Carvalho, M. Fernanda N. N.Ferreira, M. JoaoKnittel, Ana S. O.Oliveira, Maria da C.Pessoa, Joao C.Herrmann, RudolfWagner, Gabriele2016-05-272016-05-272016-04-18Carvalho, 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.12.7310.3762/bjoc.12.73http://hdl.handle.net/10034/610874A 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.enhttp://creativecommons.org/licenses/by-nc-nd/4.0/Amino acidsCamphorsulfonylimineDFT calculationsNMR characterizationStrecker degradationArticle1860-5397Beilstein Journal of Organic Chemistry