Structure and reactions of the peroxy radicals of glycine and alanine in peptides: an ab initio study
Identifieur interne : 002C22 ( Main/Exploration ); précédent : 002C21; suivant : 002C23Structure and reactions of the peroxy radicals of glycine and alanine in peptides: an ab initio study
Auteurs : Mei Lan Huang [Canada, Royaume-Uni] ; Arvi Rauk [Canada]Source :
- Journal of Physical Organic Chemistry [ 0894-3230 ] ; 2004-09.
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Abstract
Ab initio calculations at the B3LYP/6‐31G(d) and CBS‐RAD level were carried out to investigate the reaction of αC‐centered peroxy radicals of neutral, non‐zwitterionic glycine and alanine (AH), and as residues in model peptides, N‐formylglycinamide and N‐formylalaninamide (PH). Bond dissociation enthalpies (BDEs) were calculated for the αC—O (D COα), O—O (DOO) and O—H (DOH) bonds of glycine and alanine peroxy radicals (AOO, POO) and hydroperoxides (AOOH, POOH). The predicted BDEs at 298 K, in kJ mol−1 are AOO(Gly), D COα = 70; AOO(Ala), D COα = 69; POO(Gly), D COα = 89; POO(Ala), D COα = 86; AOOH(Gly), D COα = 237, DOO = 203, DOH = 371; AOOH(Ala), D COα = 234, DOO = 195, DOH = 368; POOH(Gly), D COα = 266, DOO = 207, DOH = 380; POOH(Ala), D COα = 264, DOO = 208, DOH=383. Values of BDE of the peptides in β‐sheet peptide conformations were also estimated by constraining the Ramachandran dihedral angles, Φ and Ψ to, values of −150° and +150°: (S)‐POO(Gly), D COα = 99; (R)‐POO(Gly), D COα = 78; (S)‐POO(Ala), D COα = 88; (R)‐POO(Ala), D COα = 83; (S)‐POOH(Gly), D COα = 258, DOO = 195, DOH = 362; (R)‐POOH(Gly), D COα = 278, DOO = 217, DOH = 404; (S)‐ POOH(Ala), D COα = 240, DOO = 192, DOH = 355; (R)‐POOH(Ala), D COα = 270, DOO = 204, DOH = 390. The reactions of αC‐peroxy radicals, POO, and αC‐alkoxy radicals, PO, were studied in detail. Copyright © 2004 John Wiley & Sons, Ltd.
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DOI: 10.1002/poc.794
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<record><TEI wicri:istexFullTextTei="biblStruct"><teiHeader><fileDesc><titleStmt><title xml:lang="en">Structure and reactions of the peroxy radicals of glycine and alanine in peptides: an ab initio study</title><author><name sortKey="Huang, Mei Lan" sort="Huang, Mei Lan" uniqKey="Huang M" first="Mei Lan" last="Huang">Mei Lan Huang</name></author><author><name sortKey="Rauk, Arvi" sort="Rauk, Arvi" uniqKey="Rauk A" first="Arvi" last="Rauk">Arvi Rauk</name></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:7F7AD210C4008A1C828B138CD192DBE45981BBBA</idno><date when="2004" year="2004">2004</date><idno type="doi">10.1002/poc.794</idno><idno type="url">https://api-v5.istex.fr/document/7F7AD210C4008A1C828B138CD192DBE45981BBBA/fulltext/pdf</idno><idno type="wicri:Area/Istex/Corpus">002253</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">002253</idno><idno type="wicri:Area/Istex/Curation">002253</idno><idno type="wicri:Area/Istex/Checkpoint">000D39</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Checkpoint">000D39</idno><idno type="wicri:doubleKey">0894-3230:2004:Huang M:structure:and:reactions</idno><idno type="wicri:Area/Main/Merge">002F83</idno><idno type="wicri:Area/Main/Curation">002C22</idno><idno type="wicri:Area/Main/Exploration">002C22</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main" xml:lang="en">Structure and reactions of the peroxy radicals of glycine and alanine in peptides: an ab initio study</title><author><name sortKey="Huang, Mei Lan" sort="Huang, Mei Lan" uniqKey="Huang M" first="Mei Lan" last="Huang">Mei Lan Huang</name><affiliation wicri:level="4"><country xml:lang="fr">Canada</country><wicri:regionArea>Department of Chemistry, University of Calgary, 2500 University Drive, Calgary, Alberta</wicri:regionArea><orgName type="university">Université de Calgary</orgName><placeName><settlement type="city">Calgary</settlement><region type="state">Alberta</region></placeName></affiliation><affiliation wicri:level="1"><country xml:lang="fr" wicri:curation="lc">Royaume-Uni</country><wicri:regionArea>Current Address: Department of Chemistry, Central Chemistry Laboratory, South Parks Road, Oxford OX1 3QH</wicri:regionArea><wicri:noRegion>Oxford OX1 3QH</wicri:noRegion></affiliation></author><author><name sortKey="Rauk, Arvi" sort="Rauk, Arvi" uniqKey="Rauk A" first="Arvi" last="Rauk">Arvi Rauk</name><affiliation wicri:level="4"><country xml:lang="fr">Canada</country><wicri:regionArea>Department of Chemistry, University of Calgary, 2500 University Drive, Calgary, Alberta</wicri:regionArea><orgName type="university">Université de Calgary</orgName><placeName><settlement type="city">Calgary</settlement><region type="state">Alberta</region></placeName></affiliation><affiliation wicri:level="4"><country xml:lang="fr" wicri:curation="lc">Canada</country><wicri:regionArea>Department of Chemistry, University of Calgary, 2500 University Drive, Calgary, Alberta</wicri:regionArea><orgName type="university">Université de Calgary</orgName><placeName><settlement type="city">Calgary</settlement><region type="state">Alberta</region></placeName></affiliation></author></analytic><monogr></monogr><series><title level="j">Journal of Physical Organic Chemistry</title><title level="j" type="abbrev">J. Phys. Org. Chem.</title><idno type="ISSN">0894-3230</idno><idno type="eISSN">1099-1395</idno><imprint><publisher>John Wiley & Sons, Ltd.</publisher><pubPlace>Chichester, UK</pubPlace><date type="published" when="2004-09">2004-09</date><biblScope unit="volume">17</biblScope><biblScope unit="issue">9</biblScope><biblScope unit="page" from="777">777</biblScope><biblScope unit="page" to="786">786</biblScope></imprint><idno type="ISSN">0894-3230</idno></series><idno type="istex">7F7AD210C4008A1C828B138CD192DBE45981BBBA</idno><idno type="DOI">10.1002/poc.794</idno><idno type="ArticleID">POC794</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0894-3230</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>ab initio</term><term>bond dissociation energies</term><term>isodesmic reaction</term><term>oxidation</term><term>peptide</term><term>peroxy radical</term><term>peroxyl radical</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Ab initio calculations at the B3LYP/6‐31G(d) and CBS‐RAD level were carried out to investigate the reaction of αC‐centered peroxy radicals of neutral, non‐zwitterionic glycine and alanine (AH), and as residues in model peptides, N‐formylglycinamide and N‐formylalaninamide (PH). Bond dissociation enthalpies (BDEs) were calculated for the αC—O (D COα), O—O (DOO) and O—H (DOH) bonds of glycine and alanine peroxy radicals (AOO, POO) and hydroperoxides (AOOH, POOH). The predicted BDEs at 298 K, in kJ mol−1 are AOO(Gly), D COα = 70; AOO(Ala), D COα = 69; POO(Gly), D COα = 89; POO(Ala), D COα = 86; AOOH(Gly), D COα = 237, DOO = 203, DOH = 371; AOOH(Ala), D COα = 234, DOO = 195, DOH = 368; POOH(Gly), D COα = 266, DOO = 207, DOH = 380; POOH(Ala), D COα = 264, DOO = 208, DOH=383. Values of BDE of the peptides in β‐sheet peptide conformations were also estimated by constraining the Ramachandran dihedral angles, Φ and Ψ to, values of −150° and +150°: (S)‐POO(Gly), D COα = 99; (R)‐POO(Gly), D COα = 78; (S)‐POO(Ala), D COα = 88; (R)‐POO(Ala), D COα = 83; (S)‐POOH(Gly), D COα = 258, DOO = 195, DOH = 362; (R)‐POOH(Gly), D COα = 278, DOO = 217, DOH = 404; (S)‐ POOH(Ala), D COα = 240, DOO = 192, DOH = 355; (R)‐POOH(Ala), D COα = 270, DOO = 204, DOH = 390. The reactions of αC‐peroxy radicals, POO, and αC‐alkoxy radicals, PO, were studied in detail. Copyright © 2004 John Wiley & Sons, Ltd.</div></front></TEI><affiliations><list><country><li>Canada</li><li>Royaume-Uni</li></country><region><li>Alberta</li></region><settlement><li>Calgary</li></settlement><orgName><li>Université de Calgary</li></orgName></list><tree><country name="Canada"><region name="Alberta"><name sortKey="Huang, Mei Lan" sort="Huang, Mei Lan" uniqKey="Huang M" first="Mei Lan" last="Huang">Mei Lan Huang</name></region><name sortKey="Rauk, Arvi" sort="Rauk, Arvi" uniqKey="Rauk A" first="Arvi" last="Rauk">Arvi Rauk</name><name sortKey="Rauk, Arvi" sort="Rauk, Arvi" uniqKey="Rauk A" first="Arvi" last="Rauk">Arvi Rauk</name></country><country name="Royaume-Uni"><noRegion><name sortKey="Huang, Mei Lan" sort="Huang, Mei Lan" uniqKey="Huang M" first="Mei Lan" last="Huang">Mei Lan Huang</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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