Proline-Based Boronic Acid Receptors for Chiral Recognition of Glucose
| Autor: | Jinlian Cao, Shu-Ying Zhang, Tony D. James, Xiao-Sheng Yan, Miao Zhang, Zhao Li, Lin-E Guo, Yuan Hong, Yun-Bao Jiang |
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| Rok vydání: | 2018 |
| Předmět: |
Models
Molecular inorganic chemicals Proline Stereochemistry Carboxylic acid Molecular Conformation 010402 general chemistry 01 natural sciences chemistry.chemical_compound polycyclic compounds heterocyclic compounds Phenylboronic acid Receptor Amide bonds chemistry.chemical_classification 010405 organic chemistry organic chemicals Organic Chemistry Stereoisomerism Boronic Acids 0104 chemical sciences Glucose chemistry Proton NMR Amine gas treating Boronic acid |
| Zdroj: | Guo, L-E, Hong, Y, Zhang, S-Y, Zhang, M, Yan, X-S, Cao, J-L, Li, Z, James, T D & Jiang, Y-B 2018, ' Proline-Based Boronic Acid Receptors for Chiral Recognition of Glucose ', Journal of Organic Chemistry, vol. 83, no. 24, pp. 15128-15135 . https://doi.org/10.1021/acs.joc.8b02425 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | Chiral recognition remains a major challenge in the area of molecular receptor design. With this research, we set out to explore the use of proline-based receptors for chiral recognition. Importantly, the proline structure allows for the introduction of at least two different binding groups due to the availability of both an amine and carboxylic acid group. Here we report a proof-of-concept exploration into the chiral recognition of d/l-glucose as a model chiral species, which prefers to bind to at least two boronic acid groups. We evaluated several proline-based receptors incorporating two phenylboronic acid groups, respectively, at the N- and C-termini of the amino acid residue, via amide bonds. We confirmed that the receptors exhibited chiral recognition using CD, 1H NMR, and 19F NMR spectroscopy. Given the derivation diversity available, our strategy to use proline-based receptors for chiral recognition holds significant promise for extension to other chiral systems. |
| Databáze: | OpenAIRE |
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