Generation of Dynamic Combinatorial Libraries Using Hydrazone-Functionalized Surface Mimetics

European Journal of Organic Chemistry
Sarah H Hewitt, Andrew J Wilson

Abstract

Dynamic combinatorial chemistry (DCC) represents an approach, whereby traditional supramolecular scaffolds used for protein surface recognition might be exploited to achieve selective high affinity target recognition. Synthesis, in situ screening and amplification under selection pressure allows the generation of ligands, which bear different moieties capable of making multivalent non-covalent interactions with target proteins. Generic tetracarboxyphenyl porphyrin scaffolds bearing four hydrazide moieties have been used to form dynamic combinatorial libraries (DCLs) using aniline-catalyzed reversible hydrazone exchange reactions, in 10 % DMSO, 5 mm NH4OAc, at pH 6.75. High resolution mass spectrometry (HRMS) was used to monitor library composition and establish conditions under which equilibria were established.

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Citations

Jun 8, 2021·Chemical Science·Attila TököliTamás A Martinek
Nov 13, 2019·Journal of the American Chemical Society·Meixia He, Jean-Marie Lehn

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Methods Mentioned

BETA
column
column chromatography

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