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

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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 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.

Original languageEnglish
Pages (from-to)15128-15135
Number of pages8
JournalJournal of Organic Chemistry
Volume83
Issue number24
Early online date22 Nov 2018
DOIs
Publication statusPublished - 21 Dec 2018

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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, 83(24), 15128-15135. https://doi.org/10.1021/acs.joc.8b02425