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

Hdl Handle:
http://hdl.handle.net/10034/610874
Title:
Strecker degradation of amino acids promoted by a camphor-derived sulfonamide
Authors:
Carvalho, M. Fernanda N. N.; Ferreira, M. Joao; Knittel, Ana S. O.; Oliveira, Maria da C.; Pessoa, Joao C.; Herrmann, Rudolf; Wagner, Gabriele
Abstract:
A 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.
Affiliation:
Universidade de Lisboa; University of Augsburg; University of Chester
Citation:
Carvalho, 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.12.73
Publisher:
Beilstein-Institut
Journal:
Beilstein Journal of Organic Chemistry
Publication Date:
18-Apr-2016
URI:
http://hdl.handle.net/10034/610874
DOI:
10.3762/bjoc.12.73
Additional Links:
http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-12-73
Type:
Article
Language:
en
EISSN:
1860-5397
Appears in Collections:
Natural Sciences

Full metadata record

DC FieldValue Language
dc.contributor.authorCarvalho, M. Fernanda N. N.en
dc.contributor.authorFerreira, M. Joaoen
dc.contributor.authorKnittel, Ana S. O.en
dc.contributor.authorOliveira, Maria da C.en
dc.contributor.authorPessoa, Joao C.en
dc.contributor.authorHerrmann, Rudolfen
dc.contributor.authorWagner, Gabrieleen
dc.date.accessioned2016-05-27T09:39:53Zen
dc.date.available2016-05-27T09:39:53Zen
dc.date.issued2016-04-18en
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.12.73en
dc.identifier.urihttp://hdl.handle.net/10034/610874en
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.en
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.eissn1860-5397en
dc.contributor.departmentUniversidade de Lisboa; University of Augsburg; University of Chesteren
dc.identifier.journalBeilstein Journal of Organic Chemistryen
dc.date.accepted2016-03-24en
or.grant.openaccessYesen
rioxxterms.funderFCT-Fundação para a Ciência e Tecnologiaen
rioxxterms.identifier.projectFCT-Fundação para a Ciência e Tecnologiaen
rioxxterms.versionAMen
rioxxterms.licenseref.startdate2016-04-18en
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