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Modular Click Assembly DNA-Encoded Glycoconjugate Libraries with on-DNA Functional Group Transformations.
Xing Ling1,2, Sixiu Liu1,2, Yixuan Yang1
1State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 501 Haike Road, Zhang Jiang Hi-Tech Park, Pudong, Shanghai, 201203, China.
Bioconjugate Chemistry
|March 24, 2023
Summary
Researchers developed novel on-DNA methods to create DNA-encoded glycoconjugate libraries. These carbohydrate-based libraries are crucial for discovering new drug candidates targeting various pharmaceutical applications.
Area of Science:
- Carbohydrate Chemistry
- Medicinal Chemistry
- Bioconjugation
Background:
- Carbohydrates are vital natural products regulating physiological activities.
- There is a growing demand for carbohydrate-based compound libraries for drug discovery.
- Efficient methods are needed to synthesize diverse DNA-linked glycoconjugates.
Purpose of the Study:
- To develop on-DNA protocols for constructing DNA-encoded glycoconjugates.
- To enable the generation and modification of glycosyl compounds linked to DNA.
- To demonstrate the feasibility of preparing DNA-linked glycoconjugate libraries for pharmaceutical applications.
Main Methods:
- Utilized Seyferth-Gilbert homologation for on-DNA modifications.
- Employed anomeric azidation for introducing azide functionalities on-DNA.
- Applied copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) for DNA-linked glycoconjugate formation.
Main Results:
- Successfully developed a set of on-DNA protocols for glycoconjugate synthesis.
- Achieved good conversions and broad substrate scope for the on-DNA chemistries.
- Generated three distinct DNA-linked glycoconjugate libraries.
Conclusions:
- The developed on-DNA chemistries are effective for generating and modifying DNA-linked glycosyl compounds.
- The study demonstrates the applicability and feasibility of preparing DNA-encoded glycoconjugate libraries.
- These libraries can accelerate the identification of potential drug candidates for pharmaceutical targets.
