Issue 13, 2005

Internally stabilized selenocysteine derivatives: syntheses, 77Se NMR and biomimetic studies

Abstract

Selenocystine ([Sec]2) and aryl-substituted selenocysteine (Sec) derivatives are synthesized, starting from commercially available amino acid L-serine. These compounds are characterized by a number of analytical techniques such as NMR (1H, 13C and 77Se) and TOF mass spectroscopy. This study reveals that the introduction of amino/imino substituents capable of interacting with selenium may stabilize the Sec derivatives. This study further suggests that the oxidation–elimination reactions in Sec derivatives could be used for the generation of biologically active selenols having internally stabilizing substituents.

Graphical abstract: Internally stabilized selenocysteine derivatives: syntheses, 77Se NMR and biomimetic studies

Supplementary files

Article information

Article type
Paper
Submitted
15 Apr 2005
Accepted
11 May 2005
First published
09 Jun 2005

Org. Biomol. Chem., 2005,3, 2476-2481

Internally stabilized selenocysteine derivatives: syntheses, 77Se NMR and biomimetic studies

P. P. Phadnis and G. Mugesh, Org. Biomol. Chem., 2005, 3, 2476 DOI: 10.1039/B505299H

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