Synthetic receptors for molecular recognition of carbohydrates

Abstract

Section 1. Modification of the receptor binding side-arms. 15 Design and Synthesis…………………………………………………………... 15 Binding studies and structure elucidation…………………………………….. 18 Section 2. Modification of the receptor scaffold. 27 Design and Synthesis…………………………………………………………... 27 Binding studies and structure elucidation…………………………………….. 30 Section 3. Modifications of the pyrrolic binding groups. 37 Design and Synthesis…………………………………………………………... 37 Binding studies and structure elucidation…………………………………….. 39 Section 4. Modifications of the aminic binding groups. 49 Design and Synthesis…………………………………………………………... 49 Binding studies and structure elucidation…………………………………….. 54 Conclusions and general remarks…………………………………………. 67 Experimental Section. 69 General…………………………………………………………………………… 69 Conformational Analysis -NMR methods……………………………………. 70 Conformational Analysis -Molecular Modeling……………………………... 70 Materials…………………………………………………………………………..

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

“…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). Tripod-and cage-shaped molecules can act as lectin mimics, which accommodate carbohydrates through non-covalent interactions (Davis, 2009;Gentili et al, 2016;Mazik, 2012;Park et al, 2015). Although promising, these molecules tend to suffer from a lack of potency in water, a low selectivity among carbohydrates, or both.…”

Molecular Engineering of Carbohydrate Recognition

“…For receptors falling out of these two types, please see the noted reviews. [31,[36][37][38] Under the category of covalent receptors, temple-shaped receptors and flexible receptors differ on the basis of their use of preorganization and structural rigidity. Inspired by the structural characteristics of D-glucose and single crystal structures of lectins, temple-shaped receptors (Figure 3) were designed to recognize all-equatorial D-glucose or D-glucosides.…”

“…[80] Roelens and co-workers have used persubstituted benzene (PSB) rings to construct various tripodal carbohydrate receptors, with efforts specifically for binding β-mannose, and showed that the aminopyrrolic tripodal receptors exhibited remarkable biological activity including antiviral function. [38,55] Due to the steric gearing, the PSB scaffold exhibits facial segregation of the respective substituents around the phenyl plane. [81] This unique stereochemical characteristic led to the development of tripodal receptors that bind certain carbohydrates without all-equatorial hydroxyl groups through the combination of hydrogen bond donors/acceptors as well as potential CH-π interactions for saccharide-aromatic stacking.…”

Biomimetic Carbohydrate‐Binding Agents (CBAs): Binding Affinities and Biological Activities

“…This strategy is extremely valuable for elucidation of the requirements for molecular recognition of carbohydrates and facilitates structure optimisation to achieve the appropriate geometry and functional group disposition for establishing effective binding interactions. A pragmatic user's guide in the nontrivial task of designing effective biomimetic CBAs was recently published by our group; nevertheless, some basic and general concepts in molecular recognition of carbohydrates are summarised here.…”