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Synthesis and Biological Evaluation of a Library of AGE-Related Amino Acid Triazole Crosslinkers
Icik, Esra Jolly, Anthony Löffler, Paul Agelidis, Nektarios Bugdayci, Bakiye Altevogt, Luca Bilitewski, Ursula Baro, Angelika LASCHAT, SABINE
Icik, Esra
Jolly, Anthony
Löffler, Paul
Agelidis, Nektarios
Bugdayci, Bakiye
Altevogt, Luca
Bilitewski, Ursula
Baro, Angelika
LASCHAT, SABINE
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2020-08-10
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Abstract
Three N‐Boc‐protected amino acids, l‐serine, l‐aspartic, and l‐glutamic acid, were either converted into their methyl azidoalkanoates or various alkynes via Bestmann‐Ohira strategy or via reaction with propargylamine and propargyl bromide, respectively. The Cu‐catalyzed click reaction provided a library of amino acid based triazoles, which were further N‐methylated to triazolium iodides or deprotected and precipitated as free amino acid triazole dihydrochlorides. The biological properties of all derivatives were investigated by cytotoxicity assay (against L929 mouse fibroblasts) and broth microdilution method (E. coli ΔTolC and S. aureus). First results reveal complete inactivity for triazolium iodides with cell viabilities and microbial growths nearly 100 %, indicating them as possible analogs of advanced glycation endproducts (AGEs).
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Eur J Org Chem 2020;2020(33):5368-5379 doi:10.1002/ejoc.202000811.
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en
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1434-193X
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Attribution-NonCommercial-ShareAlike 4.0 International