原创力文档stereoselective syntheses of fluorescent non-natural aromatic amino acids based on asymmetric michael additions立体选择合成基于不对称的荧光非天然的芳香氨基酸迈克尔补充.pdfVIP
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stereoselective syntheses of fluorescent non-natural aromatic amino acids based on asymmetric michael additions立体选择合成基于不对称的荧光非天然的芳香氨基酸迈克尔补充
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
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