Combinatorial libraries of diamidopyridine-derived ‘tweezer’ receptors and sequence selective binding of peptides

Arienzo, Rosa; Kilburn, Jeremy D.

doi:10.1016/s0040-4020(01)01111-5

Cited by 26 publications

(7 citation statements)

References 33 publications

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“…The binding affinity of the resin‐bound receptor 23 for dye‐labeled N ‐Ac‐Lys‐ D ‐Ala‐ D ‐Ala ( 13 ) was measured by determining the ability of the resin‐bound receptor to absorb the peptide guest from solution, following a previously described methodology 3c. 12 Thus, a known mass of resin 23 was incubated with a solution of guest 13 in an aqueous buffer and the change in the concentration of the guest in free solution was monitored by UV spectroscopy 12.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Unsymmetrical Tweezer Receptor Libraries and Identification of Receptors for Lys‐D‐Ala‐D‐Ala in Aqueous Solution

Shepherd

Gale

Jensen

et al. 2006

Chemistry A European J

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Libraries of "unsymmetrical" tweezer receptors, featuring a guanidinium head group as a carboxylate binding site and two independently synthesized peptidic arms, have been prepared and screened to identify receptors for the N-Ac-Lys-D-Ala-D-Ala tripeptide sequence. The binding properties of one such receptor structure, with dye-labeled N-Ac-Lys-D-Ala-D-Ala, were investigated. These studies demonstrated that when attached to the solid-phase, the receptor binds dye-labeled N-Ac-Lys-D-Ala-D-Ala, in buffered aqueous media, with mM binding affinity.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Unsymmetrical Tweezer Receptor Libraries and Identification of Receptors for Lys‐D‐Ala‐D‐Ala in Aqueous Solution

Shepherd

Gale

Jensen

et al. 2006

Chemistry A European J

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“…A series of ferrocene-based receptors have a "ball bearing" that reorganizes upon binding, 12,13 and molecular clips and tweezers have been designed to use flexible arms for guest recognition. [14][15][16] We present here a novel approach of using the rotaxane architecture to obtain hosts that have flexible, converging functional groups. Rotaxanes contain a cyclic compound threaded onto a linear molecule (axle), which has blocking groups on its ends to keep the ring from dethreading.…”

Section: Introductionmentioning

confidence: 99%

Structure−Function Relationship of Amino Acid−[2]Rotaxanes

Smukste

Smithrud

2003

J. Org. Chem.

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Synthetic methodology was developed to construct amino acid-[2]rotaxanes that have phenylalanine and 3,5-di-tert-butylbenzene as blocking groups and dibenzo-24-crown-8, derivatized with either N-acetylargininyl or a carboxylic group, as the ring. A relative measure of the intramolecular interaction energies between the functional groups in DMSO/water mixtures is obtained by comparing their pK(a) values. Rotaxane structures were investigated through 2D NMR analysis and molecular dynamics simulations. Association constants for complexes of amino acids and rotaxanes in various protonation states were determined in a variety of solvent systems by (1)H NMR analysis. The unique intracomponent interactions that exist in the rotaxanes and their ability to act as artificial receptors are discussed.

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“…The solid‐phase bound receptor 21 was used to determine an on‐bead binding constant with the dye‐labelled tetrapeptide 18 by determining the ability of the resin‐bound receptor to absorb the peptide guest from solution, using previously described methodology 3c,4a,4h,24. Thus a known mass of resin 21 was incubated with a solution of guest 18 in an aqueous buffer and the change in the concentration of the guest in free solution was monitored by UV spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

Rapid Sequencing of Split‐and‐Mix Peptide Receptor Libraries – Identification of Binding Partners for Val‐Val‐Ile‐Ala in Aqueous Solution

et al. 2007

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Split‐and‐mix peptide libraries have been encoded by capping cleavable, laddered sequences with p‐bromobenzoic acid, allowing rapid analysis of the cleaved ladder fragments by mass spectrometry. The encoding methodology has been applied to the synthesis of libraries of peptide receptors and a library of tripeptides functionalised with a bicyclic guanidinium unit has been successfully screened to identify binding partners for Val‐Val‐Ile‐Ala, the C‐terminal tetrapeptide sequence of the amyloid‐β protein, Aβ(1–42). (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Combinatorial libraries of diamidopyridine-derived ‘tweezer’ receptors and sequence selective binding of peptides

Cited by 26 publications

References 33 publications

Synthesis of Unsymmetrical Tweezer Receptor Libraries and Identification of Receptors for Lys‐D‐Ala‐D‐Ala in Aqueous Solution

Synthesis of Unsymmetrical Tweezer Receptor Libraries and Identification of Receptors for Lys‐D‐Ala‐D‐Ala in Aqueous Solution

Structure−Function Relationship of Amino Acid−[2]Rotaxanes

Rapid Sequencing of Split‐and‐Mix Peptide Receptor Libraries – Identification of Binding Partners for Val‐Val‐Ile‐Ala in Aqueous Solution

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