Synthetic Lectin Mimics Artificial Carbohydrate Receptors

Molecular Basis of Mannose Recognition by Pradimicins and their Application to Microbial Cell Surface Imaging

“…The predominant issue in terms of carbohydrate recognition by small molecules is the competition between carbohydrates and water molecules (Davis, 2009;Yang et al, 2011). More specifically, the polyol structure of carbohydrates is easily reproduced by clusters of water molecules, rendering them difficult to capture in aqueous solvents.…”

“…To address the above issues, several strategies have been pursued in the area of supramolecular chemistry (Davis, 2009;Miron and Petitjean, 2015;Yang et al, 2011). The use of boronic acids, which form reversible covalent bonds with 1,2-or 1,3-diols, represents one strategy to bind carbohydrates in water (Jin et al, 2010;Zhai et al, 2015).…”

“…One prominent exception is Davis's cage-shaped molecules, which selectively recognize carbohydrates exhibiting an all-equatorial array of polar functionalities in water (Ferrand et al, 2007(Ferrand et al, , 2009; Ke et al, 2012;Sookcharoenpinyo et al, 2012). However, despite advances in our understanding of factors contributing carbohydrate recognition (Asensio, et al, 2013;Francesconi et al, 2018;Roldó s et al, 2011;Tromans et al, 2019;Yang et al, 2011), there remains a general lack of synthetic small molecules that bind one specific carbohydrate under physiological conditions.…”

Mannose-binding analysis and biological application of pradimicins

“…9), 48) which reflected the structural motifs characteristic of the cell wall mannans from Candida albicans. 49) Oligomannoses (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14) were synthesized via a stepwise or blockwise glycosylation strategy using thiomannoside 50) and mannosyl halide donors. 51),52) To estimate the relative binding affinity of PRM-A for these oligomannoses, we examined their antagonistic effects on the antifungal activity of PRM-A against Candida rugosa.…”

“…51),52) To estimate the relative binding affinity of PRM-A for these oligomannoses, we examined their antagonistic effects on the antifungal activity of PRM-A against Candida rugosa. Comparison of their minimum antagonistic concentrations (MACs) required for suppressing PRM-A (32 µg/mL)-induced growth inhibition of C. rugosa cells revealed that branched oligomannoses (8)(9)(10)(11)(12)(13)(14) with multiple non-reducing ends suppressed the antifungal activity of PRM-A more potently than Man-OMe and the linear oligomannoses (2-7), and the antagonistic effect of the branched oligomannoses correlated with the number of Man residues at their non-reducing ends. In addition, oligomannose mimics (15)(16)(17), in which two mannose units were connected by polyethylene glycol spacers, were found to exhibit MACs similar to those of two-branched oligomannoses (8)(9)(10)(11).…”