Advances in the Chemical Synthesis of Carbohydrates and Glycoconjugates
Carbohydrates are functional and structural biomolecules with structures ranging from monosaccharides to polysaccharides. They are naturally found as pure glycans or attached to lipids and proteins forming glycoconjugates. The biosynthesis of carbohydrate
- PDF / 1,336,604 Bytes
- 28 Pages / 439.37 x 666.142 pts Page_size
- 91 Downloads / 186 Views
Advances in the Chemical Synthesis of Carbohydrates and Glycoconjugates Ankita Malik, Peter H. Seeberger, and Daniel Varón Silva
Contents 1 Chemical Synthesis of Oligosaccharides 2 Synthesis of Building Blocks 2.1 Glycosylation Reactions and Stereoselectivity 3 Assembly of Oligosaccharides 4 Solution-Phase Synthesis of Glycans 4.1 Modification of Glycans 4.2 Removal of the Protecting Groups, Final Deprotection 4.3 Solid-Phase Synthesis of Oligosaccharides 4.4 Automated Assembly of Oligosaccharides 5 Synthesis of Glycoconjugates 5.1 Synthesis of Neoglycoconjugates 5.2 Synthesis of Natural Glycoconjugates 6 Glycolipids and Amphiphilic Glycoconjugates 7 Conclusions and Outlook References
Abstract Carbohydrates are functional and structural biomolecules with structures ranging from monosaccharides to polysaccharides. They are naturally found as pure glycans or attached to lipids and proteins forming glycoconjugates. The biosynthesis of carbohydrates is not genetically controlled. The regulation takes place by the expression of enzymes that transfer and hydrolyze the glycan units, leading to glycocojugates having complex mixtures of glycan structures. Chemical synthesis emerged as the best strategy to obtain defined glycan and glycoconjugates and overcome the challenging purification processes. Here, we review the recent advances in the synthesis of oligosaccharides using manual and automated methods.
A. Malik, P. H. Seeberger, and D. Varón Silva (*) Max Planck Institute of Colloids and Interfaces, Biomolecular Systems, Potsdam, Germany Department of Chemistry and Biochemistry, Freie Universität Berlin, Berlin, Germany e-mail: [email protected]
A. Malik et al.
The chapter covers the methods for the preparation of building blocks and control of stereoselectivity and regioselectivity during glycosylations. Finally, it also presents the strategies to obtain natural and non-natural glycoconjugates with lipids and proteins. Graphical Abstract
O
HO
O
O
O/N
Glycoconjugates Manual Synthesis HO
O O
O
Oligosaccharide
OR
Neoglycoconjugates HO
Automated Synthesis
O O
O X
Keywords Carbohydrates, Chemical synthesis, Glycoconjugates, Glycoproteins, Glycan modifications Carbohydrates are natural molecules having an important role in the biological processes of cells, as an energy source and structural materials. Carbohydrates are also covalently attached to proteins, peptides, and lipids forming glycoconjugates having different functions and properties [1]. The structure and composition of carbohydrates on glycoconjugates are not genetically controlled and be ranging from monosaccharides to polysaccharides. Glycoconjugates generally contain a heterogeneous mixture of glycans that result from differential expression and activity of the enzymes participating in their biosynthesis and degradation. This heterogeneity hinders the evaluation of defined carbohydrate structures in biological processes. There are no amplification procedures for carbohydrates comparable to the expression of proteins in cell lines or to ampl
Data Loading...
