Clickable Coumarins as Fluorescent Labels for Amino Acids

Abstract

Seven trifunctional conjugates of Fmoc-protected amino acids with alkynyloxy-substituted coumarins have been prepared and spectroscopically characterized. The coumarin core was either coupled to the α or side chain amino group. This design allows for the linear or branched elongation to peptides or peptidomimetics. The synthetic potential of the conjugates was demonstrated by copper­-catalyzed [3+2] cycloadditions to orthogonally protected peptidomimetic products as well as a biotinylated fluorescent amino acid.

Key words

amino acids - coumarins - cycloaddition - fluorescent ­label - Mitsunobu reaction

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