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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
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Summary
This summary is machine-generated.

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.

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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.