Synthesis of guanidinium-derived receptor libraries and screening for selective peptide receptors in water

Chemistry : a European Journal
Kim B JensenJeremy D Kilburn

Abstract

A library of "tweezer" receptors, incorporating a guanidinium "head group" and two peptide derived side arms has been prepared on the solid-phase using an orthogonally protected guanidinium scaffold 12. The library was screened with various tripeptide derivatives in an aqueous solvent system. A tweezer receptor 25 for the side chain protected tripeptide 19 was identified from the screening experiments. Receptor 25 was resynthesised and solution binding studies were carried out, which revealed that 25 binds to tripeptide 19 with K(a)=8.2 x 10(4) +/- 2.5 x 10(4) (15 % DMSO/H(2)O, pH 8.75) and with appreciable selectivity over the tripeptide enantiomer 22 and the side chain deprotected tripeptide 20.

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Citations

Jun 9, 2004·Current Opinion in Chemical Biology·Natarajan Srinivasan, Jeremy D Kilburn
Jan 6, 2007·Organic & Biomolecular Chemistry·Andrew J WilsonAndrew D Hamilton
Jun 13, 2017·Chemical Communications : Chem Comm·N DelsucI Hamachi
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May 24, 2007·Organic & Biomolecular Chemistry·Richard J FitzmauriceJeremy D Kilburn
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Sep 29, 2009·Expert Opinion on Therapeutic Patents·Franciszek Saczewski, Łukasz Balewski
Jan 27, 2009·Chemical Society Reviews·Stefan Kubik
Jan 4, 2012·Chemistry : a European Journal·Kah Hoe KongYulin Lam
Jan 11, 2005·Journal of Combinatorial Chemistry·Vicente del AmoAnthony P Davis
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Mar 31, 2005·Journal of the American Chemical Society·Shohei TashiroMakoto Fujita
Nov 13, 2010·Bioorganic & Medicinal Chemistry·Elena RivaDaniele Passarella

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