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Strecker degradation of amino acids promoted by a camphor-derived sulfonamide
Carvalho, M. Fernanda N. N. Ferreira, M. Joao Knittel, Ana S. O. Oliveira, Maria da C. Pessoa, Joao C. Herrmann, Rudolf Wagner, Gabriele
Carvalho, M. Fernanda N. N.
Ferreira, M. Joao
Knittel, Ana S. O.
Oliveira, Maria da C.
Pessoa, Joao C.
Herrmann, Rudolf
Wagner, Gabriele
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EPub Date
Publication Date
2016-04-18
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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.
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
Research Unit
DOI
10.3762/bjoc.12.73
PubMed ID
PubMed Central ID
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Article
Language
en
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ISSN
EISSN
1860-5397