Synthesis, Absorption, and Fluorescence Studies of Coumaryl-Labelled Amino Acids and Dipeptides Linked Via Triazole Ring
Santosh Kumari A , Sunita Joshi B , S. M. Abdul Shakoor A , Devesh S. Agarwal A , Siva S. Panda C , Debi D. Pant B and Rajeev Sakhuja A D
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India.
B Department of Physics, Birla Institute of Technology and Science, Pilani 333 031, Rajasthan, India.
C Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA.
D Corresponding author. Email: sakhuja.rajeev@gmail.com
Australian Journal of Chemistry 68(9) 1415-1426 https://doi.org/10.1071/CH14708
Submitted: 11 December 2014 Accepted: 9 February 2015 Published: 7 April 2015
Abstract
Fluorophores based on 4-triazolyl, 7-hydroxy-4-triazolylmethyl, 4-O-triazolylmethyl, and 7-O-triazolylmethyl coumaryl-tagged amino acids and dipeptides were synthesized by copper-catalyzed [3 + 2] cycloaddition reaction between azido- or alkynyl-functionalized coumarins with alkynyl- or azido-functionalized amino acid and dipeptides in good-to-excellent yields. Steady-state absorption and the fluorescence properties of the synthesized conjugates were studied. The chemical applicability of these amino acid and peptide-based fluorophores was successfully demonstrated by their linear elongation by further tagging them with appropriate C- or N-terminus amino acid.
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