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Custom Polysaccharide Synthesis

Custom Polysaccharide Synthesis

Overview

Due to the complex structure and the microscopic inhomogeneity of polysaccharides, the synthesis of polysaccharides has long plagued synthetic chemists. CD BioGlyco can provide customers with a custom one-stop polysaccharide synthesis service, According to their research needs, customers can obtain different types and modified polysaccharides. We have confidence to be your essential research assistant in the field of glycobiology.

Key Technologies

Advanced Glycosylation Methods

We utilize highly efficient strategies, including thioglycoside, O-glycoside, and N-pentenyl glycoside donors, to achieve high yields and stereoselectivity. Our methods are optimized for both α- and β-linkages, allowing for precise control over the anomeric configuration, which is critical for natural polysaccharide structures.

Strategic Protecting Group Manipulations

The multi-hydroxyl nature of monosaccharides necessitates careful protecting group strategies to control reactivity and enable selective glycosylation. CD BioGlyco employs a sophisticated toolkit of orthogonal protecting groups (e.g., benzyl, acetyl, pivaloyl, silyl ethers) and leverages modern protecting group manipulations, including photolabile protecting groups, to facilitate efficient and convergent synthesis strategies, especially for highly branched or complex architectures.

Convergent Assembly Strategies

For the synthesis of large and complex polysaccharides, we primarily employ convergent strategies. This involves synthesizing smaller, well-defined oligosaccharide blocks or fragments, which are then coupled together in a highly efficient manner. This modular approach significantly reduces the number of steps and improves overall yields, allowing for the construction of very long polysaccharide chains (e.g., beyond 20 monosaccharide units, and even ultra-long glycans like 92-mer, 100-mer, or 151-mer chains).

Automated Synthesis Platforms

To enhance reproducibility, throughput, and efficiency, we integrate automated solid-phase synthesis techniques where applicable. This technology streamlines the iterative addition of monosaccharide units and simplifies purification, accelerating the delivery of custom polysaccharides.

Background

Polysaccharides are the most abundant biopolymers on earth. They can perform various structural and regulatory functions. Their biological activity depends on the chemical structure, including the composition of monosaccharides, linkages below sugar residues, and the solution conformation. In contrast to polypeptides and polynucleotides, polysaccharides are branched, and each glycosidic bond can form a new stereocenter, which allows only a few monosaccharides to form a variety of different polymers. The construction of polysaccharides through chemical, enzymatic or chemoenzymatic synthesis requires stereo and regional control at each step. For carbohydrates separated as heterogeneous mixtures, synthesis still faces difficulties in detailed molecular understanding.

Due to the important biological functions of polysaccharides, learning the comprehensive definition of their linearity and branching is essential. Many researchers have reported that the chemical modification of polysaccharides significantly increases the diversity of structures, improves biological activity, and even adds new biological activities, including antioxidant and anti-tumor properties, as well as anticoagulant and immunomodulatory activities.

Fig 1. Synthetic Chemistry Laboratory

Unlock the Sugar Code: Synthesized for Science

  • We synthesize diverse polysaccharide architectures, including linear chains and complex branched structures with specific linkage patterns and terminal modifications.
  • From shorter oligosaccharides to ultra-long polysaccharide chains containing dozens or even hundreds of monosaccharide units, our methods are adaptable to varying length requirements.
  • Our expertise allows for the integration of unusual or non-natural monosaccharide residues into the polysaccharide backbone, expanding the functional possibilities of the synthesized glycans.
  • For advanced mechanistic studies or nuclear magnetic resonance (NMR) investigations, we synthesize isotopically labeled polysaccharides, providing invaluable tools for detailed structural and dynamic analyses.
  • Our customized modifications include sulfation, phosphorylation, carboxymethylation, selenization, methylation, acetylation, and other chemical modifications. And many polysaccharides with different labels, such as biotin, fluorescein, and rhodamine, etc.

Workflow

Monomer and Building Block Synthesis

We synthesize or acquire the necessary monosaccharide building blocks, ensuring they are appropriately functionalized and protected for subsequent glycosylation reactions. For complex or rare structures, custom synthesis of these precursors is performed.

Fragment Assembly

For longer polysaccharides, we proceed with the convergent synthesis of smaller oligosaccharide fragments. This involves iterative glycosylation reactions, followed by deprotection and purification steps, to generate well-defined, activated oligosaccharide blocks.

Polysaccharide Elongation and Coupling

The prepared oligosaccharide fragments are then coupled together using highly efficient glycosylation methods to build the desired polysaccharide chain. This step is carefully optimized for maximum yield and minimal side reactions, especially for forming ultra-long glycans.

Deprotection, Purification, and Characterization

Once the full polysaccharide chain is assembled, all temporary protecting groups are selectively removed. The crude product undergoes rigorous purification using advanced chromatographic techniques (e.g., size-exclusion chromatography) to achieve the required purity. Finally, the synthesized polysaccharide is comprehensively characterized using techniques such as mass spectrometry to confirm its exact structure, molecular weight, and purity.

Our workflow. (CD BioGlyco)

Publication Data

DOI.: 10.1021/jacs.0c00751

Journal: Journal of the American Chemical Society

IF: 15.6

Published: 2020

Results: This study achieves a breakthrough in automated polysaccharide synthesis through optimized automated glycan assembly (AGA) on solid phase, enabling unprecedented chain lengths. The authors synthesized a linear 100-mer α-(1→6)-polymannoside via iterative AGA cycles with high stepwise yield (98.75%), alongside a branched 151-mer polymannoside assembled through convergent coupling of AGA-prepared segments—a branched 31-mer acceptor and four 30-mer glycosyl fluoride donors. Critical to this success was the implementation of capping steps to suppress deletion sequences, utilization of a photocleavable linker for efficient product release, employment of AgClO4-activated glycosyl fluoride donors for efficient block couplings, and rigorous real-time high-performance liquid chromatography/matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (HPLC/MALDI-MS) monitoring. Collectively, these advances provide rapid access to structurally defined, ultra-long polysaccharides—previously inaccessible via traditional methods—for probing glycan functions and developing carbohydrate-based materials.

Advantages

  • Our chemical synthesis methodologies provide absolute control over glycosidic bond formation, anomeric configuration, and branching patterns, ensuring the delivery of homogeneous, structurally defined polysaccharides that are impossible to isolate from natural sources.
  • Leveraging cutting-edge convergent strategies and efficient glycosylation methods, we possess the unique capability to synthesize not only complex but also remarkably long polysaccharide chains, including those exceeding 100 monosaccharide units, enabling studies on large polymeric glycans.
  • Our robust synthetic platform allows for the incorporation of a broad spectrum of natural and non-natural monosaccharides, offering unparalleled flexibility in designing and creating novel polysaccharide structures with specific biological or material properties.

Applications

  • Polysaccharides and their derivatives hold immense promise as therapeutic agents (e.g., anticoagulants, anti-inflammatories, antivirals) and drug delivery vehicles.
  • Polysaccharides play a key role in tissue engineering, regenerative medicine, and drug delivery systems, where their excellent biocompatibility and biodegradability make them ideal materials for developing hydrogels, scaffolds, and coatings.
  • Understanding and manipulating the structure of dietary polysaccharides is important for researching functional foods and nutraceuticals with beneficial effects on gut health, immunity, and metabolic regulation.

Associated Services

(AI-CD BioGlyco)

Custom polysaccharide synthesis provides the essential foundation of precisely engineered carbohydrate polymers. This capability directly enables our Polysaccharide-modified Nanoparticle Production Service, where these tailored polysaccharides are strategically employed to functionalize nanoparticle surfaces, enhancing biocompatibility, targeting, and stability for advanced biomedical and research applications. Furthermore, the versatility of synthetic polysaccharides extends powerfully into material science, underpinning the development of Polysaccharide-based Biodegradable Material for Food Packaging. Here, polysaccharides like chitosan or customized derivatives offer sustainable, non-toxic barrier properties crucial for modern eco-friendly packaging solutions. Finally, the rigorous application of polysaccharide characterization and immunogenicity assessment techniques, core to our synthesis expertise, is vital for our Group A Meningococcal Polysaccharide Vaccine Evaluation Service. This service leverages deep polysaccharide knowledge to critically assess vaccine purity, molecular size, identity, and crucially, immunological potency for safety and efficacy confirmation. Thus, custom synthesis serves as the cornerstone for diverse, high-impact applications spanning nanotechnology, sustainable materials, and life-saving vaccine development.

Frequently Asked Questions

CD BioGlyco has numerous successful experiences in the custom synthesis of polysaccharides. Our well-trained researchers and the most advanced facilities can provide customers with higher-quality synthesis services to help customers explore polysaccharides faster and more comprehensively.

Customers can contact our employees directly and we will respond promptly. If you are interested in our services, please contact us for more detailed information.

Reference

  1. Joseph, A.A.; et al. Total synthesis of polysaccharides by automated glycan assembly. Journal of the American Chemical Society. 2020, 142(19): 8561-8564. (CCBY)
This service is for Research Use Only, not intended for any clinical use.
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CD BioGlyco is a world-class biotechnology company with offices in many countries. Our products and services provide a viable option to what is otherwise available.

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