Abstract
Small peptides are involved in countless biological processes. Hence selective binding motifs for peptides can be powerful tools for labeling or inhibition. Finding those binding motifs, especially in water which competes for intermolecular H-bonds, poses an enormous challenge. A dynamic combinatorial library can be a powerful method to overcome this issue. We previously reported artificial receptors emerging form a dynamic combinatorial library of peptide building blocks. In this study we aimed to broaden this scope towards recognition of small peptides. Employing CXC peptide building blocks, we found that cyclic dimers of oxidized CFC bind to the aromatic peptides FF and YY (K ≈ 229–702 M−1), while AA binds significantly weaker (K ≈ 65–71 M−1).
Highlights
Peptides are one of the most abundant and structurally versatile motifs in nature
We previously reported artificial receptors emerging form a dynamic combinatorial library of peptide building blocks
Employing CXC peptide building blocks, we found that cyclic dimers of oxidized CFC bind to the aromatic peptides FF and YY (K ≈ 229–702 M−1), while AA binds significantly weaker (K ≈ 65–71 M−1)
Summary
Peptides are one of the most abundant and structurally versatile motifs in nature. selective binders for peptides are extremely desirable and highly challenging to design. Developments in artificial peptide recognition go back to the 1970’s when it was discovered that crown ethers can bind to ammonium functions, such as protonated amines in peptides [1]. Further such binding motifs were developed and if arranged correctly can be used to synthesize artificial receptors with high affinity [2,3]. Schmuck et al have been hugely successful in designing artificial peptide receptors [4,5] They combined a carboxylate binding site with an aromatic bowlshaped cavity, just the right size for a methyl group [6]. The equilibrium responds to stimuli such as addition of a template, which would stabilize a suitable receptor and amplifies its formation
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