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

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dc.contributor.author Sakhuja, Rajeev
dc.contributor.author Bajaj, Kiran
dc.date.accessioned 2021-11-11T11:00:16Z
dc.date.available 2021-11-11T11:00:16Z
dc.date.issued 2016-06-22
dc.identifier.uri https://www.sciencedirect.com/science/article/pii/S0040403916305299?via%3Dihub
dc.identifier.uri http://dspace.bits-pilani.ac.in:8080/xmlui/handle/123456789/3367
dc.description.abstract 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 Csingle bondO and Csingle bondN 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. en_US
dc.language.iso en en_US
dc.publisher Elsiever en_US
dc.subject Chemistry en_US
dc.subject Amino acids en_US
dc.subject Copper Water en_US
dc.subject Catalysis Labelling en_US
dc.title Copper-catalysed Csingle bondN/Csingle bondO coupling in water: a facile access to N-coumaryl amino acids and fluorescent tyrosine & lysine labels en_US
dc.type Article en_US


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