ArticleChemical science2017
Optimizing side chains for crystal growth from water: a case study of aromatic amide foldamers.
Article in Chemical science, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Solvent Effects on the Conformational Preferences of 2,6-Pyridylcarboxamide Foldamers.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Analysis of heavy metal ions (Pb, Hg, Cr, Cd, As) capture & detection based on quinoline probe binding data.Scientific reports · 2025Article
- Supramolecular Synthons in Protein-Ligand Frameworks.Crystal growth & design · 2024Article
- Controlling aromatic helix dimerization in water by tuning charge repulsions.Chemical science · 2023Article
- Directing the Self-Assembly of Aromatic Foldamer Helices using Acridine Appendages and Metal Coordination.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Generalizing the Aromatic δ-Amino Acid Foldamer Helix.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Discrete Stacked Dimers of Aromatic Oligoamide Helices.Angewandte Chemie (International ed. in English) · 2022Article
- Conformational interplay in hybrid peptide-helical aromatic foldamer macrocycles.Chemical science · 2021Article
- Loading Linear Arrays of CuAngewandte Chemie (International ed. in English) · 2021Article
- Internalization of Foldamer-Based DNA Mimics through a Site-Specific Antibody Conjugate to Target HER2-Positive Cancer Cells.Pharmaceuticals (Basel, Switzerland) · 2021Article
- Aromatic Foldamer Helices as α-Helix Extended Surface Mimetics.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Hybrid Sequences that Express both Aromatic Amide and α-Peptidic Folding Features.ChemPlusChem · 2020Article
- 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
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Authors and funding
6 authors.
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Abstract
The growth of crystals of aromatic compounds from water much depends on the nature of the water solubilizing functions that they carry. Rationalizing crystallization from water, and structure elucidation, of aromatic molecular and supramolecular systems is of general value across various fields of chemistry. Taking helical aromatic foldamers as a test case, we have validated several short polar side chains as efficient substituents to provide both solubility in, and crystal growth ability from, water. New 8-amino-2-quinolinecarboxylic acids bearing charged or neutral aminomethyl, carboxymethyl, sulfonic acid, or bis(hydroxymethyl)-methoxy side chains in position 4 or 5, were prepared on a multi gram scale. Fmoc protection of the main chain amine and suitable protections of the side chains ensured compatibility with solid phase synthesis. One tetrameric and five octameric oligoamides displaying these side chains were synthesized and shown to be soluble in water. In all cases but one, crystals were obtained using the hanging drop method, thus validating the initial design principle to combine polarity and rigidity. The only case that resisted crystallization appeared to be due to exceedingly high water solubility endowed by eight sulfonic acid functions. The neutral side chain did provide crystal growth ability from water but contributed poorly to solubility.
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