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Triangular prism-shaped β-peptoid helices as unique biomimetic scaffolds.

ABSTRACT: β-Peptoids are peptidomimetics based on N-alkylated β-aminopropionic acid residues (or N-alkyl-β-alanines). This type of peptide mimic has previously been incorporated in biologically active ligands and has been hypothesized to be able to exhibit foldamer properties. Here we show, for the first time, that β-peptoids can be tuned to fold into stable helical structures. We provide high-resolution X-ray crystal structures of homomeric β-peptoid hexamers, which reveal right-handed helical conformations with exactly three residues per turn and a helical pitch of 9.6-9.8 Å between turns. The presence of folded conformations in solution is supported by circular dichroism spectroscopy showing length- and solvent dependency, and molecular dynamics simulations provide further support for a stabilized helical secondary structure in organic solvent. We thus outline a framework for future design of novel biomimetics that display functional groups with high accuracy in three dimensions, which has potential for development of new functional materials.

SUBMITTER: Laursen JS

PROVIDER: S-EPMC4432622 | biostudies-literature | 2015 May

REPOSITORIES: biostudies-literature

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Triangular prism-shaped β-peptoid helices as unique biomimetic scaffolds.

Laursen Jonas S JS Harris Pernille P Fristrup Peter P Olsen Christian A CA

Nature communications 20150506

β-Peptoids are peptidomimetics based on N-alkylated β-aminopropionic acid residues (or N-alkyl-β-alanines). This type of peptide mimic has previously been incorporated in biologically active ligands and has been hypothesized to be able to exhibit foldamer properties. Here we show, for the first time, that β-peptoids can be tuned to fold into stable helical structures. We provide high-resolution X-ray crystal structures of homomeric β-peptoid hexamers, which reveal right-handed helical conformati ...[more]

PMID: 25943784

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Project description:Much experimental work has been contributed to all-metal σ, π and δ-aromaticity among transition metals, semimetallics and other metals in the past two decades. Before our focused investigations on the properties of triangular and sandwich-shaped all-metal aromatics, A. I. Boldyrev presented general discussions on the concepts of all-metal σ-aromaticity and σ-antiaromaticity for metallo-clusters. Schleyer illustrated that Nucleus-Independent Chemical Shifts (NICS) were among the most authoritative criteria for aromaticity. Ugalde discussed the earlier developments of all-metal aromatic compounds with all possible shapes. Besides the theoretical predictions, many stable all-metal aromatic trinuclear clusters have been isolated as the metallic analogues of either the σ-aromatic molecule's [H3]+ ion or the π-aromatic molecule's [C3H3]+ ion. Different from Hoffman's opinion on all-metal aromaticity, triangular all-metal aromatics were found to hold great potential in applications in coordination chemistry, catalysis, and material science. Triangular all-metal aromatics, which were theoretically proved to conform to the Hückel (4n + 2) rule and possess the smallest aromatic ring, could also play roles as stable ligands during the formation of all-metal sandwiches. The triangular and sandwich-shaped all-metal aromatics have not yet been specifically summarized despite their diversity of existence, puissant developments and various interesting applications. These findings are different from the public opinion that all-metal aromatics would be limited to further applications due to their overstated difficulties in synthesis and uncertain stabilities. Our review will specifically focus on the summarization of theoretical predictions, feasible syntheses and isolations, and multiple applications of triangular and sandwich shaped all-metal aromatics. The appropriateness and necessities of this review will emphasize and disseminate their importance and applications forcefully and in a timely manner.

Dataset Information

Triangular prism-shaped β-peptoid helices as unique biomimetic scaffolds.

Publications

Triangular prism-shaped β-peptoid helices as unique biomimetic scaffolds.

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