Importance of Chemical Synthesis for Oligosaccharide Manufacture

Natural carbohydrates composed of 3-10 monosaccharide units in a linear or branched structure connected by α- and/or β-glycosidic bonds are defined as oligosaccharides. Oligosaccharides have complex structures and, as ubiquitous biopolymers in life, are considered to play important roles in various biological systems and signal recognition processes. These important roles of oligosaccharides make them the focus of life science.

Oligosaccharides have the functions of anticancer, antibacterial, anti-inflammatory, antiviral, and enhancing human immune regulation. The synthesis of oligosaccharides is crucial in the medical field. However, obtaining a homogeneous sample during glycosylation is a challenge, and chemical synthesis is an effective solution.

Fig.1 Strategy for the synthesis of oligohomoxylans. (Kinnaert, et al., 2017)

Chemical Synthesis Services at CD BioGlyco

As an expert in the field of glycoscience, CD BioGlyco provides clients with high-quality One-Stop Solutions for Carbohydrate Manufacture. We offer one of the Physical-/Chemical Processes for Oligosaccharide Manufacture-chemical synthesis to manufacture a variety of oligosaccharides, including but not limited to lactulose, Xylogalacturonan, raffinose oligosaccharides, α-(1→2)-linked oligosaccharides, and glucoligosaccharides. In addition, we offer the alkaline isomerization pathway for oligosaccharide production. For chemical synthesis, we propose the following strategies.

• Selective protecting group

Depending on the mechanism, glycosylation occurs in a trans- or cis-selective manner between C-1 and C-2 substituents. Among numerous parameters (e.g., nucleophilicity of the acceptor), the protecting group has the greatest influence on the stereochemistry of glycosylation. Formation of the 1,2-trans glycosidic bond is usually controlled spatially through the participation of the five-membered ring neighboring group of the 2-O-acetyl-protected glycosyl donor. Auxiliary groups located in distal positions (e.g., C-3, C-4, C-5, etc.) have an effect on stereoselectivity during glycosylation.

• Metal-catalyzed glycosylation reaction

Metal-catalyzed glycosylation reactions are used for the production of oligosaccharides. Catalyzed gold(I) yields a new pro-alkynyl gold(I) catalyst using glycosyl O-alkynyl benzoates as donors. This new catalyst is widely used in the synthesis of most glycosidic bonds.

• Non-metal-catalyzed glycosylation reaction

In addition to metal-catalyzed methods, there are also non-metal-catalyzed methods. Using diaryl boronic acid as a catalyst, the glycosyl methanesulfonate donor and partially protected glycopyranoside and furanoside acceptors undergo regioselective and stereoselective coupling, and β-glycosidic structures are selectively accessed through the mechanism of conjugation.

• One-pot glycosylation reaction

For the synthesis of oligosaccharides, one-pot glycosylation is an important method to improve the overall efficiency of the synthesis by minimizing the number of steps and eliminating post-treatment and purification procedures.

• Solid-phase glycosylation reaction

Solid-phase synthesis is another effective method for accelerating oligosaccharide preparation not only by automating the reaction process but also by reacting without the need to purify reaction intermediates. Automated glycan assembly is mainly used for the synthesis of trans-glycosidic bonds, where C2 is involved in the protecting group to ensure stereoselective coupling. Since the generation of the cis-configuration cannot depend on the involvement of C-2, a variety of cis-containing glycosides are successfully obtained using monosaccharides containing remotely involved protecting groups (acetyl or benzoate) as oligosaccharides linked by automated glycan assembly building blocks.

Fig.2 Strategies for chemical synthesis. (CD BioGlyco)

Applications

• Medicinal chemistry and drug development: Scientists design and produce structurally precise oligosaccharides that mimic specific glycan motifs found on cell surfaces. These synthetic oligosaccharides serve as valuable tools to study glycan-protein interactions, facilitating the discovery of novel therapeutic targets and the development of glycan-based drugs.
• Vaccine design: By creating synthetic oligosaccharide antigens that mimic the surface structures of pathogens, researchers induce targeted immune responses.
• Glycobiology research: Chemical synthesis methods enable the production of well-defined oligosaccharide structures for fundamental glycobiology research.

Advantages

• Chemically synthesized oligosaccharides are homogeneous, which overcomes the disadvantages of low yield and purity of isolated oligosaccharides.
• Chemical synthesis is relatively controllable in terms of stereoselectivity and regioselectivity during glycosidic bond formation.
• A professional oligosaccharide manufacturing team.

Scientists at CD BioGlyco have many years of experience in Oligosaccharide Manufacture. With our various advanced technology platforms, we provide clients with strong support for the chemical synthesis of oligosaccharides. For any additional information, please don't hesitate to contact us.

• Supercritical Treatment
• Chemical Hydrolysis