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

نویسندگان

  • M Fernanda N N Carvalho
  • M João Ferreira
  • Ana S O Knittel
  • Maria da Conceição Oliveira
  • João Costa Pessoa
  • Rudolf Herrmann
  • Gabriele Wagner
چکیده

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.

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عنوان ژورنال:

دوره 12  شماره 

صفحات  -

تاریخ انتشار 2016