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Strecker degradation of amino acids promoted by a camphor-derived sulfonamide

dc.contributor.authorCarvalho, M. Fernanda N. N.*
dc.contributor.authorFerreira, M. Joao*
dc.contributor.authorKnittel, Ana S. O.*
dc.contributor.authorOliveira, Maria da C.*
dc.contributor.authorPessoa, Joao C.*
dc.contributor.authorHerrmann, Rudolf*
dc.contributor.authorWagner, Gabriele*
dc.date.accessioned2016-05-27T09:39:53Z
dc.date.available2016-05-27T09:39:53Z
dc.date.issued2016-04-18
dc.identifier.citationCarvalho, M. F. N. N., Ferreira, M. J., Knittel, A. S. O., Oliveira, M. C., Pessoa, J. C., Herrmann, R., & Wagner, G. (2016). Strecker degradation of amino acids promoted by a camphor-derived sulfonamide. Beilstein Journal of Organic Chemistry, 12, 732-744. DOI: 10.3762/bjoc.12.73en
dc.identifier.doi10.3762/bjoc.12.73
dc.identifier.urihttp://hdl.handle.net/10034/610874
dc.description.abstractA camphor-derived sulfonimine with a conjugated carbonyl group, oxoimine 1 (O2SNC10H13O), reacts with amino acids (glycine, L-alanine, L-phenylalanine, L-leucine) to form a compound O2SNC10H13NC10H14NSO2 (2) which was characterized by spectroscopic means (MS and NMR) and supported by DFT calculations. The product, a single diastereoisomer, contains two oxoimine units connected by a –N= bridge, and thus has a structural analogy to the colored product Ruhemann´s purple obtained by the ninhydrin reaction with amino acids. A plausible reaction mechanism that involves zwitterions, a Strecker degradation of an intermediate imine and water-catalyzed tautomerizations was developed by means of DFT calculations on potential transition states.
dc.language.isoenen
dc.publisherBeilstein-Instituten
dc.relation.urlhttp://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-12-73en
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/en
dc.subjectAmino acidsen
dc.subjectCamphorsulfonylimineen
dc.subjectDFT calculationsen
dc.subjectNMR characterizationen
dc.subjectStrecker degradationen
dc.titleStrecker degradation of amino acids promoted by a camphor-derived sulfonamideen
dc.typeArticleen
dc.identifier.eissn1860-5397
dc.contributor.departmentUniversidade de Lisboa; University of Augsburg; University of Chesteren
dc.identifier.journalBeilstein Journal of Organic Chemistry
or.grant.openaccessYesen
rioxxterms.funderFCT-Fundação para a Ciência e Tecnologiaen
rioxxterms.identifier.projectFCT-Fundação para a Ciência e Tecnologiaen
rioxxterms.versionAMen
rioxxterms.versionofrecordhttps://doi.org/10.3762/bjoc.12.73
rioxxterms.licenseref.startdate2016-04-18
html.description.abstractA camphor-derived sulfonimine with a conjugated carbonyl group, oxoimine 1 (O2SNC10H13O), reacts with amino acids (glycine, L-alanine, L-phenylalanine, L-leucine) to form a compound O2SNC10H13NC10H14NSO2 (2) which was characterized by spectroscopic means (MS and NMR) and supported by DFT calculations. The product, a single diastereoisomer, contains two oxoimine units connected by a –N= bridge, and thus has a structural analogy to the colored product Ruhemann´s purple obtained by the ninhydrin reaction with amino acids. A plausible reaction mechanism that involves zwitterions, a Strecker degradation of an intermediate imine and water-catalyzed tautomerizations was developed by means of DFT calculations on potential transition states.
rioxxterms.publicationdate2016-04-18
dc.dateAccepted2016-03-24
dc.date.deposited2016-05-27


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