Mechanisms of Alkylpyrazine Formation in a Potato Model System Containing Added Glycine
The use of glycine to limit acrylamide formation during the heating of a potato model system was also found to alter the relative proportions of alkylpyrazines. The addition of glycine increased the quantities of several alkylpyrazines, and labeling studies using [2-13C]glycine showed that those alk...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2007-05, Vol.55 (10), p.4087-4094 |
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| creator | Low, Mei Yin Parker, Jane K. Mottram, Donald S. |
| description | The use of glycine to limit acrylamide formation during the heating of a potato model system was also found to alter the relative proportions of alkylpyrazines. The addition of glycine increased the quantities of several alkylpyrazines, and labeling studies using [2-13C]glycine showed that those alkylpyrazines which increased in the presence of glycine had at least one 13C-labeled methyl substituent derived from glycine. The distribution of 13C within the pyrazines suggested two pathways by which glycine, and other amino acids, participate in alkylpyrazine formation, and showed the relative contribution of each pathway. Alkylpyrazines that involve glycine in both formation pathways displayed the largest relative increases with glycine addition. The study provided an insight into the sensitivity of alkylpyrazine formation to the amino acid composition in a heated food and demonstrated the importance of those amino acids that are able to contribute an alkyl substituent. This may aid in estimating the impact of amino acid addition on pyrazine formation, when amino acids are added to foods for acrylamide mitigation. Keywords: Pyrazines; glycine; acrylamide; potato; dihydropyrazines; α-dicarbonyls; Strecker aldehydes; 2,3-butanedione; formaldehyde |
| doi_str_mv | 10.1021/jf070044s |
| format | Article |
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The addition of glycine increased the quantities of several alkylpyrazines, and labeling studies using [2-13C]glycine showed that those alkylpyrazines which increased in the presence of glycine had at least one 13C-labeled methyl substituent derived from glycine. The distribution of 13C within the pyrazines suggested two pathways by which glycine, and other amino acids, participate in alkylpyrazine formation, and showed the relative contribution of each pathway. Alkylpyrazines that involve glycine in both formation pathways displayed the largest relative increases with glycine addition. The study provided an insight into the sensitivity of alkylpyrazine formation to the amino acid composition in a heated food and demonstrated the importance of those amino acids that are able to contribute an alkyl substituent. This may aid in estimating the impact of amino acid addition on pyrazine formation, when amino acids are added to foods for acrylamide mitigation. Keywords: Pyrazines; glycine; acrylamide; potato; dihydropyrazines; α-dicarbonyls; Strecker aldehydes; 2,3-butanedione; formaldehyde</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf070044s</identifier><identifier>PMID: 17447789</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Acrylamides - chemistry ; Alkylation ; alkylpyrazines ; amino acid composition ; amino acids ; Amino Acids - pharmacology ; baking ; Biological and medical sciences ; chemical reactions ; cooking ; flavor compounds ; food chemistry ; Food industries ; Food toxicology ; Fruit and vegetable industries ; Fundamental and applied biological sciences. Psychology ; glycine (amino acid) ; Glycine - administration & dosage ; Glycine - chemistry ; heat treatment ; Hot Temperature ; Isotopes ; model food systems ; potatoes ; pyrazines ; Pyrazines - chemistry ; Solanum tuberosum ; Solanum tuberosum - chemistry ; volatile compounds</subject><ispartof>Journal of agricultural and food chemistry, 2007-05, Vol.55 (10), p.4087-4094</ispartof><rights>Copyright © 2007 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a502t-2304668630928e189625a83542282ec3205f05ce70733f5783e08ac260e9f2113</citedby><cites>FETCH-LOGICAL-a502t-2304668630928e189625a83542282ec3205f05ce70733f5783e08ac260e9f2113</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/jf070044s$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf070044s$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27074,27922,27923,56736,56786</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18748199$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17447789$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Low, Mei Yin</creatorcontrib><creatorcontrib>Parker, Jane K.</creatorcontrib><creatorcontrib>Mottram, Donald S.</creatorcontrib><title>Mechanisms of Alkylpyrazine Formation in a Potato Model System Containing Added Glycine</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The use of glycine to limit acrylamide formation during the heating of a potato model system was also found to alter the relative proportions of alkylpyrazines. The addition of glycine increased the quantities of several alkylpyrazines, and labeling studies using [2-13C]glycine showed that those alkylpyrazines which increased in the presence of glycine had at least one 13C-labeled methyl substituent derived from glycine. The distribution of 13C within the pyrazines suggested two pathways by which glycine, and other amino acids, participate in alkylpyrazine formation, and showed the relative contribution of each pathway. Alkylpyrazines that involve glycine in both formation pathways displayed the largest relative increases with glycine addition. The study provided an insight into the sensitivity of alkylpyrazine formation to the amino acid composition in a heated food and demonstrated the importance of those amino acids that are able to contribute an alkyl substituent. This may aid in estimating the impact of amino acid addition on pyrazine formation, when amino acids are added to foods for acrylamide mitigation. Keywords: Pyrazines; glycine; acrylamide; potato; dihydropyrazines; α-dicarbonyls; Strecker aldehydes; 2,3-butanedione; formaldehyde</description><subject>Acrylamides - chemistry</subject><subject>Alkylation</subject><subject>alkylpyrazines</subject><subject>amino acid composition</subject><subject>amino acids</subject><subject>Amino Acids - pharmacology</subject><subject>baking</subject><subject>Biological and medical sciences</subject><subject>chemical reactions</subject><subject>cooking</subject><subject>flavor compounds</subject><subject>food chemistry</subject><subject>Food industries</subject><subject>Food toxicology</subject><subject>Fruit and vegetable industries</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>glycine (amino acid)</subject><subject>Glycine - administration & dosage</subject><subject>Glycine - chemistry</subject><subject>heat treatment</subject><subject>Hot Temperature</subject><subject>Isotopes</subject><subject>model food systems</subject><subject>potatoes</subject><subject>pyrazines</subject><subject>Pyrazines - chemistry</subject><subject>Solanum tuberosum</subject><subject>Solanum tuberosum - chemistry</subject><subject>volatile compounds</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0c1uEzEUBWALgWhaWPAC4A1ILAau_8aeZRSRgpSKSkkFO8t4PMXpjJ3aE4np0-MqUbNBYuXF_Xwsn4vQGwKfCFDyeduBBOA8P0MzIihUghD1HM2gDCslanKGznPeAoASEl6iMyI5l1I1M_TjytnfJvg8ZBw7PO_vpn43JfPgg8PLmAYz-hiwD9jg6ziaMeKr2Loer6c8ugEvYhiNDz7c4nnbuhZf9pMtd1-hF53ps3t9PC_QzfLLZvG1Wn2__LaYryojgI4VZcDrWtUMGqocUU1NhVFMcEoVdZZREB0I6yRIxjohFXOgjKU1uKajhLAL9OGQu0vxfu_yqAefret7E1zcZy2BS8Ia9V9IgStOeVPgxwO0KeacXKd3yQ8mTZqAfqxbP9Vd7Ntj6P7X4NqTPPZbwPsjMNmavksmWJ9PTkmuSPPoqoPzpdU_T3OT7nQtmRR6c73Wy2aj6Iot9M_i3x18Z6I2t6lk3qwpEAYgZSmPnl42Nutt3KdQ1vCPL_wFjtCo0Q</recordid><startdate>20070516</startdate><enddate>20070516</enddate><creator>Low, Mei Yin</creator><creator>Parker, Jane K.</creator><creator>Mottram, Donald S.</creator><general>American Chemical Society</general><scope>FBQ</scope><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>7QR</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20070516</creationdate><title>Mechanisms of Alkylpyrazine Formation in a Potato Model System Containing Added Glycine</title><author>Low, Mei Yin ; Parker, Jane K. ; Mottram, Donald S.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a502t-2304668630928e189625a83542282ec3205f05ce70733f5783e08ac260e9f2113</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Acrylamides - chemistry</topic><topic>Alkylation</topic><topic>alkylpyrazines</topic><topic>amino acid composition</topic><topic>amino acids</topic><topic>Amino Acids - pharmacology</topic><topic>baking</topic><topic>Biological and medical sciences</topic><topic>chemical reactions</topic><topic>cooking</topic><topic>flavor compounds</topic><topic>food chemistry</topic><topic>Food industries</topic><topic>Food toxicology</topic><topic>Fruit and vegetable industries</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>glycine (amino acid)</topic><topic>Glycine - administration & dosage</topic><topic>Glycine - chemistry</topic><topic>heat treatment</topic><topic>Hot Temperature</topic><topic>Isotopes</topic><topic>model food systems</topic><topic>potatoes</topic><topic>pyrazines</topic><topic>Pyrazines - chemistry</topic><topic>Solanum tuberosum</topic><topic>Solanum tuberosum - chemistry</topic><topic>volatile compounds</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Low, Mei Yin</creatorcontrib><creatorcontrib>Parker, Jane K.</creatorcontrib><creatorcontrib>Mottram, Donald S.</creatorcontrib><collection>AGRIS</collection><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>Chemoreception Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</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>Low, Mei Yin</au><au>Parker, Jane K.</au><au>Mottram, Donald S.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Mechanisms of Alkylpyrazine Formation in a Potato Model System Containing Added Glycine</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2007-05-16</date><risdate>2007</risdate><volume>55</volume><issue>10</issue><spage>4087</spage><epage>4094</epage><pages>4087-4094</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>The use of glycine to limit acrylamide formation during the heating of a potato model system was also found to alter the relative proportions of alkylpyrazines. The addition of glycine increased the quantities of several alkylpyrazines, and labeling studies using [2-13C]glycine showed that those alkylpyrazines which increased in the presence of glycine had at least one 13C-labeled methyl substituent derived from glycine. The distribution of 13C within the pyrazines suggested two pathways by which glycine, and other amino acids, participate in alkylpyrazine formation, and showed the relative contribution of each pathway. Alkylpyrazines that involve glycine in both formation pathways displayed the largest relative increases with glycine addition. The study provided an insight into the sensitivity of alkylpyrazine formation to the amino acid composition in a heated food and demonstrated the importance of those amino acids that are able to contribute an alkyl substituent. This may aid in estimating the impact of amino acid addition on pyrazine formation, when amino acids are added to foods for acrylamide mitigation. Keywords: Pyrazines; glycine; acrylamide; potato; dihydropyrazines; α-dicarbonyls; Strecker aldehydes; 2,3-butanedione; formaldehyde</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17447789</pmid><doi>10.1021/jf070044s</doi><tpages>8</tpages></addata></record> |
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| subjects | Acrylamides - chemistry Alkylation alkylpyrazines amino acid composition amino acids Amino Acids - pharmacology baking Biological and medical sciences chemical reactions cooking flavor compounds food chemistry Food industries Food toxicology Fruit and vegetable industries Fundamental and applied biological sciences. Psychology glycine (amino acid) Glycine - administration & dosage Glycine - chemistry heat treatment Hot Temperature Isotopes model food systems potatoes pyrazines Pyrazines - chemistry Solanum tuberosum Solanum tuberosum - chemistry volatile compounds |
| title | Mechanisms of Alkylpyrazine Formation in a Potato Model System Containing Added Glycine |
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