Abstract
GlcNAc2 is the core disaccharide fragment present in N‐glycans exposed on the surface of enveloped viruses of high health concern, such as coronaviruses. Because N‐glycans are directly involved in the docking of viruses to host cells, recognition of GlcNAc2 by a biomimetic receptor may be a convenient alternative to the use of lectins to interfere with viral entry and infection. Herein, we describe a simple biomimetic receptor recognizing the methyl‐β‐glycoside of GlcNAc2 in water with an unprecedented affinity of 160 μM, exceeding that of more structurally complex receptors reported in the literature. The tweezers‐shaped acyclic structure exhibits marked selectivity among structurally related disaccharides, and complete discrimination between mono‐ and disaccharides. Molecular modelling calculations supported by NOE data provided a three‐dimensional description of the binding mode, shedding light on the origin of the affinities and selectivities exhibited by the receptor.
Highlights
GlcNAc2 is the core disaccharide fragment present in N-glycans exposed on the surface of enveloped viruses of high health concern, such as coronaviruses
GlcNAc-binding lectins, such as NICTABA from Nicotiana tabacum and Urtica dioica Agglutinin (UDA), which target GlcNAc2 at the stem of Nglycosilation sites, possess a broad-spectrum activity against several families of enveloped viruses,[7] effective molecular recognition of GlcNAc2 in water by a simple and accessible biomimetic receptor can potentially represent a convenient alternative to natural lectins, because of advantages in terms of availability, molecular weight, purity, stability and immunogenicity
Selective recognition of neutral glycans by biomimetic receptors in physiological medium represents a major challenge of current research,[4,8] because water is a strong competitor for recognition of polar molecules such as carbohydrates.[9]
Summary
GlcNAc2 is the core disaccharide fragment present in N-glycans exposed on the surface of enveloped viruses of high health concern, such as coronaviruses. [b] Calculated from the log b values using the “BC50 Calculator” program.[15] [c] Receptor 1 dimerization constant (log bdim = 2.65 Æ 0.07) was set invariant in the nonlinear regression analysis of NMR and ITC data.
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