Glycopeptides are essential components of cells, viruses and bacteria and are involved in recognition events and the immune response. Glycoproteins are candidates for vaccines,1 therapeutics and diagnostics.
The synthesis of O- and N-linked glycopeptides relies on either extensive solution phase synthesis of the glycosylated amino acid2 before incorporation to the peptide or on enzymatic elongation of the glycan after peptide elongation.3 The above methods are not approachable to most of the biology community that cannot prepare glycosylated amino acid by manual synthesis.
Herein, we describe a straightforward, automated synthesis of O-linked glycopeptides. The automated glycopeptides synthesis combines both automated solid phase peptide and oligosaccharide synthesis.4 Similar to the synthesis of peptides and oligonucleotides, the described method requires minimal manual intervention, and can be performed with only minor training in chemistry.
Adopting the automated approach could increase the limited library of investigated glycopeptides, and therefore, will allow better understanding of the involvement of these highly relevant biomolecules in natural- and disease-related biological mechanisms.
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References:
[1] Allen, J. R.; Harris, C. R.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 1890-7.
[2] Kaifu, R.; Osawa, T. Carb. Res. 1977, 58, 235-239.
[3] Koeller, K. M.; Smith, M. E. B.; Wong, C. H. J. Am. Chem. Soc. 2000, 122, 742-743.
[4] Kröck, L.; Esposito, D.; Castagner, B.; Wang, C. C.; Bindschädler, P.; Seeberger, P. H.; Chem. Sci., 2012, 3, 1617-1622.
