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Merging Solid-Phase Peptide Synthesis and Automated Glycan Assembly to Prepare Lipid-Peptide-Glycan Chimeras
Manuel G Ricardo1, Peter H Seeberger1,2
1Department of Biomolecular Systems, Max-Planck-Institute of Colloids and Interfaces, Am Muehlenberg 1, 14476, Potsdam, Germany.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|June 26, 2023
Summary
Researchers developed a new method to create peptide-glycan chimeras, combining solid-phase peptide and glycan synthesis. This innovation enables the creation of novel glycan-based nanomaterials with enhanced biological properties.
Area of Science:
- Biomaterials Science
- Organic Chemistry
- Nanotechnology
Background:
- Conjugating glycans to nanostructured peptides enhances biomaterial biological features.
- Creating peptide-glycan chimeras demands high chemoselectivity.
Purpose of the Study:
- To expedite the synthesis of peptide-glycan chimeras.
- To explore the on-resin generation of glycan-linked molecules.
- To develop novel glycan-based nanomaterials.
Main Methods:
- Merging peptide and glycan solid-phase syntheses using a bifunctional monosaccharide.
- On-resin generation of α(1→6)tetramannoside and β(1→6)tetraglucoside linked to various molecules.
- Automated synthesis of self-assembling peptide chimeras.
Main Results:
- A robust synthetic protocol yielding approximately 20% overall was established.
- The β(1→6)tetraglucoside FFKLVFF chimera formed micelles, unlike peptide-only nanofibers.
- Peptide amphiphile-glycan chimeras formed a disperse fiber network.
Conclusions:
- The developed method provides efficient access to peptide-glycan chimeras.
- The resulting chimeras exhibit altered self-assembly properties compared to parent peptides.
- This work opens avenues for designing new glycan-based nanomaterials.
