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Foldamer-Based Molecular Recognition
Abstract
The ordered solution conformation of a synthetic chain molecule has been used to create a high-affinity binding site for small-molecule guests. The diastereoselective complexation of chiral monoterpenes with an achiral, amphiphilic m -phenylene ethynylene oligomer is demonstrated by induced circular dichroism in polar solvents. The stoichiometry of this solvophobically driven, reversible complex is strictly 1:1. The results are interpreted as a preferential binding of the chiral guest to one of the oligomer's enantiomeric helical conformations. Evidence for binding within the hydrophobic tubular cavity of the helix is provided by studies on modified oligomers.
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Citations
Cited by
Yashima, E., Ousaka, N., Taura, D., Shimomura, K., Ikai, T., & Maeda, K. (2016) · Chemical Reviews · doi:10.1021/acs.chemrev.6b00354 · Cited by 2,004
Synthetic Helical Polymers: Conformation and Function
Nakano, T., & Okamoto, Y. (2001) · Chemical Reviews · doi:10.1021/cr0000978 · Cited by 1,375
Detection and Amplification of Chirality by Helical Polymers
Yashima, E., Maeda, K., & Nishimura, T. (2004) · Chemistry – A European Journal · doi:10.1002/chem.200305295 · Cited by 543
Chirality-Responsive Helical Polymers
Yashima, E., & Maeda, K. (2008) · Macromolecules · doi:10.1021/ma071453s · Cited by 441
Metadata
- Authors
- Prince, R. B., Barnes, S. A., & Moore, J. S.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2000-03-01
- Volume
- 122
- Issue
- 12
- Pages
- 2758-2762
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2033978239
- Cited by
- 354
- References
- 0
- FWCI
- 13.07
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: Foldamer-Based Molecular Recognition. https://app.cochat.ai/papers/10.1021/ja993830p
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- Prince, R. B., Barnes, S. A., & Moore, J. S. (2000). Foldamer-Based Molecular Recognition. Journal of the American Chemical Society. https://doi.org/10.1021/ja993830p
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
