Role of Intramolecular Aromatic π-π Interactions in the Self-Assembly of Di-l -Phenylalanine Dipeptide Driven by Intermolecular Interactions: Effect of Alanine Substitution
| Autor: | Samala Murali Mohan Reddy, Ganesh Shanmugam |
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| Rok vydání: | 2016 |
| Předmět: |
Surface Properties
Stereochemistry 02 engineering and technology 010402 general chemistry 01 natural sciences chemistry.chemical_compound Molecule Non-covalent interactions Pi interaction Particle Size Physical and Theoretical Chemistry Diphenylalanine Alanine chemistry.chemical_classification Dipeptide Molecular Structure Phenylpropionates Intermolecular force Dipeptides 021001 nanoscience & nanotechnology Atomic and Molecular Physics and Optics 0104 chemical sciences chemistry Intramolecular force 0210 nano-technology |
| Zdroj: | ChemPhysChem. 17:2897-2907 |
| ISSN: | 1439-4235 |
| DOI: | 10.1002/cphc.201600364 |
| Popis: | Although the role of intermolecular aromatic π-π interactions in the self-assembly of di-l-phenylalanine (l-Phe-l-Phe, FF), a peptide that is known for hierarchical structure, is well established, the influence of intramolecular π-π interactions on the morphology of the self-assembled structure of FF has not been studied. Herein, the role of intramolecular aromatic π-π interactions is investigated for FF and analogous alanine (Ala)-containing dipeptides, namely, l-Phe-l-Ala (FA) and l-Ala-l-Phe (AF). The results reveal that these dipeptides not only form self-assemblies, but also exhibit remarkable differences in structural morphology. The morphological differences between FF and the analogues indicate the importance of intramolecular π-π interactions, and the structural difference between FA and AF demonstrates the crucial role of the nature of intramolecular side-chain interactions (aromatic-aliphatic or aliphatic-aromatic), in addition to intermolecular interactions, in deciding the final morphology of the self-assembled structure. The current results emphasise that intramolecular aromatic π-π interaction may not be essential to induce self-assembly in smaller peptides, and π (aromatic)-alkyl or alkyl-π (aromatic) interactions may be sufficient. This work also illustrates the versatility of aromatic and a combination of aromatic and aliphatic residues in dipeptides in the formation of structurally diverse self-assembled structures. |
| Databáze: | OpenAIRE |
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