Stereoselective Syntheses of Fluorescent Non-Natural Aromatic Amino Acids Based on Asymmetric Michael Additions 英文参考文献.docVIP

Molecules 2007, 12, 1170-1182 molecules ISSN 1420-3049 ? 2007 by MDPI /molecules Full Paper Stereoselective Syntheses of Fluorescent Non-Natural Aromatic Amino Acids Based on Asymmetric Michael Additions Heru Chen *, Xianbin Zhong and Jin Wei Department of Chemistry, School of Sciences, Shantou University, Shantou, Guangdong 515063, P. R. China * Author to whom correspondence should be addressed; e-mail: hrchen@; Tel. (+86) 754 2902772; Fax (+86) 754 2902767 Received: 10 May 2007; in revised form: 24 May 2007 / Accepted: 25 May 2007 / Published: 26 May 2007 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. Introduction Due to the development of the nonsense (stop codon) suppression technique, it has been possible to site-specifically incorporate any non-natural amino acid into almost any protein [1]. One of the significant features of this progress is that it offers a tool of almost limitless potential, promising chemical biologists systematic protein structure/function studies of great precision [2]. The development of fluorescent non-natural amino acids relates to this purpose. This new type of amino acid could play both the roles of structural moiety and intrinsic fluorescent probe when incorporated  Molecules 2007, 12 1171 into target bioactive molecules. Consequently, mu