Identification of Epoxide Functionalities in Protonated Monofunctional Analytes by Using Ion/Molecule Reactions and Collision-Activated Dissociation in Different Ion Trap Tandem Mass Spectrometers
A mass spectrometric method has been delineated for the identification of the epoxide functionalities in unknown monofunctional analytes. This method utilizes gas-phase ion/molecule reactions of protonated analytes with neutral trimethyl borate (TMB) followed by collision-activated dissociation (CAD...
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| Veröffentlicht in: | Journal of the American Society for Mass Spectrometry 2012-01, Vol.23 (1), p.12-22 |
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| creator | Eismin, Ryan J. Fu, Mingkun Yem, Sonoeun Widjaja, Fanny Kenttämaa, Hilkka I. |
| description | A mass spectrometric method has been delineated for the identification of the epoxide functionalities in unknown monofunctional analytes. This method utilizes gas-phase ion/molecule reactions of protonated analytes with neutral trimethyl borate (TMB) followed by collision-activated dissociation (CAD) in an ion trapping mass spectrometer (tested for a Fourier-transform ion cyclotron resonance and a linear quadrupole ion trap). The ion/molecule reaction involves proton transfer from the protonated analyte to TMB, followed by addition of the analyte to TMB and elimination of methanol. Based on literature, this reaction allows the general identification of oxygen-containing analytes. Vinyl and phenyl epoxides can be differentiated from other oxygen-containing analytes, including other epoxides, based on the loss of a second methanol molecule upon CAD of the addition/methanol elimination product. The only other analytes found to undergo this elimination are some amides but they also lose O = B-R (R = group bound to carbonyl), which allows their identification. On the other hand, other epoxides can be differentiated from vinyl and phenyl epoxides and from other monofunctional analytes based on the loss of (CH
3
O)
2
BOH or formation of protonated (CH
3
O)
2
BOH upon CAD of the addition/methanol elimination product. For propylene oxide and 2,3-dimethyloxirane, the (CH
3
O)
2
BOH fragment is more basic than the hydrocarbon fragment, and the diagnostic ion (CH
3
O)
2
BOH
2
+
is formed. These reactions involve opening of the epoxide ring. The only other analytes found to undergo (CH
3
O)
2
BOH elimination are carboxylic acids, but they can be differentiated from the rest based on several published ion/molecule reaction methods. Similar results were obtained in the Fourier-transform ion cyclotron resonance and linear quadrupole ion trap mass spectrometer. |
| doi_str_mv | 10.1007/s13361-011-0249-y |
| format | Article |
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3
O)
2
BOH or formation of protonated (CH
3
O)
2
BOH upon CAD of the addition/methanol elimination product. For propylene oxide and 2,3-dimethyloxirane, the (CH
3
O)
2
BOH fragment is more basic than the hydrocarbon fragment, and the diagnostic ion (CH
3
O)
2
BOH
2
+
is formed. These reactions involve opening of the epoxide ring. The only other analytes found to undergo (CH
3
O)
2
BOH elimination are carboxylic acids, but they can be differentiated from the rest based on several published ion/molecule reaction methods. Similar results were obtained in the Fourier-transform ion cyclotron resonance and linear quadrupole ion trap mass spectrometer.</description><identifier>ISSN: 1044-0305</identifier><identifier>EISSN: 1879-1123</identifier><identifier>DOI: 10.1007/s13361-011-0249-y</identifier><identifier>PMID: 22002227</identifier><language>eng</language><publisher>New York: Springer-Verlag</publisher><subject>Amides ; Analytical Chemistry ; Basic oxides ; Bioinformatics ; Biotechnology ; Borates - chemistry ; Carbonyls ; Carboxylic acids ; Cascade chemical reactions ; catalysis (homogeneous), catalysis (heterogeneous), biofuels (including algae and biomass), bio-inspired, materials and chemistry by design, synthesis (self-assembly), synthesis (scalable processing) ; Chemistry ; Chemistry and Materials Science ; Cyclotron resonance ; Diagnostic systems ; Epoxy Compounds - chemistry ; Ethyl Ethers - chemistry ; Exact sciences and technology ; Fourier Analysis ; Identification ; Ions ; Ions - chemistry ; Mass spectrometers ; Mass spectrometry ; Methanol ; Methanol - chemistry ; Organic Chemistry ; Oxygen - chemistry ; Propylene ; Propylene oxide ; Proteomics ; Protons ; Quadrupoles ; Reactivity and mechanisms ; Research Article ; Spectrometers ; Spectrometry ; Tandem Mass Spectrometry - instrumentation ; Tandem Mass Spectrometry - methods</subject><ispartof>Journal of the American Society for Mass Spectrometry, 2012-01, Vol.23 (1), p.12-22</ispartof><rights>American Society for Mass Spectrometry 2011</rights><rights>2015 INIST-CNRS</rights><rights>American Society for Mass Spectrometry, 2011</rights><rights>Journal of The American Society for Mass Spectrometry is a copyright of Springer, 2012.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c471t-51133df764e2564da288bd72ce2ceca29474135d7ea4ca26c958237d3d5d50963</citedby><cites>FETCH-LOGICAL-c471t-51133df764e2564da288bd72ce2ceca29474135d7ea4ca26c958237d3d5d50963</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s13361-011-0249-y$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s13361-011-0249-y$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,885,27924,27925,41488,42557,51319</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25556379$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22002227$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/1066744$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Eismin, Ryan J.</creatorcontrib><creatorcontrib>Fu, Mingkun</creatorcontrib><creatorcontrib>Yem, Sonoeun</creatorcontrib><creatorcontrib>Widjaja, Fanny</creatorcontrib><creatorcontrib>Kenttämaa, Hilkka I.</creatorcontrib><creatorcontrib>Energy Frontier Research Centers (EFRC)</creatorcontrib><creatorcontrib>Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio)</creatorcontrib><title>Identification of Epoxide Functionalities in Protonated Monofunctional Analytes by Using Ion/Molecule Reactions and Collision-Activated Dissociation in Different Ion Trap Tandem Mass Spectrometers</title><title>Journal of the American Society for Mass Spectrometry</title><addtitle>J. Am. Soc. Mass Spectrom</addtitle><addtitle>J Am Soc Mass Spectrom</addtitle><description>A mass spectrometric method has been delineated for the identification of the epoxide functionalities in unknown monofunctional analytes. This method utilizes gas-phase ion/molecule reactions of protonated analytes with neutral trimethyl borate (TMB) followed by collision-activated dissociation (CAD) in an ion trapping mass spectrometer (tested for a Fourier-transform ion cyclotron resonance and a linear quadrupole ion trap). The ion/molecule reaction involves proton transfer from the protonated analyte to TMB, followed by addition of the analyte to TMB and elimination of methanol. Based on literature, this reaction allows the general identification of oxygen-containing analytes. Vinyl and phenyl epoxides can be differentiated from other oxygen-containing analytes, including other epoxides, based on the loss of a second methanol molecule upon CAD of the addition/methanol elimination product. The only other analytes found to undergo this elimination are some amides but they also lose O = B-R (R = group bound to carbonyl), which allows their identification. On the other hand, other epoxides can be differentiated from vinyl and phenyl epoxides and from other monofunctional analytes based on the loss of (CH
3
O)
2
BOH or formation of protonated (CH
3
O)
2
BOH upon CAD of the addition/methanol elimination product. For propylene oxide and 2,3-dimethyloxirane, the (CH
3
O)
2
BOH fragment is more basic than the hydrocarbon fragment, and the diagnostic ion (CH
3
O)
2
BOH
2
+
is formed. These reactions involve opening of the epoxide ring. The only other analytes found to undergo (CH
3
O)
2
BOH elimination are carboxylic acids, but they can be differentiated from the rest based on several published ion/molecule reaction methods. Similar results were obtained in the Fourier-transform ion cyclotron resonance and linear quadrupole ion trap mass spectrometer.</description><subject>Amides</subject><subject>Analytical Chemistry</subject><subject>Basic oxides</subject><subject>Bioinformatics</subject><subject>Biotechnology</subject><subject>Borates - chemistry</subject><subject>Carbonyls</subject><subject>Carboxylic acids</subject><subject>Cascade chemical reactions</subject><subject>catalysis (homogeneous), catalysis (heterogeneous), biofuels (including algae and biomass), bio-inspired, materials and chemistry by design, synthesis (self-assembly), synthesis (scalable processing)</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Cyclotron resonance</subject><subject>Diagnostic systems</subject><subject>Epoxy Compounds - chemistry</subject><subject>Ethyl Ethers - chemistry</subject><subject>Exact sciences and technology</subject><subject>Fourier Analysis</subject><subject>Identification</subject><subject>Ions</subject><subject>Ions - chemistry</subject><subject>Mass spectrometers</subject><subject>Mass spectrometry</subject><subject>Methanol</subject><subject>Methanol - chemistry</subject><subject>Organic Chemistry</subject><subject>Oxygen - chemistry</subject><subject>Propylene</subject><subject>Propylene oxide</subject><subject>Proteomics</subject><subject>Protons</subject><subject>Quadrupoles</subject><subject>Reactivity and mechanisms</subject><subject>Research Article</subject><subject>Spectrometers</subject><subject>Spectrometry</subject><subject>Tandem Mass Spectrometry - instrumentation</subject><subject>Tandem Mass Spectrometry - methods</subject><issn>1044-0305</issn><issn>1879-1123</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</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>eNp1ks1uEzEQx1cIREvhAbggC4Q4LbW99jp7jNIWIrUCQXq2HNtbXG3s1ONF5P14MCbdUBASkr9m_Jv_jOypqpeMvmeUqlNgTdOymjKcXHT17lF1zGaqqxnjzWM8UyFq2lB5VD0DuKWUKdqpp9UR55RyztVx9XPpfCyhD9aUkCJJPTnfph_BeXIxRrv3mSGU4IGESD7nVNBRvCNXKab-gSBzXHYFqfWOXEOIN2SZ4ulVGrwdB0--eHNPAjHRkUUahgBo1nP0fr_XOwsAyYapCkx1FvreZ6xtL0RW2WzJCmP9hlwZAPJ1623JaeOLz_C8etKbAfyLw35SXV-crxYf68tPH5aL-WVthWKllgzfy_WqFZ7LVjjDZ7O1U9x6HNbwTijBGumUNwLN1nZyxhvlGiedpF3bnFSvJ90EJWiwoXj7zaYYsRbNaNsqIRB6N0HbnO5GD0VvAlg_DCb6NILuGBcNbWd7uTf_kLdpzPiQoFknGcXsXCLFJsrmBJB9r7c5bEzeYUa9bwM9tYHGNtD7NtA7jHl1UB7XG-8eIn7_OwJvD4ABa4Y-m2gD_OGklG2jOuT4xAFexRuf_yrxv9l_ARXJzbk</recordid><startdate>20120101</startdate><enddate>20120101</enddate><creator>Eismin, Ryan J.</creator><creator>Fu, Mingkun</creator><creator>Yem, Sonoeun</creator><creator>Widjaja, Fanny</creator><creator>Kenttämaa, Hilkka I.</creator><general>Springer-Verlag</general><general>Elsevier</general><general>Springer Nature B.V</general><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><scope>OTOTI</scope></search><sort><creationdate>20120101</creationdate><title>Identification of Epoxide Functionalities in Protonated Monofunctional Analytes by Using Ion/Molecule Reactions and Collision-Activated Dissociation in Different Ion Trap Tandem Mass Spectrometers</title><author>Eismin, Ryan J. ; Fu, Mingkun ; Yem, Sonoeun ; Widjaja, Fanny ; Kenttämaa, Hilkka I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c471t-51133df764e2564da288bd72ce2ceca29474135d7ea4ca26c958237d3d5d50963</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Amides</topic><topic>Analytical Chemistry</topic><topic>Basic oxides</topic><topic>Bioinformatics</topic><topic>Biotechnology</topic><topic>Borates - chemistry</topic><topic>Carbonyls</topic><topic>Carboxylic acids</topic><topic>Cascade chemical reactions</topic><topic>catalysis (homogeneous), catalysis (heterogeneous), biofuels (including algae and biomass), bio-inspired, materials and chemistry by design, synthesis (self-assembly), synthesis (scalable processing)</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Cyclotron resonance</topic><topic>Diagnostic systems</topic><topic>Epoxy Compounds - chemistry</topic><topic>Ethyl Ethers - chemistry</topic><topic>Exact sciences and technology</topic><topic>Fourier Analysis</topic><topic>Identification</topic><topic>Ions</topic><topic>Ions - chemistry</topic><topic>Mass spectrometers</topic><topic>Mass spectrometry</topic><topic>Methanol</topic><topic>Methanol - chemistry</topic><topic>Organic Chemistry</topic><topic>Oxygen - chemistry</topic><topic>Propylene</topic><topic>Propylene oxide</topic><topic>Proteomics</topic><topic>Protons</topic><topic>Quadrupoles</topic><topic>Reactivity and mechanisms</topic><topic>Research Article</topic><topic>Spectrometers</topic><topic>Spectrometry</topic><topic>Tandem Mass Spectrometry - instrumentation</topic><topic>Tandem Mass Spectrometry - methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Eismin, Ryan J.</creatorcontrib><creatorcontrib>Fu, Mingkun</creatorcontrib><creatorcontrib>Yem, Sonoeun</creatorcontrib><creatorcontrib>Widjaja, Fanny</creatorcontrib><creatorcontrib>Kenttämaa, Hilkka I.</creatorcontrib><creatorcontrib>Energy Frontier Research Centers (EFRC)</creatorcontrib><creatorcontrib>Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio)</creatorcontrib><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><collection>OSTI.GOV</collection><jtitle>Journal of the American Society for Mass Spectrometry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Eismin, Ryan J.</au><au>Fu, Mingkun</au><au>Yem, Sonoeun</au><au>Widjaja, Fanny</au><au>Kenttämaa, Hilkka I.</au><aucorp>Energy Frontier Research Centers (EFRC)</aucorp><aucorp>Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio)</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Identification of Epoxide Functionalities in Protonated Monofunctional Analytes by Using Ion/Molecule Reactions and Collision-Activated Dissociation in Different Ion Trap Tandem Mass Spectrometers</atitle><jtitle>Journal of the American Society for Mass Spectrometry</jtitle><stitle>J. Am. Soc. Mass Spectrom</stitle><addtitle>J Am Soc Mass Spectrom</addtitle><date>2012-01-01</date><risdate>2012</risdate><volume>23</volume><issue>1</issue><spage>12</spage><epage>22</epage><pages>12-22</pages><issn>1044-0305</issn><eissn>1879-1123</eissn><abstract>A mass spectrometric method has been delineated for the identification of the epoxide functionalities in unknown monofunctional analytes. This method utilizes gas-phase ion/molecule reactions of protonated analytes with neutral trimethyl borate (TMB) followed by collision-activated dissociation (CAD) in an ion trapping mass spectrometer (tested for a Fourier-transform ion cyclotron resonance and a linear quadrupole ion trap). The ion/molecule reaction involves proton transfer from the protonated analyte to TMB, followed by addition of the analyte to TMB and elimination of methanol. Based on literature, this reaction allows the general identification of oxygen-containing analytes. Vinyl and phenyl epoxides can be differentiated from other oxygen-containing analytes, including other epoxides, based on the loss of a second methanol molecule upon CAD of the addition/methanol elimination product. The only other analytes found to undergo this elimination are some amides but they also lose O = B-R (R = group bound to carbonyl), which allows their identification. On the other hand, other epoxides can be differentiated from vinyl and phenyl epoxides and from other monofunctional analytes based on the loss of (CH
3
O)
2
BOH or formation of protonated (CH
3
O)
2
BOH upon CAD of the addition/methanol elimination product. For propylene oxide and 2,3-dimethyloxirane, the (CH
3
O)
2
BOH fragment is more basic than the hydrocarbon fragment, and the diagnostic ion (CH
3
O)
2
BOH
2
+
is formed. These reactions involve opening of the epoxide ring. The only other analytes found to undergo (CH
3
O)
2
BOH elimination are carboxylic acids, but they can be differentiated from the rest based on several published ion/molecule reaction methods. Similar results were obtained in the Fourier-transform ion cyclotron resonance and linear quadrupole ion trap mass spectrometer.</abstract><cop>New York</cop><pub>Springer-Verlag</pub><pmid>22002227</pmid><doi>10.1007/s13361-011-0249-y</doi><tpages>11</tpages><oa>free_for_read</oa></addata></record> |
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| identifier | ISSN: 1044-0305 |
| ispartof | Journal of the American Society for Mass Spectrometry, 2012-01, Vol.23 (1), p.12-22 |
| issn | 1044-0305 1879-1123 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_912430686 |
| source | MEDLINE; SpringerNature Journals |
| subjects | Amides Analytical Chemistry Basic oxides Bioinformatics Biotechnology Borates - chemistry Carbonyls Carboxylic acids Cascade chemical reactions catalysis (homogeneous), catalysis (heterogeneous), biofuels (including algae and biomass), bio-inspired, materials and chemistry by design, synthesis (self-assembly), synthesis (scalable processing) Chemistry Chemistry and Materials Science Cyclotron resonance Diagnostic systems Epoxy Compounds - chemistry Ethyl Ethers - chemistry Exact sciences and technology Fourier Analysis Identification Ions Ions - chemistry Mass spectrometers Mass spectrometry Methanol Methanol - chemistry Organic Chemistry Oxygen - chemistry Propylene Propylene oxide Proteomics Protons Quadrupoles Reactivity and mechanisms Research Article Spectrometers Spectrometry Tandem Mass Spectrometry - instrumentation Tandem Mass Spectrometry - methods |
| title | Identification of Epoxide Functionalities in Protonated Monofunctional Analytes by Using Ion/Molecule Reactions and Collision-Activated Dissociation in Different Ion Trap Tandem Mass Spectrometers |
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