Straightforward Synthesis of Deuterated Precursors To Demonstrate the Biogenesis of Aromatic Thiols In Wine
Straightforward synthesis of labeled S-3-(hexan-1-ol)-glutathione and S-4-(4-methylpentan-2-one)-glutathione has been developed through a conjugate addition optimization study. Sauvignon blanc fermentation experiments with the [2H10] S-4-(4-methylpentan-2-one)-glutathione used as a tracer released t...
Gespeichert in:
| Veröffentlicht in: | Journal of agricultural and food chemistry 2010-10, Vol.58 (19), p.10684-10689 |
|---|---|
| Hauptverfasser: | , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 10689 |
|---|---|
| container_issue | 19 |
| container_start_page | 10684 |
| container_title | Journal of agricultural and food chemistry |
| container_volume | 58 |
| creator | Roland, Aurélie Schneider, Rémi Razungles, Alain Le Guernevé, Christine Cavelier, Florine |
| description | Straightforward synthesis of labeled S-3-(hexan-1-ol)-glutathione and S-4-(4-methylpentan-2-one)-glutathione has been developed through a conjugate addition optimization study. Sauvignon blanc fermentation experiments with the [2H10] S-4-(4-methylpentan-2-one)-glutathione used as a tracer released the corresponding deuterated thiol, thus proving the direct relationship with the 4-mercapto-4-methylpentan-2-one under enological conditions. The conversion yield of such transformation was estimated to be close to 0.3%, opening an avenue for additional study on varietal thiol biogenesis. |
| doi_str_mv | 10.1021/jf101996p |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_758133571</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>758133571</sourcerecordid><originalsourceid>FETCH-LOGICAL-a368t-c7a7082c712d048cc9685cb002f5119dcec250b1c33681715717bf31ee66ab4f3</originalsourceid><addsrcrecordid>eNpt0MFu1DAQBmALUdGlcOAFwBeEOAQ8dh07x1KgrVQJpN2KY-Q49q6XJN56HKG-Pa522156msN8M5r5CXkH7AswDl-3Hhg0Tb17QRYgOaskgH5JFqw0Ky1rOCavEbeMMS0Ve0WOOdNcQgML8neZkwnrTfYx_TOpp8u7KW8cBqTR0-9uzi6Z7Hr6Ozk7J4wJ6SqWxhgnzPctWjj9FuLaTQ9jZymOJgdLV5sQB6RXE_0TJveGHHkzoHt7qCfk5ueP1flldf3r4ur87Loyota5ssqocp9VwHt2qq1tai1tV57x5a-mt85yyTqwonBQIBWozgtwrq5Nd-rFCfm037tL8XZ2mNsxoHXDYCYXZ2yV1CBEGSvy817aFBGT8-0uhdGkuxZYex9t-xhtse8PW-dudP2jfMiygI8HYNCawScz2YBPTgguhVDFfdg7b2Jr1qmYmyVnIBjopuaCPW0yFtttnNNU4nrmpP8bmZYy</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>758133571</pqid></control><display><type>article</type><title>Straightforward Synthesis of Deuterated Precursors To Demonstrate the Biogenesis of Aromatic Thiols In Wine</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Roland, Aurélie ; Schneider, Rémi ; Razungles, Alain ; Le Guernevé, Christine ; Cavelier, Florine</creator><creatorcontrib>Roland, Aurélie ; Schneider, Rémi ; Razungles, Alain ; Le Guernevé, Christine ; Cavelier, Florine</creatorcontrib><description>Straightforward synthesis of labeled S-3-(hexan-1-ol)-glutathione and S-4-(4-methylpentan-2-one)-glutathione has been developed through a conjugate addition optimization study. Sauvignon blanc fermentation experiments with the [2H10] S-4-(4-methylpentan-2-one)-glutathione used as a tracer released the corresponding deuterated thiol, thus proving the direct relationship with the 4-mercapto-4-methylpentan-2-one under enological conditions. The conversion yield of such transformation was estimated to be close to 0.3%, opening an avenue for additional study on varietal thiol biogenesis.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf101996p</identifier><identifier>PMID: 20825191</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>aromatic compounds ; biochemical pathways ; Biological and medical sciences ; biosynthesis ; Deuterium ; Fermentation ; Fermented food industries ; Food Chemistry/Biochemistry ; food composition ; Food industries ; Fruit - chemistry ; Fruit and vegetable industries ; Fundamental and applied biological sciences. Psychology ; glutathione ; Glutathione - analogs & derivatives ; Glutathione - biosynthesis ; Odorants - analysis ; optimization ; Sulfhydryl Compounds - metabolism ; thiols ; Vitis - chemistry ; white wines ; Wine - analysis ; winemaking ; Wines and vinegars</subject><ispartof>Journal of agricultural and food chemistry, 2010-10, Vol.58 (19), p.10684-10689</ispartof><rights>Copyright © 2010 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a368t-c7a7082c712d048cc9685cb002f5119dcec250b1c33681715717bf31ee66ab4f3</citedby><cites>FETCH-LOGICAL-a368t-c7a7082c712d048cc9685cb002f5119dcec250b1c33681715717bf31ee66ab4f3</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/jf101996p$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf101996p$$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=23325337$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20825191$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Roland, Aurélie</creatorcontrib><creatorcontrib>Schneider, Rémi</creatorcontrib><creatorcontrib>Razungles, Alain</creatorcontrib><creatorcontrib>Le Guernevé, Christine</creatorcontrib><creatorcontrib>Cavelier, Florine</creatorcontrib><title>Straightforward Synthesis of Deuterated Precursors To Demonstrate the Biogenesis of Aromatic Thiols In Wine</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>Straightforward synthesis of labeled S-3-(hexan-1-ol)-glutathione and S-4-(4-methylpentan-2-one)-glutathione has been developed through a conjugate addition optimization study. Sauvignon blanc fermentation experiments with the [2H10] S-4-(4-methylpentan-2-one)-glutathione used as a tracer released the corresponding deuterated thiol, thus proving the direct relationship with the 4-mercapto-4-methylpentan-2-one under enological conditions. The conversion yield of such transformation was estimated to be close to 0.3%, opening an avenue for additional study on varietal thiol biogenesis.</description><subject>aromatic compounds</subject><subject>biochemical pathways</subject><subject>Biological and medical sciences</subject><subject>biosynthesis</subject><subject>Deuterium</subject><subject>Fermentation</subject><subject>Fermented food industries</subject><subject>Food Chemistry/Biochemistry</subject><subject>food composition</subject><subject>Food industries</subject><subject>Fruit - chemistry</subject><subject>Fruit and vegetable industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>glutathione</subject><subject>Glutathione - analogs & derivatives</subject><subject>Glutathione - biosynthesis</subject><subject>Odorants - analysis</subject><subject>optimization</subject><subject>Sulfhydryl Compounds - metabolism</subject><subject>thiols</subject><subject>Vitis - chemistry</subject><subject>white wines</subject><subject>Wine - analysis</subject><subject>winemaking</subject><subject>Wines and vinegars</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0MFu1DAQBmALUdGlcOAFwBeEOAQ8dh07x1KgrVQJpN2KY-Q49q6XJN56HKG-Pa522156msN8M5r5CXkH7AswDl-3Hhg0Tb17QRYgOaskgH5JFqw0Ky1rOCavEbeMMS0Ve0WOOdNcQgML8neZkwnrTfYx_TOpp8u7KW8cBqTR0-9uzi6Z7Hr6Ozk7J4wJ6SqWxhgnzPctWjj9FuLaTQ9jZymOJgdLV5sQB6RXE_0TJveGHHkzoHt7qCfk5ueP1flldf3r4ur87Loyota5ssqocp9VwHt2qq1tai1tV57x5a-mt85yyTqwonBQIBWozgtwrq5Nd-rFCfm037tL8XZ2mNsxoHXDYCYXZ2yV1CBEGSvy817aFBGT8-0uhdGkuxZYex9t-xhtse8PW-dudP2jfMiygI8HYNCawScz2YBPTgguhVDFfdg7b2Jr1qmYmyVnIBjopuaCPW0yFtttnNNU4nrmpP8bmZYy</recordid><startdate>20101013</startdate><enddate>20101013</enddate><creator>Roland, Aurélie</creator><creator>Schneider, Rémi</creator><creator>Razungles, Alain</creator><creator>Le Guernevé, Christine</creator><creator>Cavelier, Florine</creator><general>American Chemical Society</general><scope>FBQ</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>20101013</creationdate><title>Straightforward Synthesis of Deuterated Precursors To Demonstrate the Biogenesis of Aromatic Thiols In Wine</title><author>Roland, Aurélie ; Schneider, Rémi ; Razungles, Alain ; Le Guernevé, Christine ; Cavelier, Florine</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a368t-c7a7082c712d048cc9685cb002f5119dcec250b1c33681715717bf31ee66ab4f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>aromatic compounds</topic><topic>biochemical pathways</topic><topic>Biological and medical sciences</topic><topic>biosynthesis</topic><topic>Deuterium</topic><topic>Fermentation</topic><topic>Fermented food industries</topic><topic>Food Chemistry/Biochemistry</topic><topic>food composition</topic><topic>Food industries</topic><topic>Fruit - chemistry</topic><topic>Fruit and vegetable industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>glutathione</topic><topic>Glutathione - analogs & derivatives</topic><topic>Glutathione - biosynthesis</topic><topic>Odorants - analysis</topic><topic>optimization</topic><topic>Sulfhydryl Compounds - metabolism</topic><topic>thiols</topic><topic>Vitis - chemistry</topic><topic>white wines</topic><topic>Wine - analysis</topic><topic>winemaking</topic><topic>Wines and vinegars</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Roland, Aurélie</creatorcontrib><creatorcontrib>Schneider, Rémi</creatorcontrib><creatorcontrib>Razungles, Alain</creatorcontrib><creatorcontrib>Le Guernevé, Christine</creatorcontrib><creatorcontrib>Cavelier, Florine</creatorcontrib><collection>AGRIS</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>Roland, Aurélie</au><au>Schneider, Rémi</au><au>Razungles, Alain</au><au>Le Guernevé, Christine</au><au>Cavelier, Florine</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Straightforward Synthesis of Deuterated Precursors To Demonstrate the Biogenesis of Aromatic Thiols In Wine</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2010-10-13</date><risdate>2010</risdate><volume>58</volume><issue>19</issue><spage>10684</spage><epage>10689</epage><pages>10684-10689</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>Straightforward synthesis of labeled S-3-(hexan-1-ol)-glutathione and S-4-(4-methylpentan-2-one)-glutathione has been developed through a conjugate addition optimization study. Sauvignon blanc fermentation experiments with the [2H10] S-4-(4-methylpentan-2-one)-glutathione used as a tracer released the corresponding deuterated thiol, thus proving the direct relationship with the 4-mercapto-4-methylpentan-2-one under enological conditions. The conversion yield of such transformation was estimated to be close to 0.3%, opening an avenue for additional study on varietal thiol biogenesis.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>20825191</pmid><doi>10.1021/jf101996p</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0021-8561 |
| ispartof | Journal of agricultural and food chemistry, 2010-10, Vol.58 (19), p.10684-10689 |
| issn | 0021-8561 1520-5118 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_758133571 |
| source | MEDLINE; American Chemical Society Journals |
| subjects | aromatic compounds biochemical pathways Biological and medical sciences biosynthesis Deuterium Fermentation Fermented food industries Food Chemistry/Biochemistry food composition Food industries Fruit - chemistry Fruit and vegetable industries Fundamental and applied biological sciences. Psychology glutathione Glutathione - analogs & derivatives Glutathione - biosynthesis Odorants - analysis optimization Sulfhydryl Compounds - metabolism thiols Vitis - chemistry white wines Wine - analysis winemaking Wines and vinegars |
| title | Straightforward Synthesis of Deuterated Precursors To Demonstrate the Biogenesis of Aromatic Thiols In Wine |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-28T03%3A36%3A00IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Straightforward%20Synthesis%20of%20Deuterated%20Precursors%20To%20Demonstrate%20the%20Biogenesis%20of%20Aromatic%20Thiols%20In%20Wine&rft.jtitle=Journal%20of%20agricultural%20and%20food%20chemistry&rft.au=Roland,%20Aure%CC%81lie&rft.date=2010-10-13&rft.volume=58&rft.issue=19&rft.spage=10684&rft.epage=10689&rft.pages=10684-10689&rft.issn=0021-8561&rft.eissn=1520-5118&rft.coden=JAFCAU&rft_id=info:doi/10.1021/jf101996p&rft_dat=%3Cproquest_cross%3E758133571%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=758133571&rft_id=info:pmid/20825191&rfr_iscdi=true |