ArticleAngewandte Chemie (International ed. in English)2022
Differential Peptide Multi-Macrocyclizations at the Surface of a Helical Foldamer Template.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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Who cites it
2 citing papers in PubMed.
- Interfacing B-DNA and DNA Mimic Foldamers.Angewandte Chemie (International ed. in English) · 2025Article
- Differential Peptide Multi-Macrocyclizations at the Surface of a Helical Foldamer Template.Angewandte Chemie (International ed. in English) · 2022Article
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3 authors.
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Abstract
Hybrid sequences comprising a peptide with several Cys residues and an aromatic foldamer helix with several chloroacetamide functions at its surface were synthesized. Such products may in principle form numerous macromulticyclic thioether products by intramolecularly combining all Cys residues and all chloroacetamide functions. However, we show that the reactive sites on the structurally defined helix can be placed at such locations that the peptide selectively stitches itself to form a series of different macrocycles within mostly one preferred product. Reactions were monitored by HPLC and products with two, three or four macrocycles were identified using LC-MS and NMR. The series of selective macrocyclizations define a sort of reaction trail where reaction sites otherwise identical are involved successively because of their precise positioning in space. The trails can be predicted to a large extent based on structural considerations and the assumption that smaller macrocycles form faster.
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