Proline-Based Boronic Acid Receptors for Chiral Recognition of Glucose

Lin-E Guo, Yuan Hong, Shu-Ying Zhang, Miao Zhang, Xiao-Sheng Yan, Jin-Lian Cao, Zhao Li, Tony D James, Yun-Bao Jiang

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

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 in-troduction 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 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 der-ivation diversity available, our strategy to use proline-based receptors for chiral recognition holds significant promise for extension to other chiral systems.

Original languageEnglish
Number of pages8
JournalJournal of Organic Chemistry
Early online date22 Nov 2018
DOIs
Publication statusE-pub ahead of print - 22 Nov 2018

Cite this

Guo, L-E., Hong, Y., Zhang, S-Y., Zhang, M., Yan, X-S., Cao, J-L., ... Jiang, Y-B. (2018). Proline-Based Boronic Acid Receptors for Chiral Recognition of Glucose. Journal of Organic Chemistry. https://doi.org/10.1021/acs.joc.8b02425

Proline-Based Boronic Acid Receptors for Chiral Recognition of Glucose. / Guo, Lin-E; Hong, Yuan; Zhang, Shu-Ying; Zhang, Miao; Yan, Xiao-Sheng; Cao, Jin-Lian; Li, Zhao; James, Tony D; Jiang, Yun-Bao.

In: Journal of Organic Chemistry, 22.11.2018.

Research output: Contribution to journalArticle

Guo, Lin-E ; Hong, Yuan ; Zhang, Shu-Ying ; Zhang, Miao ; Yan, Xiao-Sheng ; Cao, Jin-Lian ; Li, Zhao ; James, Tony D ; Jiang, Yun-Bao. / Proline-Based Boronic Acid Receptors for Chiral Recognition of Glucose. In: Journal of Organic Chemistry. 2018.
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