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Molecules 2007, 12(5), 1170-1182; doi:10.3390/12051170
Article

Stereoselective Syntheses of Fluorescent Non-Natural Aromatic Amino Acids Based on Asymmetric Michael Additions

* ,  and
Department of Chemistry, School of Sciences, Shantou University, Shantou, Guangdong 515063, P. R. China
* Author to whom correspondence should be addressed.
Received: 10 May 2007 / Revised: 24 May 2007 / Accepted: 25 May 2007 / Published: 26 May 2007
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Abstract

Four fluorescent non-natural aromatic amino acids have been synthesized based on a key stereoselective Michael addition reaction. S-1-Phenylethylamine was employed as both the source of amine and the stereoselectivity controller. The overall yields were moderate (30-50%). Fluorescent properties of some of the fluorophores were also investigated. It was found that compounds with a dimethylamino group bonded to the aromatic ring display intramolecular charge transfer fluorescence.
Keywords: Aladan; fluorescent non-natural amino acids; asymmetric Michael addition; stereoselective synthesis Aladan; fluorescent non-natural amino acids; asymmetric Michael addition; stereoselective synthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Chen, H.; Zhong, X.; Wei, J. Stereoselective Syntheses of Fluorescent Non-Natural Aromatic Amino Acids Based on Asymmetric Michael Additions. Molecules 2007, 12, 1170-1182.

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