Copper-catalysed CN/CO coupling in water: a facile access to N-coumaryl amino acids and fluorescent tyrosine & lysine labels

Add time:09/05/2019    Source:sciencedirect.com

A mild, efficient, ligand free and environmentally benign approach towards the construction of sp2 C-sp3 N bond has been developed via copper catalysed Ullmann type of coupling between 4-chlorocoumarin with N-terminus unprotected amino acids in microwave-aqua conditions, yielding a series of N-coumaryl amino acids in good to excellent yields. Excellent photo-physical properties exhibited by these N-coumaryl amino acids and their chemical applicability as C-terminus coupling partners for N-terminus peptides make them potential fluorescent probes in labelling studies. The methodology was extended towards the CO and CN coupling for the synthesis of fluorescent coumaryl labelled tyrosine and lysine labels respectively. Application of coumaryl labelled tyrosine was further explored towards the synthesis of fluorescent labelled opioid tetrapeptide, Endomorphin-2 derivative.

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