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Issue 9, 2003
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Metal-ion induced amplification of three receptors from dynamic combinatorial libraries of peptide-hydrazones

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Abstract

Three building blocks of general structure (MeO)2CH–aromatic linker–Pro–amino acid–NHNH2 have been prepared and tested in acid-catalysed dynamic combinatorial libraries. Exposure of these libraries to LiI and NaI led to the amplification of three macrocyclic pseudopeptide receptors. The receptors were isolated and their interactions with LiI and NaI were analysed using NMR, IR and ITC. Binding of the metal ions to the receptors is invariably entropy-driven. Nevertheless, all receptors were found to be flexible with substantial conformational rearrangements accompanying guest binding. This type of receptor is extremely difficult to access through rational design and the fact that dynamic combinatorial chemistry allows facile access to these challenging molecules underlines the power of the dynamic approach.

Graphical abstract: Metal-ion induced amplification of three receptors from dynamic combinatorial libraries of peptide-hydrazones

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Publication details

The article was received on 24 Jan 2003, accepted on 18 Mar 2003 and first published on 09 Apr 2003


Article type: Paper
DOI: 10.1039/B300956D
Citation: Org. Biomol. Chem., 2003,1, 1625-1633
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    Metal-ion induced amplification of three receptors from dynamic combinatorial libraries of peptide-hydrazones

    S. L. Roberts, R. L. E. Furlan, S. Otto and J. K. M. Sanders, Org. Biomol. Chem., 2003, 1, 1625
    DOI: 10.1039/B300956D

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