Selected Research Topics of the Dondoni Group over the Last Two Decades (2000–2020)

Abstract

From a selection of research topics carried out in our laboratory during the last twenty years it becomes apparent that our main target was the discovery of new or improved synthetic methods together with new properties. Our efforts were made with the aim of being of some utility to other fields of research, with particular emphasis to glycobiology and heterocyle-based bioorganic chemistry. We performed new chemistry mainly in the field of carbohydrate manipulations taking as a primary rule the simplicity and efficiency manners. Toward this end, modern synthetic tools and approaches were employed such as heterocyle-based transformations, multicomponent reactions, organocatalysis, click azide–alkyne cycloadditions, reactions in ionic liquids, click photoinduced thiol-ene coupling, and click sulfur–fluoride exchange chemistry. With these potent methodologies in hand, the syntheses of carbohydrate containing amino acids up to proteins glycosylation were performed.1 Heterocyclic Glycoconjugates and Amino Acids2 Triazole-Linked Oligonucleotides: Application of Click CuAAC3 Non-Natural Glycosyl Amino Acids4 Non-Natural Oligosaccharides5 Calixarene-Based Glycoclusters6 Carbohydrate-Based Building Blocks7 Homoazasugars and Aza-C-disaccharides8 Synthesis of Glycodendrimers9 Peptide and Protein Glycoconjugates10 Conclusions

Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications

“…Earlier, covalent modification at the surface of magnetic nanoparticles (MNPs) either by amide bond formation or Cu­(I)-catalyzed 1,2,3-triazole forming reaction was executed to generate novel glyconanoparticles. The azide functionality on the surface of magnetic nanoparticles facilitated better conjugation potential with alkynated scaffolds. , Triazole-linked calix[4]­arene scaffold O -glycosides have been synthesized by the Dondoni–Marra group, and this solved the obstacle of immobilization of glycosides on a TiO 2 nanoparticle surface. These have been developed from functionalized (azido and carboxyl) calix[4]­arene scaffolds followed by their immobilization on TiO 2 nanoparticles with the carbohydrates being strongly adhered to the TiO 2 surface. − This variety of hybrid materials (i.e., glyconanoparticles) makes a good biomimetic model of saccharide display at the cell surface.…”

“…The azide functionality on the surface of magnetic nanoparticles facilitated better conjugation potential with alkynated scaffolds. , Triazole-linked calix[4]­arene scaffold O -glycosides have been synthesized by the Dondoni–Marra group, and this solved the obstacle of immobilization of glycosides on a TiO 2 nanoparticle surface. These have been developed from functionalized (azido and carboxyl) calix[4]­arene scaffolds followed by their immobilization on TiO 2 nanoparticles with the carbohydrates being strongly adhered to the TiO 2 surface. − This variety of hybrid materials (i.e., glyconanoparticles) makes a good biomimetic model of saccharide display at the cell surface. Owing to the presence of sugar units at the surface, they are susceptible to multivalent interactions such as those taking place in natural ambient conditions .…”

“…These have been developed from functionalized (azido and carboxyl) calix[4]­arene scaffolds followed by their immobilization on TiO 2 nanoparticles with the carbohydrates being strongly adhered to the TiO 2 surface. − This variety of hybrid materials (i.e., glyconanoparticles) makes a good biomimetic model of saccharide display at the cell surface. Owing to the presence of sugar units at the surface, they are susceptible to multivalent interactions such as those taking place in natural ambient conditions . Dondoni and co-workers have explored CuAAC click chemistry and synthesized a glyconanoparticle, 1600 ; for this purpose, calix[4]­arene 1597 was conjoined with TiO 2 in acetone at room temperature to give calixarene-coated TiO 2 nanoparticle 1598 .…”

Fucosylated ubiquitin and orthogonally glycosylated mutant A28C: conceptually new ligands for Burkholderia ambifaria lectin (BambL)

“…The conjugation of Ub-A28C with 13 was efficiently performed by using another classical click reactions namely the photoinduced thiol-ene coupling (TEC) through the formation of a thioether bond. 29 To a solution of Ub-A28C (450 μM in NaPi 150 mM, pH 7.5) were added an excess of 13 and of DPAP as photo-initiator, and the reaction mixture was irradiated at 365 nm. 30 The reaction was monitored by 2D 1 H-15 N HSQC spectra, and reached completion within only 20 minutes.…”

Fucosylated Ubiquitin and Orthogonally Glycosylated Mutant A28C: Conceptually New Ligands for Burkholderia Ambifaria Lectin (BambL)†

“…The conjugation of Ub-A28C with 13 was efficiently performed by using another classical click reactions namely the photoinduced thiol-ene coupling (TEC) through the formation of a thioether bond. 28 To a solution of Ub-A28C (450 μM in NaPi 150 mM, pH 7.5) were added an excess of 13 and of DPAP as photo-initiator, and the reaction mixture was irradiated at 365 nm. 29 The reaction was monitored by 2D 1 H-15 N HSQC spectra, and reached completion within only 20 minutes.…”