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Synthesis 2008(13): 2013-2022  
DOI: 10.1055/s-2008-1067078
PAPER
© Georg Thieme Verlag Stuttgart · New York

Chiral N-(Coumarin-3-ylcarbonyl)-α-amino Acids: Fluorescent Markers for Amino Acids and Dipeptides

Alan R. Katritzky*, Tamari Narindoshvili, Parul Angrish
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA
Fax: +1(352)3929199; e-Mail: katritzky@chem.ufl.edu;
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Publication History

Received 17 January 2008
Publication Date:
16 May 2008 (online)

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Abstract

N-(Coumarin-3-ylcarbonyl)benzotriazole has been coupled with free amino acids, N-terminal-protected lysines and dipeptides to afford fluorescent amino acids and dipeptides (76-89% yield) with retention of original chirality. N α- and N ε-Coumarin-labeled­ lysines are obtained by simple, two-step procedures. N α-Cbz-N ε-(Coumarin-3-ylcarbonyl)-l-lysine is demonstrated to be an optically active fluorescent marker for labeling amino acids in solution-phase syntheses.

Key words

amino acids - peptides - coupling - coumarin fluorophore - benzotriazole methodology

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36

Two compound numbers given as a combination within square brackets represent a racemate or a diastereomeric mixture; all single compound numbers represent enantiomers.

37

No signal was seen in the proton NMR spectra for the acid proton (COOH) for most of the free carboxylic acids; this signal is reported only for compounds 21b, 27 and [29a + 29a′].