Synthesis 2011(1): 83-90  
DOI: 10.1055/s-0030-1258345
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Novel Fluorescent Aminoxy Acids and Aminoxy Hybrid Peptides

Alan R. Katritzky*a, Abdelmotaal Abdelmajeida,b, Srinivasa R. Talaa, M. S. Amineb, Peter J. Steelca Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611, USA
Fax: +1(352)3920554; e-Mail: katritzky@chem.ufl.edu;
b Department of Chemistry, Faculty of Science, Benha University, Benha, Egypt
c Chemistry Department, University of Canterbury, Christchurch, New Zealand
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Publication History

Received 2 September 2010
Publication Date:
30 November 2010 (eFirst)

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Abstract

α-Aminoxy acid conjugates and hybrid α-aminoxy dipeptide conjugates showing blue to green fluorescence (with quantum yields 0.23-0.71) were synthesized (75-92% yield) from N-acylbenzotriazoles. 7-Methoxycoumarin derivatives were obtained (quantum yields φ 0.35-0.71) that could be suitable for peptide assays. The wavelengths of the absorption maxima (λAbs) and the fluorescence emission maxima (λEm) and the quantum yields (φ) of some coumarin-3-ylcarbonyl aminoxy acid conjugates were comparable to those of the analogous amino acid derivatives.

Key words

fluorescence - acylations - amino acids - aminoxy acids - peptides