Abstract
Protein glycosylation has dramatically enriched both the functional and structural diversity of proteins in mammals. Due to the non-template biosynthesis of glycoproteins in the nature, glycoproteins always exist as heterogeneous mixtures with different glycan structures, which have complicated the isolation of pure and well-defined glycoforms for detailed mechanistic and functional studies. Over the past years, different strategies including chemical and chemoenzymatic methods have been developed for obtaining the homogenous glycoproteins, which will offer new opportunities to conduct an extensive assessment of relationship between the structure and function of glycoproteins and to reveal the biological role of the individual oligosaccharide on a glycoprotein for the evolution and development of cells. This chapter gives insight into the recent progress in the development of chemical and chemoenzymatic synthesis of homogenous glycoproteins including native chemical ligation, serine/threonine ligation, and chemoenzymatic glycoprotein remodeling. Examples are selected to demonstrate successful applications of synthetic strategies developed so far.
This is a preview of subscription content, log in via an institution.
References
Amin MN, Huang W, Mizanur RM et al (2011) Convergent synthesis of homogeneous Glc1Man9GlcNAc2-protein and derivatives as ligands of molecular chaperones in protein quality control. J Am Chem Soc 133:14404–14417
Dawson PE, Muir TW, Clark-Lewis L et al (1994) Synthesis of proteins by native chemical ligation. Science 266:776–779
Li X, Lam HY, Zhang Y et al (2010) Salicylaldehyde ester-induced chemoselective peptide ligations: enabling generation of natural peptidic linkages at the serine/threonine sites. Org Lett 12:1724–1727
Murakami M, Okamoto R, Izumi M et al (2012) Chemical synthesis of an erythropoietin glycoform containing a complex-type disialyloligosaccharide. Angew Chem Int Ed 51:3567–3572
Piontek C, Ring P, Harjes O et al (2009a) Semisynthesis of a homogeneous glycoprotein enzyme: ribonuclease C: part 1. Angew Chem Int Ed 48:1936–1940
Piontek C, Silva DV, Heinlein C et al (2009b) Semisynthesis of a homogeneous glycoprotein enzyme: ribonuclease C: part 2. Angew Chem Int Ed 48:1941–1945
Rademacher TW, Parekh RB, Dwek RA (1988) Glycobiology. Ann Rev Biochem 57:785–838
Wan Q, Danishefsky SJ (2007) Free-radical-based, specific desulfurization of cysteine: a powerful advance in the synthesis of polypeptides and glycopolypeptides. Angew Chem Int Ed 46:9248–9252
Wang P, Dong S, Shieh J et al (2013) Erythropoietin derived by chemical synthesis. Science 342:1357–1360
Xu C, Lam HY, Zhang Y et al (2013) Convergent synthesis of MUC1 glycopeptides via serine ligation. Chem Comm 49:6200–6202
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer Japan
About this entry
Cite this entry
Xu, C., Li, X. (2014). Glycopeptide/Glycoprotein Synthesis. In: Endo, T., Seeberger, P., Hart, G., Wong, CH., Taniguchi, N. (eds) Glycoscience: Biology and Medicine. Springer, Tokyo. https://doi.org/10.1007/978-4-431-54836-2_30-1
Download citation
DOI: https://doi.org/10.1007/978-4-431-54836-2_30-1
Received:
Accepted:
Published:
Publisher Name: Springer, Tokyo
Online ISBN: 978-4-431-54836-2
eBook Packages: Springer Reference Biomedicine and Life SciencesReference Module Biomedical and Life Sciences