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Synthesis of Oligosaccharides and Glycoconjugates

The study provides important information for using these glycosyltransferases as powerful catalysts in enzymatic and chemoenzymatic syntheses of oligosaccharides and derivatives which can be useful probes and reagents.

Chemical and enzymatic synthesis of glycoconjugates …

The study provides important information for using these glycosyltransferases as powerful catalysts in enzymatic and chemoenzymatic syntheses of oligosaccharides and derivatives which can be useful probes and reagents.",}

Review article and products for sialic acid synthesis and signaling.

Synthetic oligosaccharides and glycoconjugates are increasingly used as probes for biological research and as lead compounds for drug and vaccine discovery. These endeavors are, however, complicated by a lack of general methods for the routine preparation of this important class of compounds. Recent development such as one-pot multi-step protecting group manipulations, the use of unified monosaccharide building blocks, the introduction of stereoselective glycosylation protocols, and convergent strategies for oligosaccharide assembly, are beginning to address these problems. Furthermore, oligosaccharide synthesis can be facilitated by chemo-enzymatic methods, which employ a range of glycosyl transferases to modify a synthetic oligosaccharide precursor. Glycosynthases, which are mutant glycosidases, that can readily form glycosidic linkages are addressing a lack of a wide range glycosyltransferases. The power of carbohydrate chemistry is highlighted by an ability to synthesize glycoproteins.

The study provides important information for using these glycosyltransferases as powerful catalysts in enzymatic and chemoenzymatic syntheses of oligosaccharides and derivatives which can be useful probes and reagents.AB - β1-3-N-Acetylglucosaminyltransferases (β3GlcNAcTs) and β1-4-galactosyltransferases (β4GalTs) have been broadly used in enzymatic synthesis of N-acetyllactosamine (LacNAc)-containing oligosaccharides and glycoconjugates including poly-LacNAc, and lacto-N-neotetraose (LNnT) found in the milk of human and other mammals.

Biocatalysis and Biotransformation: Vol 36, No 2

As important biomolecules in living organisms, carbohydrates have received increasing attention in recent years. Their important roles in biologic events are being continuously unraveled. The development of synthetic methodologies, including both chemical and enzymatic methods, contributes greatly to the advance of the field of glycoscience. The involvement of regio- and stereo-selective enzymes in the synthesis of complex carbohydrate-containing molecules has become an indispensable approach. Many enzymes involved in the biosynthesis and biodegradation of carbohydrates have been characterized and have been applied for the production of carbohydrate-containing biomolecules, including oligosaccharides, polysaccharides, glycoproteins, glycolipids, and glycosylated natural products. A range of strategies for enzymatic synthesis have also been developed, such as protein engineering of glycosidases and glycosyltransferases by site-directed mutagenesis or directed evolution, one-pot multiple-enzyme synthesis, sugar nucleotide regeneration, solid-phase enzymatic synthesis, synthesis using immobilized enzymes, and cell-based synthesis. Enzymatic synthesis will continue to play critical roles in obtaining complex carbohydrate-containing biomolecules. Future efforts should focus on identifying synthetically useful enzymes such as those with flexible or novel substrate specificity and those that can form new bonds. This identification can be achieved by functional genomics and mutagenesis studies. Development of novel enzymatic synthetic methods is also critical to access diverse naturally occurring and non-natural derivatives of carbohydrates and glycoconjugates.

Oligosaccharides involved in glycoconjugates play important roles in a number of biological events. To elucidate the biological functions of oligosaccharides, sufficient quantities of structurally defined oligosaccharides, are of limited availability by traditional purification methods, are required. Hence, chemical and enzymatic syntheses of oligosaccharides are becoming increasingly important in glycobiology and glycotechnology. In addition, oligosaccharides often occur as glycoconjugates attached to proteins or lipids. Hence, the development of simple and effective methods for synthesizing neoglycoconjugates such as neoglycoprotein and neoglycolipids is essential for an understanding of the biological function of these molecules. Here we review the most recent developments in the enzymatic synthesis of oligosaccharides and neoglycoconjugates.

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