>Transalkylation</topic><topic>Vitamin B 12 - analysis</topic><topic>Vitamin B 12 - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Haglund, Johanna</creatorcontrib><creatorcontrib>Van Dongen, Walter</creatorcontrib><creatorcontrib>Lemière, Filip</creatorcontrib><creatorcontrib>Esmans, Eddy L</creatorcontrib><collection>ScienceDirect Open Access Titles</collection><collection>Elsevier:ScienceDirect:Open Access</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>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>Advanced Technologies & Aerospace Collection</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Research Library</collection><collection>Research Library (Corporate)</collection><collection>Advanced Technologies & Aerospace Database</collection><collection>ProQuest Advanced Technologies & Aerospace Collection</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Society for Mass Spectrometry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Haglund, Johanna</au><au>Van Dongen, Walter</au><au>Lemière, Filip</au><au>Esmans, Eddy L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Analysis of dna-phosphate adducts in vitro using miniaturized lc-esi-ms/ms and column switching: phosphotriesters and alkyl cobalamins</atitle><jtitle>Journal of the American Society for Mass Spectrometry</jtitle><addtitle>J Am Soc Mass Spectrom</addtitle><date>2004-04-01</date><risdate>2004</risdate><volume>15</volume><issue>4</issue><spage>593</spage><epage>606</epage><pages>593-606</pages><issn>1044-0305</issn><eissn>1879-1123</eissn><abstract>DNA-phosphate adducts are known to be formed by a variety of alkylating agents. Due to little or no repair of DNA-phosphate adducts, these adducts may offer increased possibilities of both identifying and quantifying DNA adducts. The formation of DNA-phosphate adducts leads to a complete esterification of the phosphate group giving rise to a phosphotriester configuration. This work consists of the characterization of ethyl phosphotriesters (Ethyl PTE) using miniaturized LC-ESI-MS/MS and column switching in enzymatic hydrolysate of DNA treated in vitro with the model compound
N-ethyl-
N-nitrosourea (ENU). In vitro ENU-treated DNA was enzymatically degraded using nuclease P1, phosphodiesterase, and alkaline phosphatase. The use of column switch allowed for large-volume injections, where unmodified nucleosides were discarded in the loading step. The analytes were forward flushed to the analytical column in the eluting step and separated using a linear gradient. Ten different ethyl PTEs (dGpEtdG, dApEtdA, dCpEtdC, TpEtT, dGpEtdA, dGpEtdC, dGpEtT, dApEtdC, dApEtT, and dCpEtT) were characterized by their masses and CAD product ion spectra. Measurements of accurate masses were carried out yielding experimental masses within 5 ppm of the calculated masses for 9 of the 10 ethyl PTEs. For comparison, the enzymatic hydrolysate of ENU-treated DNA was subjected to transalkylation of the DNA-phosphate adducts by cob(I)alamin. Formed ethyl-cobalamins were analyzed according to earlier developed methods. The limit of detection of an alkyl-cobalamin standard and an alkyl PTE standard was 2 fmol and 5 fmol, respectively.</abstract><cop>New York, NY</cop><pub>Elsevier Inc</pub><pmid>15047064</pmid><doi>10.1016/j.jasms.2003.12.012</doi><tpages>14</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Adducts Alkaline phosphatase Alkylation Analytical biochemistry: general aspects, technics, instrumentation Analytical, structural and metabolic biochemistry Animals Biological and medical sciences Cattle Deoxyribonucleic acid DNA DNA Adducts - analysis DNA Adducts - chemistry Esterification Fundamental and applied biological sciences. Psychology Isomerism Mass spectrometry Mass Spectrometry - instrumentation Mass Spectrometry - methods Molecular Structure Nuclease Phosphates - analysis Reproducibility of Results Sensitivity and Specificity Spectrometry, Mass, Electrospray Ionization Switching Thymus Gland Transalkylation Vitamin B 12 - analysis Vitamin B 12 - chemistry |
| title | Analysis of dna-phosphate adducts in vitro using miniaturized lc-esi-ms/ms and column switching: phosphotriesters and alkyl cobalamins |
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