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
Affiliation
Universidade de Lisboa; University of Augsburg; University of ChesterPublication Date
2016-04-18
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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.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.12.73Publisher
Beilstein-InstitutAdditional Links
http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-12-73Type
ArticleLanguage
enEISSN
1860-5397ae974a485f413a2113503eed53cd6c53
10.3762/bjoc.12.73
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