Fate and Kinetic Modeling of Reactivity of Alkanesulfenic Acids and Thiosulfinates in Model Systems and Onion Homogenates
The dynamic changes in thiosulfinate profiles were studied in reaction systems containing a crude onion alliinase, S-alk(en)yl-l-cysteine sulfoxide substrates (1) and preformed thiosulfinates (4). Regioisomeric excesses of one of two possible heterologous 4 species (RS(O)SR‘, where R ≠ R‘) could be...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2002-04, Vol.50 (9), p.2652-2659 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Shen, Cunxi Hong, Zongxuan Parkin, Kirk L |
| description | The dynamic changes in thiosulfinate profiles were studied in reaction systems containing a crude onion alliinase, S-alk(en)yl-l-cysteine sulfoxide substrates (1) and preformed thiosulfinates (4). Regioisomeric excesses of one of two possible heterologous 4 species (RS(O)SR‘, where R ≠ R‘) could be manipulated under conditions where alliinase, 1, and 4 levels were varied. Regioisomeric excesses could be explained by a thiosulfinate (4)/alkanesulfenic acid (2) trapping mechanism, with the greatest control over product profile governed by the rate of 2 generation in the system. The series of reactions existing in this dynamic reaction system was kinetically modeled with reasonable fits to the experimental data. The application of the 4/2 trapping strategy to manipulate thiosulfinate and related organosulfur product profiles in diluted onion homogenates was demonstrated using exogenous MeS(O)SMe (4a), PrS(O)SPr (4c), and AllS(O)SAll (4d) as the preformed thiosulfinate. Keywords: Thiosulfinate; alkanesulfenic acid; alliinase; kinetics; trapping; Allium |
| doi_str_mv | 10.1021/jf0110147 |
| format | Article |
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Regioisomeric excesses of one of two possible heterologous 4 species (RS(O)SR‘, where R ≠ R‘) could be manipulated under conditions where alliinase, 1, and 4 levels were varied. Regioisomeric excesses could be explained by a thiosulfinate (4)/alkanesulfenic acid (2) trapping mechanism, with the greatest control over product profile governed by the rate of 2 generation in the system. The series of reactions existing in this dynamic reaction system was kinetically modeled with reasonable fits to the experimental data. The application of the 4/2 trapping strategy to manipulate thiosulfinate and related organosulfur product profiles in diluted onion homogenates was demonstrated using exogenous MeS(O)SMe (4a), PrS(O)SPr (4c), and AllS(O)SAll (4d) as the preformed thiosulfinate. Keywords: Thiosulfinate; alkanesulfenic acid; alliinase; kinetics; trapping; Allium</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf0110147</identifier><identifier>PMID: 11958637</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Agronomy. Soil science and plant productions ; Alkanes - chemistry ; Alkanes - metabolism ; Allium - chemistry ; Biological and medical sciences ; Carbon-Sulfur Lyases - metabolism ; Economic plant physiology ; Fundamental and applied biological sciences. Psychology ; General pharmacology ; Kinetics ; Medical sciences ; Models, Chemical ; Nitrogen metabolism and other ones (excepting carbon metabolism) ; Nutrition. Photosynthesis. Respiration. Metabolism ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Sulfenic Acids - chemistry ; Sulfenic Acids - metabolism ; Sulfinic Acids - chemistry ; Sulfinic Acids - metabolism</subject><ispartof>Journal of agricultural and food chemistry, 2002-04, Vol.50 (9), p.2652-2659</ispartof><rights>Copyright © 2002 American Chemical Society</rights><rights>2002 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-e207ca8e54dec1cfc437a62bb23171449ba722120e3d4ce73b67540a3d5e317a3</citedby><cites>FETCH-LOGICAL-a379t-e207ca8e54dec1cfc437a62bb23171449ba722120e3d4ce73b67540a3d5e317a3</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/jf0110147$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf0110147$$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=13619449$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11958637$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Shen, Cunxi</creatorcontrib><creatorcontrib>Hong, Zongxuan</creatorcontrib><creatorcontrib>Parkin, Kirk L</creatorcontrib><title>Fate and Kinetic Modeling of Reactivity of Alkanesulfenic Acids and Thiosulfinates in Model Systems and Onion Homogenates</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The dynamic changes in thiosulfinate profiles were studied in reaction systems containing a crude onion alliinase, S-alk(en)yl-l-cysteine sulfoxide substrates (1) and preformed thiosulfinates (4). Regioisomeric excesses of one of two possible heterologous 4 species (RS(O)SR‘, where R ≠ R‘) could be manipulated under conditions where alliinase, 1, and 4 levels were varied. Regioisomeric excesses could be explained by a thiosulfinate (4)/alkanesulfenic acid (2) trapping mechanism, with the greatest control over product profile governed by the rate of 2 generation in the system. The series of reactions existing in this dynamic reaction system was kinetically modeled with reasonable fits to the experimental data. The application of the 4/2 trapping strategy to manipulate thiosulfinate and related organosulfur product profiles in diluted onion homogenates was demonstrated using exogenous MeS(O)SMe (4a), PrS(O)SPr (4c), and AllS(O)SAll (4d) as the preformed thiosulfinate. Keywords: Thiosulfinate; alkanesulfenic acid; alliinase; kinetics; trapping; Allium</description><subject>Agronomy. Soil science and plant productions</subject><subject>Alkanes - chemistry</subject><subject>Alkanes - metabolism</subject><subject>Allium - chemistry</subject><subject>Biological and medical sciences</subject><subject>Carbon-Sulfur Lyases - metabolism</subject><subject>Economic plant physiology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General pharmacology</subject><subject>Kinetics</subject><subject>Medical sciences</subject><subject>Models, Chemical</subject><subject>Nitrogen metabolism and other ones (excepting carbon metabolism)</subject><subject>Nutrition. Photosynthesis. Respiration. Metabolism</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>Sulfenic Acids - chemistry</subject><subject>Sulfenic Acids - metabolism</subject><subject>Sulfinic Acids - chemistry</subject><subject>Sulfinic Acids - metabolism</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0EFP2zAYBmALDUFhO-wPTLkwiUPAnx3H6bFigyJAoLXbjpbjfAGXxGZxMq3_HpdU9LKTZfvxq88vIZ-BngFlcL6qKQCFTO6RCQhGUwFQfCATGi_TQuRwSI5CWFFKCyHpATkEmIoi53JC1pe6x0S7KrmxDntrkjtfYWPdY-Lr5Adq09u_tl9vdrPmWTsMQ1Oji3BmbBXeni6frN8cWxfDQmLdGJIs1qHHdjT3znqXzH3rH_GNfST7tW4Cftqux-Tn5fflxTy9vb-6vpjdpprLaZ8io9LoAkVWoQFTm4xLnbOyZBwkZNm01JIxYBR5lRmUvMylyKjmlcAoND8mX8fcl87_GTD0qrXBYNPEv_ghKAl57IyJCE9HaDofQoe1eulsq7u1Aqo2Pav3nqP9sg0dyharndwWG8HJFuhgdFN32hkbdo7nMI3DR5eOzsaq_r3f6-5Z5ZJLoZYPC_Ww-PV7Mf-Wq2KXq01QKz90Lnb3nwFfAdmpoD0</recordid><startdate>20020424</startdate><enddate>20020424</enddate><creator>Shen, Cunxi</creator><creator>Hong, Zongxuan</creator><creator>Parkin, Kirk L</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>7X8</scope></search><sort><creationdate>20020424</creationdate><title>Fate and Kinetic Modeling of Reactivity of Alkanesulfenic Acids and Thiosulfinates in Model Systems and Onion Homogenates</title><author>Shen, Cunxi ; Hong, Zongxuan ; Parkin, Kirk L</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-e207ca8e54dec1cfc437a62bb23171449ba722120e3d4ce73b67540a3d5e317a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Agronomy. Soil science and plant productions</topic><topic>Alkanes - chemistry</topic><topic>Alkanes - metabolism</topic><topic>Allium - chemistry</topic><topic>Biological and medical sciences</topic><topic>Carbon-Sulfur Lyases - metabolism</topic><topic>Economic plant physiology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General pharmacology</topic><topic>Kinetics</topic><topic>Medical sciences</topic><topic>Models, Chemical</topic><topic>Nitrogen metabolism and other ones (excepting carbon metabolism)</topic><topic>Nutrition. Photosynthesis. Respiration. Metabolism</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>Sulfenic Acids - chemistry</topic><topic>Sulfenic Acids - metabolism</topic><topic>Sulfinic Acids - chemistry</topic><topic>Sulfinic Acids - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shen, Cunxi</creatorcontrib><creatorcontrib>Hong, Zongxuan</creatorcontrib><creatorcontrib>Parkin, Kirk L</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>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shen, Cunxi</au><au>Hong, Zongxuan</au><au>Parkin, Kirk L</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Fate and Kinetic Modeling of Reactivity of Alkanesulfenic Acids and Thiosulfinates in Model Systems and Onion Homogenates</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2002-04-24</date><risdate>2002</risdate><volume>50</volume><issue>9</issue><spage>2652</spage><epage>2659</epage><pages>2652-2659</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>The dynamic changes in thiosulfinate profiles were studied in reaction systems containing a crude onion alliinase, S-alk(en)yl-l-cysteine sulfoxide substrates (1) and preformed thiosulfinates (4). Regioisomeric excesses of one of two possible heterologous 4 species (RS(O)SR‘, where R ≠ R‘) could be manipulated under conditions where alliinase, 1, and 4 levels were varied. Regioisomeric excesses could be explained by a thiosulfinate (4)/alkanesulfenic acid (2) trapping mechanism, with the greatest control over product profile governed by the rate of 2 generation in the system. The series of reactions existing in this dynamic reaction system was kinetically modeled with reasonable fits to the experimental data. The application of the 4/2 trapping strategy to manipulate thiosulfinate and related organosulfur product profiles in diluted onion homogenates was demonstrated using exogenous MeS(O)SMe (4a), PrS(O)SPr (4c), and AllS(O)SAll (4d) as the preformed thiosulfinate. Keywords: Thiosulfinate; alkanesulfenic acid; alliinase; kinetics; trapping; Allium</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>11958637</pmid><doi>10.1021/jf0110147</doi><tpages>8</tpages></addata></record> |
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| subjects | Agronomy. Soil science and plant productions Alkanes - chemistry Alkanes - metabolism Allium - chemistry Biological and medical sciences Carbon-Sulfur Lyases - metabolism Economic plant physiology Fundamental and applied biological sciences. Psychology General pharmacology Kinetics Medical sciences Models, Chemical Nitrogen metabolism and other ones (excepting carbon metabolism) Nutrition. Photosynthesis. Respiration. Metabolism Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Sulfenic Acids - chemistry Sulfenic Acids - metabolism Sulfinic Acids - chemistry Sulfinic Acids - metabolism |
| title | Fate and Kinetic Modeling of Reactivity of Alkanesulfenic Acids and Thiosulfinates in Model Systems and Onion Homogenates |
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