How Cysteine Reacts with Citral:  An Unexpected Reaction of β,β-Disubstituted Acroleins with Cysteine Leading to Hexahydro-1,4-thiazepines

The reaction of β,β-disubstituted acroleins [3-methyl-2-butenal (1), 3-methyl-2-hexenal (2), and citral (3)] with cysteine gave 1:2 adducts of a novel structural type, namely hexahydro-1,4-thiazepines. To the best of our knowledge, the spontaneous formation of a seven-membered heterocycle from the a...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2005-11, Vol.53 (23), p.9244-9248
Main Authors: Starkenmann, Christian, Brauchli, Robert, Maurer, Bruno
Format: Article
Language:English
Subjects:
Acrolein - chemistry
Aldehydes - chemistry
Biological and medical sciences
Cysteamine - chemistry
Food industries
Fundamental and applied biological sciences. Psychology
Magnetic Resonance Spectroscopy
Monoterpenes - chemistry
Thiazepines - chemistry
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Summary:The reaction of β,β-disubstituted acroleins [3-methyl-2-butenal (1), 3-methyl-2-hexenal (2), and citral (3)] with cysteine gave 1:2 adducts of a novel structural type, namely hexahydro-1,4-thiazepines. To the best of our knowledge, the spontaneous formation of a seven-membered heterocycle from the addition of cysteine to α,β-unsaturated aldehydes is unprecedented. The adduct 6 obtained from citral, under acidic conditions, reacted further to give the new bicyclic compound 8. Keywords: Cysteine conjugates; Michael addition; α,β-unsaturated aldehydes; hexahydro-1,4-thiazepine; 1,4-thiazepane; 3-methyl-2-butenal; 3-methyl-2-hexenal; citral
ISSN:0021-8561
1520-5118
DOI:10.1021/jf051712h