Strecker degradation of amino acids promoted by a camphor-derived sulfonamide
AuthorsCarvalho, M. Fernanda N. N.
Ferreira, M. Joao
Knittel, Ana S. O.
Oliveira, Maria da C.
Pessoa, Joao C.
AffiliationUniversidade de Lisboa; University of Augsburg; University of Chester
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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.
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.12.73
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