Publication Type Journal Article
Title Strecker degradation of amino acids promoted by a camphor-derived sulfonamide
Authors M Fernanda NN Carvalho M J Ferreira Ana S. O. Knittel M. Conceição Oliveira J.C. Pessoa Rudolf Herrmann Gabriele Wagner
Groups BioMol BIOIN
Journal BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Year 2016
Month April
Volume 12
Number
Pages 732-744
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.
DOI http://dx.doi.org/10.3762/bjoc.12.73
ISBN
Publisher BEILSTEIN-INSTITUT
Book Title
ISSN 1860-5397
EISSN
Conference Name
Bibtex ID ISI:000374467900001
Observations
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