Chiroptical Sensing of Amino Acid Derivatives by Host–Guest Complexation with Cyclo[6]aramide
| Autor: | Jialiang Tang, Jiecheng Ji, Zejiang Liu, Yimin Cai, Yunzhi Shi, Cheng Yang, Xuebin Wang, Lihua Yuan |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Supramolecular chirality
Circular dichroism Macrocyclic Compounds Supramolecular chemistry Pharmaceutical Science Organic chemistry 010402 general chemistry 01 natural sciences Analytical Chemistry host–guest chemistry.chemical_compound QD241-441 Amide Drug Discovery Molecule Amino Acids Physical and Theoretical Chemistry chemistry.chemical_classification 010405 organic chemistry Communication amino acid ester Cationic polymerization Esters chiral recognition Combinatorial chemistry 0104 chemical sciences Amino acid circular dichroism chemistry Chemistry (miscellaneous) Molecular Medicine Density functional theory hydrogen-bonded macrocycle |
| Zdroj: | Molecules, Vol 26, Iss 4064, p 4064 (2021) Molecules |
| ISSN: | 1420-3049 |
| Popis: | A hydrogen-bonded (H-bonded) amide macrocycle was found to serve as an effective component in the host–guest assembly for a supramolecular chirality transfer process. Circular dichroism (CD) spectroscopy studies showed that the near-planar macrocycle could produce a CD response when combined with three of the twelve L-α-amino acid esters (all cryptochiral molecules) tested as possible guests. The host–guest complexation between the macrocycle and cationic guests was explored using NMR, revealing the presence of a strong affinity involving the multi-point recognition of guests. This was further corroborated by density functional theory (DFT) calculations. The present work proposes a new strategy for amplifying the CD signals of cryptochiral molecules by means of H-bonded macrocycle-based host–guest association, and is expected to be useful in designing supramolecular chiroptical sensing materials. |
| Databáze: | OpenAIRE |
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