Chiral self-assembly of lactose functionalized perylene bisimides as multivalent glycoclusters

Abstract

A chiral self-assembly has been constructed from a d-lactose functionalized perylene bisimide derivative, showing right-handed supramolecular stacking induced by the chiral d-lactose moieties. Benefiting from the grafting of D-lactose, the self-assembled multivalent glycoclusters exhibited specific binding with PNA lectin.

Perylene Bisimide Dye Assemblies as Archetype Functional Supramolecular Materials

“…337 solvent-dependent chiroptical inversion was reported for selfassembly systems of a PBI derivative bearing six D-mannoses in different DMSO/water mixtures, 340 whereas a PBI derivative functionalized with two D-lactoses exhibited only right-handed supramolecular stacking in different volume ratios of DMSO/ water. 341 Noteworthy is that temperature-dependent transformation of supramolecular nanostructures from twisted ribbons to microplates of a core-tetrachlorinated PBI containing glucose units in imide positions was achieved by modulation of the interaction of glucose moieties. 342 In a very comprehensive study, Frauenrath and co-workers demonstrated the self-assembly of oligopeptide-substituted PBI 4-12 into well-ordered nanofibrils ( Figure 40).…”

Fluorescent glycoconjugates and their applications

“…Besides the binding properties of PDI-based glycoconjugates to lectins and cells, some studies focused on their self-assembly physico-chemical properties in water. Chiral helical selfassembly of lactosylated PDI-based glycoclusters 67 provided right-handed helical supramolecular structure held together through - stacking generating modified fluorescence emis- sion. The resulting multivalent helical supramolecular glycoconjugate exhibited specific binding with PNA through its lactoside epitopes ( Figure 16) while ConA and BSA had no binding.…”

An Improved Protocol for the Synthesis and Purification of Yariv Reagents

“…It is worth noting here that many other amphiphilic glycoconjugates exhibit similar challenges with respect to resolving -OH resonances clearly, and in several cases where -OH resonances are well-resolved, the product was isolated from methanol. [13][14][15][16] Finally, several additional Yariv reagents were synthesized, isolated and purified using the optimized procedures. These advances allowed full characterization of these Yariv reagents for the first time.…”