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Custom Carbohydrate Antigen Synthesis

Overview

Having worked with carbohydrate antigens for many years, CD BioGlyco can customize its synthesis according to customers' research needs. We have confidence to be your essential research assistant in the field of glycobiology.

Background

On the surface of cancer cells, abnormal glycosylation occurs, including glycan truncation, neo-glycan expression, and increase/decrease in glycan epitope density. A common aberration in adenocarcinoma is an over-simplification of mucins' glycosylation pattern. Mucins are highly glycosylated proteins and a key component of mucus and other biological lubricants. The tumor-associated carbohydrate antigen (TACA) is a family of oligosaccharides, a subclass of which is expressed on mucin glycopeptides in cancer. ACA can be divided into three categories: the mucin-based glycopeptides (Tn, sialyl-Tn, and TF), lactosamine series expressed as glycoproteins and glycolipids (sialyl Lewis^x, Lewis^x, sialyl Lewis^A, and Lewis^Y), and truncated gangliosides (Globo-H, stage-specific embryonic antigen 3, and ganglioside monosialic 2).

The first category has attracted attention due to its relative simplicity and exclusivity to cancer. Although the second category may be used as vaccine targets, their structural complexity limits their use as synthetic vaccines. Gangliosides have shown great potential and may become a rich source of immunological targets in the future. For decades, compared with traditional therapies (chemotherapy and radiotherapy), cancer immunotherapy has great advantages, which has opened the way for the development of TACA molecular design, thereby promoting the development of specific therapies for cancer.

Key Technologies

Advanced Chemical Glycosylation

We deploy intricate synthetic tactics integrating multicomponent single-vessel assembly to forge elaborate oligosaccharide frameworks. This paradigm enables accelerated construction of convoluted glycan antigens, frequently exhibiting superior assembly fidelity versus incremental methodologies. Mastery over stereochemical governance—notoriously demanding in saccharide synthesis—guarantees rigorous α/β anomeric configuration. Our designs incorporate building blocks exhibiting orthogonally reactive handles, permitting donor-specific activation for regimented glycosylation.

Chemo-Enzymatic Synthesis

Conjugating enzymatic precision with synthetic plasticity, our dual-strategy paradigm offers potent avenues to intricate epitopes. Such convergent tactics facilitate gram-scale, cost-efficient production of antigens like Neu5Gc from glucose precursors. This approach excels in delivering pristine antigens for in vitro and in vivo interrogation, circumventing heterogeneity constraints.

Protective Group Strategies

Our mastery of protective group chemistry is fundamental to navigating the multi-functional nature of carbohydrates. We strategically apply and remove protecting groups to ensure selective reactions and prevent undesired side products, optimizing the overall synthesis yield and purity.

Services

CD BioGlyco has successfully developed several effective strategies to synthesize different types of carbohydrate antigens. The synthesized carbohydrate antigens are verified by nuclear magnetic resonance (NMR) and glycan microarray analysis. And for the shortcomings of low immunogenicity and low metabolic stability of synthetic antigens, we have developed different optimization strategies:

Co-administer the vaccine with adjuvants.
Conjugation of the selected TACA with immunogenic carriers (such as KLH, Ova, BSA).
Our synthetic chemists design TACA analogs that are resistant to hydrolysis to avoid being hydrolyzed by endogenous glycosidases.

Workflow

Synthesis Strategy Development

Based on the target structure, our scientists design a tailored synthesis strategy, selecting the most appropriate chemical and/or chemo-enzymatic methodologies. This involves careful planning of building blocks, protective group schemes, and reaction conditions to optimize efficiency and yield.

Intermediate Synthesis & Purification

Individual monosaccharide building blocks and key disaccharide/oligosaccharide intermediates are synthesized and meticulously purified to ensure high-quality starting materials for the subsequent coupling steps.

Glycosylation & Elongation

The core of the synthesis involves the strategic coupling of saccharide units through glycosylation reactions. This iterative process builds the target carbohydrate antigen step-by-step, with careful monitoring and optimization at each stage to achieve the desired stereochemistry and yield.

Deprotection & Final Purification

Once the complete carbohydrate antigen backbone is formed, all temporary protective groups are selectively removed. The crude product then undergoes comprehensive purification using advanced chromatographic techniques to isolate the target molecule with high purity.

Quality Control & Characterization

The purified carbohydrate antigen undergoes stringent quality control analysis using a suite of analytical tools to confirm its identity, purity, and structural integrity. A detailed certificate of analysis is provided, ensuring full transparency and confidence in the delivered product.

Our workflow. (CD BioGlyco)

Publication Data

DOI.: 10.1021/acs.orglett.5c01560

Journal: Organic Letters

IF: 5.0

Published: 2025

Results: The authors developed a highly stereoselective, iron-catalyzed method for synthesizing biologically important Tn antigens (O-linked GalNAc-Ser/Thr glycopeptides) on a multigram scale. This novel glycal 1,2-cis-aminoglycosylation reaction uses an iron catalyst to enable exclusive α-selectivity across diverse galactosyl donors (e.g., 3,4-di-O-acetyl-6-O-TBS-D-galactal and tri-O-acetyl-D-galactal) and amino acid acceptors (Ser/Thr with various N-protecting groups), overcoming previous limitations in stereocontrol and substrate scope. The method was optimized to minimize side reactions and scaled efficiently (up to 20 mmol). Post-glycosylation transformations were streamlined using rapid deprotection sequences (e.g., HCl-mediated N-Boc removal, hydrogenolysis, methanolysis) to deliver single-diastereomer Tn antigens (1a/1b) and N-Fmoc-protected building blocks (16a/16b) in high yields, providing a practical route for glycobiology research and glycopeptide synthesis.

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

Vaccine development: Design and synthesis of carbohydrate-based vaccines against infectious diseases and cancer, leveraging their immunogenic properties.
Cancer research: Investigation of tumor-associated carbohydrate antigens as biomarkers for cancer diagnosis, prognosis, and targets for novel immunotherapies.
Infectious disease research: Study of pathogen-host interactions, development of diagnostic assays, and discovery of anti-infective agents targeting microbial carbohydrate structures.
Glycobiology & immunology: Elucidation of the roles of glycans in cellular communication, immune recognition, inflammation, and autoimmune diseases.
Drug discovery & development: Identification of novel therapeutic targets and development of carbohydrate-mimetic drugs.

Associated Services

(AI-CD BioGlyco)

Our custom carbohydrate antigen synthesis technology empowers the creation of standardized, pathogen-specific antigens with critical fidelity, particularly for bacterial polysaccharides where glycan microheterogeneity dictates immunogenic potency. As a direct extension of this capability, we offer specialized production services for high-priority pathogens.

Frequently Asked Questions

CD BioGlyco can customize different experimental programs to meet the different research needs of customs. The optimized methods we adopted can solve most of the shortcomings of synthetic carbohydrate antigens and provide the best quality products for customers' research.

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

Yin, L.; et al. Stereoselective multigram-scale Tn antigen synthesis via the iron-catalyzed Glycal 1, 2-cis-aminoglycosylation. Organic Letters. 2025. (Open Access)

This service is for Research Use Only, not intended for any clinical use.