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 Acids

2 Triazole-Linked Oligonucleotides: Application of Click CuAAC

3 Non-Natural Glycosyl Amino Acids

4 Non-Natural Oligosaccharides

5 Calixarene-Based Glycoclusters

6 Carbohydrate-Based Building Blocks

7 Homoazasugars and Aza-C-disaccharides

8 Synthesis of Glycodendrimers

9 Peptide and Protein Glycoconjugates

10 Conclusions

Key words

glycosyl amino acids - glycosylated calixarenes - glycosylated proteins - glycosylated dendrimers - SuFEx - thiol–ene coupling

• References

• 1 Dondoni A, Massi A. Mol. Diversity 2003; 6: 261
• 2 Dondoni A, Massi A, Sabbatini S. Tetrahedron Lett. 2002; 43: 5913
• 3 Dondoni A, Massi A, Sabbatini S, Bertolasi V. J. Org. Chem. 2002; 67: 6979
• 4 Dondoni A, Massi A, Sabbatini S, Bertolasi V. Adv. Synth. Catal. 2004; 346: 1355
• 5 Dondoni A, Massi A, Minghini E, Bertolasi V. Tetrahedron 2004; 60: 2311
• 6 Nuzzi A, Massi A, Dondoni A. QSAR Comb. Sci. 2007; 26: 1191
• 7 Nuzzi A, Massi A, Dondoni A. Org. Lett. 2008; 10: 4485
• 8 Dondoni A, Giovannini PP, Massi A. Org. Lett. 2004; 6: 2929
• 9 Dondoni A, Massi A, Aldhoun M. J. Org. Chem. 2007; 72: 7677
• 10 Aldhoun M, Massi A, Dondoni A. J. Org. Chem. 2008; 73: 9565
• 11 Barghash RF, Massi A, Dondoni A. Org. Biomol. Chem. 2009; 7: 3319
• 12 Dondoni A, Massi A, Sabbatini S. Chem. Eur. J. 2005; 11: 7110
• 13 Dondoni A, Marra A, Mizuno M, Giovannini PP. J. Org. Chem. 2002; 67: 4186
• 14 Dondoni A, Marra AA. Tetrahedron Lett. 2003; 44: 4067
• 15 Fiore M, Marra A, Dondoni A. J. Org. Chem. 2009; 74: 4422
• 16 Cheshev P, Marra A, Dondoni A. Org. Biomol. Chem. 2006; 4: 3225
• 17 Lo Conte M, Chambery A, Marra A, Dondoni A. Synlett 2009; 2679
• 18 Dondoni A, Marra AC. J. Org. Chem. 2006; 71: 7546
• 19 Marra A, Moni L, Pazzi D, Corallini A, Bridi D, Dondoni A. Org. Biomol. Chem. 2008; 6: 1396
• 20 Moni L, Rossetti S, Scoponi M, Marra A, Dondoni A. Chem. Commun. 2010; 46: 475
• 21 Dondoni A, Catozzi N, Marra A. J. Org. Chem. 2004; 69: 5023
• 22 Dondoni A, Marra A. Chem. Rev. 2004; 104: 2557
• 23 Dondoni A, Catozzi N, Marra A. J. Org. Chem. 2005; 70: 9257
• 24 Massi A, Nuzzi A, Dondoni A. J. Org. Chem. 2007; 72: 10279
• 25 Ducatti DR. B, Massi A, Noseda MD, Duarte ME. R, Dondoni A. Org. Biomol. Chem. 2009; 7: 576
• 26 Dondoni A, Giovannini PP, Perrone D. J. Org. Chem. 2002; 67: 7203
• 27 Dondoni A, Nuzzi A. J. Org. Chem. 2006; 71: 7574
• 28a Dondoni A. Angew. Chem. Int. Ed. 2008; 47: 8995
• 28b Hoyle CE, Bowman CN. Angew. Chem. Int. Ed. 2010; 49: 1540
• 29 Chabre YM, Roy R. Curr. Top. Med. Chem. 2008; 8: 1237
• 30 Lo Conte M, Robb MJ, Hed Y, Marra A, Malkoch M, Hawker CJ, Dondoni A. J. Polym. Sci., Part A: Polym. Chem. 2011; 49: 4468
• 31 Ghirardello M, Oberg K, Staderini S, Renaudet O, Berthet N, Dumy P, Hed Y, Marra A, Malkoch M, Dondoni A. J. Polym. Sci., Part A: Polym. Chem. 2014; 52: 2422
• 32 Dondoni A, Massi A, Nanni P, Roda A. Chem Eur. J. 2009; 15: 11444
• 33 Marra A, Dong J, Ma T, Luchinat C, Fragai M, Nativi C, Dondoni A. Chem Eur. J. 2018; 24: 18981
• 34 Dong J, Krasnova L, Finn MG, Sharpless KB. Angew. Chem. Int. Ed. 2014; 53: 9430
• 35 Marra A, Nativi C, Dondoni A. New J. Chem. 2020; 44: 4678