Cooperative Multipoint Recognition of Sialic Acid by Benzoboroxole-Based Receptors Bearing Cationic Hydrogen-Bond Donors

Alice Di Pasquale, Stefano Tommasone, Lili Xu, Jing Ma, Paula M Mendes

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)
133 Downloads (Pure)

Abstract

Sialic acid recognition remains an interesting and challenging target in molecular receptor design. Herein, we report a series of benzoboroxole-based receptors in which cationic hydrogen-bond donors have been introduced and shown to promote multipoint sialic acid recognition. One striking feature revealed by these receptors is that the carboxylate sialic acid residue is the primary binding determinant for recognition by benzoboroxole, in which the presence of charge-reinforced hydrogen bonds results in enhanced selectivity for sialic acid over other carbohydrates and a 4.5-fold increase in affinity. These findings open up wide possibilities for benzoboroxole-based receptors use in life science research, biotechnology, and diagnostics.

Original languageEnglish
Pages (from-to)8330-8338
Number of pages9
JournalThe Journal of Organic Chemistry
Volume85
Issue number13
Early online date8 Jun 2020
DOIs
Publication statusPublished - 2 Jul 2020

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