ArticleAngewandte Chemie (International ed. in English)2020
Improved Stability and Tunable Functionalization of Parallel β-Sheets via Multicomponent N-Alkylation of the Turn Moiety.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Exploration of the Tertiary Amide Chemical Space of Dolastatin 15 Analogs Reveals New Insights into the Structure-Anticancer Activity Relationship.ChemMedChem · 2025Article
- Unlocking Enol-Ugi-Derived Conformationally Restricted Peptidomimetic Motifs.The Journal of organic chemistry · 2025Article
- Influence ofMolecules (Basel, Switzerland) · 2021Article
- On-resin multicomponent protocols for biopolymer assembly and derivatization.Nature protocols · 2021Review
- Improving the Stability of Maleimide-Thiol Conjugation for Drug Targeting.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Improved Stability and Tunable Functionalization of Parallel β-Sheets via Multicomponent N-Alkylation of the Turn Moiety.Angewandte Chemie (International ed. in English) · 2020Article
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Authors and funding
6 authors.
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Abstract
In contrast to the myriad of methods available to produce α-helices and antiparallel β-sheets in synthetic peptides, just a few are known for the construction of stable, non-cyclic parallel β-sheets. Herein, we report an efficient on-resin approach for the assembly of parallel β-sheet peptides in which the N-alkylated turn moiety enhances the stability and gives access to a variety of functionalizations without modifying the parallel strands. The key synthetic step of this strategy is the multicomponent construction of an N-alkylated turn using the Ugi reaction on varied isocyano-resins. This four-component process assembles the orthogonally protected turn fragment and incorporates handles serving for labeling/conjugation purposes or for reducing peptide aggregation. NMR and circular dichroism analyses confirm the better-structured and more stable parallel β-sheets in the N-alkylated peptides compared to the non-functionalized variants.
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