Fluorescence Labeling of Amino Acids and Peptides with 7-Aminocoumarins

Lisa Wirtz; Dagmar Auerbach; Gregor Jung; Uli Kazmaier

doi:10.1055/s-0031-1291145

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(13): 2005-2012
DOI: 10.1055/s-0031-1291145

paper

Fluorescence Labeling of Amino Acids and Peptides with 7-Aminocoumarins

Lisa Wirtz

^aInstitut für Organische Chemie, Universität des Saarlandes, 66123 Saarbrücken, Germany, Fax: +49(681)3022409 eMail: u.kazmaier@mx.uni-saarland.de

,

Dagmar Auerbach

^bBiophysikalische Chemie, Universität des Saarlandes, 66123 Saarbrücken, Germany

,

Gregor Jung

^bBiophysikalische Chemie, Universität des Saarlandes, 66123 Saarbrücken, Germany

,

Uli Kazmaier*

^aInstitut für Organische Chemie, Universität des Saarlandes, 66123 Saarbrücken, Germany, Fax: +49(681)3022409 eMail: u.kazmaier@mx.uni-saarland.de

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Abstract

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Abstract

Pechmann condensation is a straightforward protocol for the synthesis of alkynyl- and azido-substituted 7-(dialkylamino)coumarins, which can be coupled to amino acid and peptide derivatives by copper-catalyzed [3+2]-cycloaddition (click reaction) in high yield. This allows the introduction of these efficient fluorescence labels into biologically relevant molecules.

Key words

amino acids - click chemistry - cycloaddition - coumarins - fluorescence labeling - peptides

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