Overview of Coupling Reaction-based DEGL

The coupling reaction is a chemical strategy and method for covalently linking two molecules and has been used in various biotechnological applications, such as DNA-encoded Glycan Libraries. Coupling reaction has several significant advantages in the synthesis of DNA-encoded libraries (DEL). Firstly, their high efficiency and selectivity allow for the accurate joining of specific molecules even in complex systems, ensuring high accuracy and reproducibility of the resulting glycosyl-DEL. Second, the coupling reaction is usually carried out under mild conditions, which avoids the destruction of the glycosyl structure under extreme conditions and ensures the integrity of the glycan chain. In addition, the diversity of coupling reaction types, including amidation, acylation, etherification, etc., provides a flexible means of glycosyl modification to meet a variety of research needs.

Fig.1 A few common coupling reactions. (CD BioGlyco)

Based on these multiple advantages, CD BioGlyco develops and designs coupling reactions for the rapid and precise attachment of a wide range of glycan molecules to DNA coding fragments to create DEGLs with diversity. Through our coupling reaction-based DEGL customized construction, clients obtain a library of glycans with a high degree of structural diversity and a precise DNA-encoded glycan library.

Empowering Discovery: Harnessing Coupling Reactions for Advanced DEGLs

Our dedicated team of professionals is committed to driving this technology forward to meet the needs of DEGL construction in different fields. We ensure that each DEGL meets industry-leading quality standards by continuously optimizing reaction conditions and improving synthesis efficiency.

Preparation of DNA Tags

We prepare a specific DNA tag for each particular glycan, which generally contains a sequence to encode the particular glycan. In this process, we design DNA tags that incorporate the diversity and binding properties of the glycan.

Preparation of Glycan-DNA Couplings Using Coupling Reactions

Due to the diversity of coupling reactions and the fact that most of them fulfill the conditions for DNA compatibility, we use coupling reactions to assemble glycans and DNA. This step is the core step in constructing DEGL. For this reason, we provide our clients with a variety of coupling options to ensure that the results obtained meet their research needs.

• Lightcatalytic Coupling
  • Common light-catalysts are ruthenium- or rhodium-based compounds that produce active intermediates under visible light irradiation. We dissolve and mix the glycan building block with DNA starting material and add an appropriate amount of light catalysts. The solution is irradiated by a light source (e.g. a blue LED lamp), and the catalyst is activated by the light, which promotes the reaction and yields the on-DNA glycan coupling product.
• C-H Activation
  • The C-H activation reaction can be carried out by adding a catalyst to a mixture of a glycan and a DNA fragment under suitable temperature and reaction conditions.
  • For example, by placing a glycan containing a benzene ring and a DNA fragment with a phosphate group in an oxygenated solvent or an ionic liquid, the benzene ring structure and the phosphate group can be coupled by C-H activation to obtain a glycan-DNA coupling. In this process, we selectively use palladium-, iridium- or rhodium-based catalysts and suitable conditions to activate the C-H bonds.
• Olefin Addition
  • Olefin addition can be used to efficiently couple glycans and DNA fragments. The glycan or DNA fragment used for the synthesis of glycan-DNA couplings by this method needs to contain an olefinic structure, such as an allyl or alkynyl group. Also, we start the reaction under proper heat or light conditions.

Construction of DEGL

After selecting the appropriate conditions for library construction, we use enzymatic catalysis to attach the DNA tag to the starting material, followed by on-DNA chemical reactions. After the reaction is complete, the synthesized compound library is purified and re-dissolved, evenly divided, and the same operation is repeated for the selected on-DNA conjugation reaction. Finally, we "pool" all the reaction products, and purify and characterize them, completing the construction of the coupling reaction-based DEGL.

Our DEGLs are suitable for screening a wide range of target proteins or receptors, such as enzymes, antibodies, and living cell surface receptors. We also design DEGL solutions according to the client's needs and construct DEGLs in the millions, tens of millions, and even hundreds of millions.

Workflow

In our coupling reaction-based DEGL construction service, we incorporate advanced coupling reaction technologies to achieve efficient and reliable glycan molecule synthesis and screening. Below is the specific workflow diagram of our service, which shows a series of steps from library construction to screening molecules, ensuring efficiency and precision at every step.

Applications

• Coupling reaction-based DEGL can be used to screen and identify glycan molecules that bind specifically to target proteins or cell surface receptors, contributing to the discovery of new drug candidates.
• Coupling reaction-based DEGL can be used to identify glycan structures capable of inducing an immune response, thereby accelerating the development of vaccines.
• Using high-throughput screening with coupling reaction-based DEGL, researchers can discover glycan molecules associated with specific disease states for use in early prognostic evaluation of disease research.

Advantages

• Our team of chemists specializes in the use of diverse coupling reactions, including click chemistry, amide bond formation, and more, to ensure the efficient synthesis and diversity of DEGL.
• Our DEGL research team has mastered advanced DNA coding techniques to ensure accurate labeling and identification of each glycan molecule.
• We provide personalized coupling reaction-based DEGL design and construction solutions according to the client's needs, as well as providing continuous optimization of coupling reaction-based DEGL.

Publication Data

Frequently Asked Questions

• What is a coupling reaction and what specific types are included?
  • A coupling reaction is an organic chemical reaction in which two chemical entities (or units) combine to form a single molecule. Depending on the type, coupling reactions can be classified as:
  • Cross-coupling reactions: Two different fragments join to form one molecule.
  • Self-coupling reactions: Two identical fragments form a molecule.
• Where are coupling reactions specifically used in DEGL construction?
  • In DEGL construction, coupling reactions are used in two main ways: initial coupling and coupling in library expansion. That is the coupling of different glycan molecules to specific DNA tags, as well as further coupling steps during multistep synthesis or library expansion that can incorporate more diversity or modify existing molecular structures.

CD BioGlyco has a wide range of expertise in the construction of coupling reaction-based DEGLs and a team of specialists dedicated to providing the highest quality of service to each of our clients. We provide custom coupling reaction-based DEGL solutions for a wide range of research needs, ensuring that our products are optimized for use in glycobiology and beyond. Please feel free to contact us if you have any questions about our technology or would like to discuss further collaboration possibilities.

• DNA-encoded Single-Pharmacophore Glycan Library
• DNA-encoded Dual-Pharmacophore Glycan Library
• DNA-encoded Trio-Pharmacophore Glycan Library
• Solid Phase-based DNA-encoded Glycan Library (DEGL)
• Liquid Phase-based DNA-encoded Glycan Library (DEGL)
• DNA-encoded Natural Glycan Library
• DNA-encoded Modified Glycan Library
• DNA-encoded Glycan Antigen Library
• DNA-encoded Glycopeptide Library
• Monovalent DNA-encoded Glycan Library (DEGL)
• Multivalent DNA-encoded Glycan Library (DEGL)
• Scaffold-based DNA-encoded Glycan Library (DEGL)
• Target-based DNA-encoded Glycan Library (DEGL)
• DNA-encoded Glycan Macrocycle Library
• DNA-encoded Glycan Covalent Inhibitor Library
• DNA-encoded Glycoprotein Degrader Library
• DNA-encoded Glycan Allosteric Inhibitor Library
• Light Crosslinking DNA-encoded Glycan Library (DEGL)
• DNA-encoded Dynamic library (DEDL)
• Multi-component Reaction-based DNA-encoded Glycan Library (DEGL)
• Photocatalytic Cycloaddition-based DNA-encoded Glycan Library (DEGL)
• Aromatic Heterocyclization-based DNA-encoded Glycan Library (DEGL)
• Non-aromatic Heterocyclization-based DNA-encoded Glycan Library (DEGL)
• Carbocyclization-based DNA-encoded Glycan Library (DEGL)
• Macrocyclization-based DNA-encoded Glycan Library (DEGL)
• Click Chemistry-based DNA-encoded Glycan Library (DEGL)