Alginate-based Mimetic Development Service

Alginate is a group of Polysaccharides derived from the cell wall of brown algae, consisting of β-D-mannuronic (M) and α-L-guluronic acids (G) connected by 1,4 glycosidic bonds. It is widely used in drug development and disease treatment research due to its rich and diverse biological activities. CD BioGlyco has been engaged in Marine Carbohydrate Mimetic development services for many years, combined with an experienced synthetic team to design functional characterization structures to accelerate the project progress of clients.

Fig.1 Structural composition of the alginate and their oligomers. (Wang, et al., 2021)

Alginate-based Mimetic Development Service at CD BioGlyco

The structural features of alginate have direct effects on its biological functions and mechanism of action, for example, molecular size, G/M ratio, and terminal structure. Depending on the different structural properties of alginate, our researchers provide two strategies applied to mimic synthesis.

Chemical Synthesis Service

• The synthesis of alginate-based mimetic through the post-glycosylation oxidation strategy: Our researchers use trifluoromethane sulfonic anhydride (Tf2O) to preactivate sulfoxide to form a potent donor of β-mannoside. The reaction can be quickly completed by the bimolecular nucleophilic substitution reaction.
• The synthesis of alginate-based mimetic through the pre-glycosylation oxidation strategy: Our synthetic route not only synthesized β-magnonic acid by post-glycosylation oxidation, but the carboxylic acid in the building blocks has also been directly used to assemble alginate oligosaccharides. Fast and accurate synthesis of targets through an automated solid-phase assembly system. Moreover, based on the β-guided mannuronate protocol, we provide clients with the design and synthesis services for long-chain mimics through multi-step coupling.

Other Service

Obtaining structurally well-defined alginate-based mimetics is crucial to studying its biological activity. For the synthetic target, combined with perfect experimental equipment, leading analysts provide comprehensive identification services for clients. In addition, we provide disease models and animal activity assay services, combined with clients' requirements, to provide customized services.

Fig.2 Flow chart of alginate-based mimetic development service. (CD BioGlyco)

Publication

Technology: Nuclear magnetic resonance (NMR), Liquid chromatograph mass spectrometer

Journal: Angewandte Chemie International Edition in English

Published: 2012

IF: 16.6

Results: In this study, the synthesis of mannuronic acid alginate with 1,2-cis-glycosidic bonds was automated by an automated solid-phase assembly system. This system ensures the stereoselective formation of β-mannose bonds and allows rapid evaluation of structural features without the need for purification and isolation steps of intermediates. The product quantity not only meets the requirements of bioactivity testing but also has high purity, quickly using nuclear magnetic resonance (NMR) to verify the structure of the compound. Analysis of the crude reaction mixture by chromatography/mass spectrometry revealed a high coupling efficiency. The NMR profiles demonstrated a superior stereoselectivity for the coupling reaction. The target object has regular structural features, and the glycosidic bond reasonably introduces β-stereoselectivity.

Fig.3 Detection map of various indicators of pure product 7. (Walvoort, et al., 2012)

Applications of Alginate-based Mimetic

• Alginate-based mimetics are exploited either as drug carriers or as hydrogels.
• Alginate-based mimetics can be used to prepare biomedical materials by multiple cross-linking methods, for example, divalent cation-mediated gelation, such as Ca²⁺.
• Alginate-based mimetics are used in the research of cardiovascular-related disease treatment and prevention.
• Alginate-based mimetics plays a role in the treatment of chronic renal failure. Furthermore, oligomeric alginate-based mimics are thought to play a role in diabetes treatment.
• When alginate-based mimetics are used as therapeutic adjuvants, drug carriers, wound-healing materials, and biological scaffolds, they improve the study of antitumor immune effects in ovarian cancer, melanoma, liver cancer, and breast cancer.
• Alginate-based mimetics regulate human gut microbiota and promote the efficacy of traditional drugs as therapeutic agents or drug carriers.
• In a clinical trial, alginate-based mimetics significantly inhibit aneurysm recurrence due to endovascular aortic repair (EVAR).

Advantages of Us

• We introduce the desired glycosidic bonds in a high-yield and stereoselective manner to prevent the formation of indivisible (abnormal) mixtures.
• The advantage of providing synthesizer synthesis services is the ability to quickly access target structures without intermediate purification in quantities sufficient not only for biological experiments but also for the convenient verification of the structural integrity of compounds using standard ¹H and ¹³C NMR.

CD BioGlyco provides comprehensive Marine Carbohydrate development services ranging from the production and Characterization of marine polysaccharides to active development and utilization. Our high-quality service and serious project plans are recognized by our clients worldwide. We are committed to being your first choice in marine carbohydrate research. Please feel free to contact us.