Synthesis and Characterization of Glyco-SAMs on Gold Nanoparticles: A Modular Approach Towards Glycan-Based...

Area of Science:

• Biochemistry
• Materials Science
• Nanotechnology

Background:

• Significant interest exists in tools for investigating carbohydrate-protein interactions (CPI) and carbohydrate-carbohydrate interactions (CCI).
• Existing techniques for analyzing CPI/CCI have limitations in synthesis and control.
• Mimicking the glycocalyx requires self-assembled monolayer (SAM) formation of carbohydrate derivatives on gold nanoparticles.

Purpose of the Study:

• To develop a novel, facile, and rapid method for synthesizing and immobilizing carbohydrate derivatives on gold nanoparticles.
• To enhance binding events by controlling ligand amount and orientation for studying CPI and CCI.
• To present effective immobilization and initial binding studies for biomimetic applications and diagnostics.

Main Methods:

• Synthesis of diverse aldehyde-functionalized glycan structures (mono-, di-, and trisaccharides) using methods including olefin metathesis.
• Immobilization of synthesized glycans onto biorepulsive aminooxy-functionalized gold nanoparticles via oxime coupling.
• Characterization of immobilization and initial binding studies using the lectin concanavalin A.

Main Results:

• A novel approach for facile and rapid synthesis of linked spacers and carbohydrate derivatives was achieved.
• Controlled amount and orientation of ligands were achieved, enhancing binding events.
• Effective immobilization of glycans and successful initial binding studies with concanavalin A were demonstrated.

Conclusions:

• The developed immobilization method is advantageous for studying carbohydrate interactions.
• This technique facilitates biomimetic studies of carbohydrates.
• The method is applicable for carbohydrate-based array development in diagnostics and screening.