Single-atom substitution enables supramolecular diversity from dipeptide building blocks.
basic_science · Level V
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- Record sourced from PubMed, PMID 35179536.
- Also identified by DOI 10.1039/d1sm01824h.
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Abstract
Dipeptides are popular building blocks for supramolecular gels that do not persist in the environment and may find various applications. In this work, we show that a simple substitution on the aromatic side-chain of phenylalanine with either fluorine or iodine enables supramolecular diversity upon self-assembly at neutral pH, leading to hydrogels or crystals. Each building block is characterized by <sup>1</sup>H- and <sup>13</sup>C-NMR spectroscopy, LC-MS, circular dichroism, and molecular models. The supramolecular behaviour is monitored with a variety of techniques, including circular dichroism, oscillatory rheology, transmission electron microscopy, attenuated total reflectance Fourier-transformed infrared spectroscopy, visible Raman spectroscopy, synchrotron-radiation single-crystal X-ray diffraction and UV Resonance Raman spectroscopy, allowing key differences to be pinpointed amongst the halogenated analogues.
Medical subject headings
- Dipeptides
- Hydrogels