ArticleNature protocols2013
Large-scale and chromatography-free synthesis of an octameric quinoline-based aromatic amide helical foldamer.
Article in Nature protocols, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 52 citations in OpenAlex.
- Probing the Nonlinear Chiroptical Activity of Multiturn Aromatic Helices Using Linearly Polarized Light.Angewandte Chemie (International ed. in English) · 2025Article
- A glycan foldamer that uses carbohydrate-aromatic interactions to perform catalysis.Nature chemistry · 2025Article
- Design of an abiotic unimolecular three-helix bundle.Chemical science · 2025Article
- Single-Stranded Nucleic Acid Transmembrane Molecular Carriers Based on Positively Charged Helical Foldamers.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Directing the Self-Assembly of Aromatic Foldamer Helices using Acridine Appendages and Metal Coordination.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Loading Linear Arrays of CuAngewandte Chemie (International ed. in English) · 2021Article
- Sensing a binding event through charge transport variations using an aromatic oligoamide capsule.Chemical science · 2021Article
- Oligo-Quinolylene-Vinylene Foldamers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Carboxylate-functionalized foldamer inhibitors of HIV-1 integrase and Topoisomerase 1: artificial analogues of DNA mimic proteins.Nucleic acids research · 2019Article
- Single helically folded aromatic oligoamides that mimic the charge surface of double-stranded B-DNA.Nature chemistry · 2018Article
- Preparative scale and convenient synthesis of a water-soluble, deep cavitand.Nature protocols · 2016Article
- Iterative design of a helically folded aromatic oligoamide sequence for the selective encapsulation of fructose.Nature chemistry · 2015Article
Corrections and comments
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Authors and funding
3 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The synthesis of helical aromatic oligoamide foldamers derived from 8-amino-2-quinolinecarboxylic acid is described. The precursors are commercially available and products up to and including the octamer are obtained. The procedure covers the synthesis of the monomer, reduction of N-terminal nitro groups into amines, saponification of C-terminal methyl esters to form carboxylic acids, and coupling of amines and acids to form amides via acid chloride activation. Emphasis is given to how these reactions can be scaled up and how purification can be greatly simplified using recrystallization methods, thus providing considerable improvements over previously described procedures. As an illustration of the improvement, 8.4 g of an octamer can now reliably be prepared from a nitro-ester monomer in a matter of 8 (working) weeks without any chromatography.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.