Carbohydrates for Click Chemistry

Protein and lipid glycosilation is a life-governing and omnipresent process. Glycoconjugates display a multitude of biological effects from protein folding and stabilization, energy storage, cell surface interaction through molecular recognition motifs for cell-cell communication, and structural support and protection. Defective metabolic pathways in pathological processes, inflammation and microbial virulence, neurodegenerative conditions or tumour metastasis are only a few key words indicating the many possible application fields. The smooth and selective reaction conditions of the Click reaction open so far impossible molecule design for drug development and vaccine development based on carbohydrate conjugation.

General References:

• Essentials of Glycobiology; A. Varki, R. Cummins, J. Esko, H. Freeze, G. Hart and J. Marth; Cold Spring Harbor Laboratory Press; Cold Spring Harbor 1999. Role of glycosylation in development; R. S. Haltiwanger and J. B. Lowe; Annu Rev Biochem 2004; 73, 491-537.
• Glycosylation and the immune system; P. M. Rudd, T. Elliott, P. Cresswell, I. A. Wilson and R. A. Dwek; Science 2001; 291, 2370-6. Glycosylation in cellular mechanisms of health and disease; K. Ohtsubo and J. D. Marth; Cell 2006; 126, 855-67.
• The role of selectins in inflammation and disease; K. Ley; Trends Mol Med 2003; 9, 263-8.
• Carbohydrate diversity: synthesis of glycoconjugates and complex carbohydrates; A. Holemann and P. H. Seeberger; Curr Opin Biotechnol 2004; 15, 615-22.
• Post-translational modifications in the context of therapeutic proteins; G. Walsh and R. Jefferis; Nat Biotechnol 2006; 24, 1241-52.
• Glycomics: a pathway to a class of new and improved therapeutics; Z. Shriver, S. Raguram and R. Sasisekharan; Nat Rev Drug Discov 2004; 3, 863-73.
• The bittersweet promise of glycobiology; A. Dove; Nat Biotechnol 2001; 19, 913-7.
• Carbohydrate and protein immobilization onto solid surfaces by sequential Diels-Alder and azide-alkyne cycloadditions; X. L. Sun, C. L. Stabler, C. S. Cazalis and E. L. Chaikof; Bioconjug Chem 2006; 17, 52-7.
• Covalent display of oligosaccharide arrays in microtiter plates; M. C. Bryan, F. Fazio, H. K. Lee, C. Y. Huang, A. Chang, M. D. Best, D. A. Calarese, O. Blixt, J. C. Paulson, D. Burton, I. A. Wilson and C. H. Wong; J Am Chem Soc 2004; 126, 8640-1.
• Multivalent, bifunctional dendrimers prepared by click chemistry; P. Wu, M. Malkoch, J. N. Hunt, R. Vestberg, E. Kaltgrad, M. G. Finn, V. V. Fokin, K. B. Sharpless and C. J. Hawker; Chem Commun (Camb) 2005, 5775-7.
• A chemoenzymatic approach to glycopeptide antibiotics; H. Lin and C. T. Walsh; J Am Chem Soc 2004; 126, 13998-4003.