Peptoids - oligomers of N-substituted glycine - are an important class of peptide mimics that are widely used in areas ranging from biology and medicine to metal binding and catalysis. The utility of peptoids, however, especially for applications in aqueous solutions, is often hampered by the hydrophobic nature of their sequences dictated by structural and functional requirements. Herein we describe a simple method to solubilize hydrophobic peptoids in water without modifying their original sequences, via the insertion of biocompatible and low cost piperazine or homopiperazine groups at the N- or C-terminus of the peptoid backbone. We show that our method can be applied for the production of α-, β- and azapeptoids, which display high water solubility for long periods of time. Moreover, circular dichroism (CD) spectroscopy revealed that the incorporation of piperazine groups within α-peptoids, having chiral naphthyl monomers, β-peptoids and unstructured azapeptoids results in peptoids that exhibit high conformational order in water.
Imidazo[1,5-a]pyridine is a significant structural component of a huge number of agrochemicals and pharmaceuticals. The synthesis of imidazo[1,5-a]pyridine has been a subject of intense research for numerous decades. A large...
Peptoids, N‐substituted glycine oligomers, represent an important class of peptidomimetics that can fold into three‐dimensional structures in solution. Most of the folded peptoid structures, however, resemble helices, and this can limit their applications, specifically in asymmetric catalysis. In this work, for the first time, unique examples of pyrrolidine‐based β‐turn‐like peptoids are described and characterized, both in the solid state, by single‐crystal X‐ray analysis, and in solution, by circular dichroism spectroscopy. Furthermore, their highly efficient and enantioselective catalytic activity for the production of γ‐nitro aldehydes by asymmetric Michael reaction in water was demonstrated. The structural properties and DFT‐D3 calculations of the new β‐turn‐like peptoids, as well as catalytic and spectroscopic studies on designed pyrrolidine‐based helical peptoids, suggest that the β‐turn structure plays a key role in the stereoselectivity of the catalytic reaction.
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