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Unnatural cyclodextrins can be accessed from enzyme-mediated dynamic combinatorial libraries.
Dennis Larsen1, Michel Ferreira2, Sébastien Tilloy2
1Department of Chemistry, Technical University of Denmark, Kongens Lyngby DK-2800, Denmark. denl@kemi.dtu.dk.
Chemical Communications (Cambridge, England)
|January 26, 2022
Summary
Enzyme-mediated dynamic combinatorial chemistry using cyclodextrins (CDs) can incorporate unnatural building blocks. This method allows for controlled synthesis of modified CDs by template addition, expanding chemical diversity.
Area of Science:
- Biotechnology
- Organic Chemistry
- Enzymology
Background:
- Enzyme-mediated dynamic combinatorial chemistry (EDCC) offers a powerful route to complex molecules.
- Cyclodextrins (CDs) are versatile cyclic oligosaccharides with broad applications.
- Expanding EDCC to incorporate unnatural building blocks is crucial for novel molecular discovery.
Purpose of the Study:
- To investigate the incorporation of unnatural glucopyranose-derived building blocks into dynamic cyclodextrin systems.
- To explore the use of cyclodextrin glucanotransferase (CGTase) for synthesizing modified CDs.
- To develop a template-controlled method for accessing specific modified cyclodextrin populations.
Main Methods:
- Utilizing native cyclodextrin glucanotransferase (CGTase) to catalyze reactions.
- Employing synthetically modified glucopyranose substrates within dynamic combinatorial libraries.
- Applying template molecules to control the relative concentrations of different modified CDs.
Main Results:
- Demonstrated successful incorporation of unnatural glucopyranose-derived building blocks into CDs.
- Showcased the generation of dynamic mixtures containing various modified cyclodextrins (α, β, γ).
- Established template-dependent control over the relative abundance of specific modified CDs.
Conclusions:
- Unnatural building blocks can be integrated into CD systems via CGTase-mediated EDCC.
- This approach significantly broadens the scope of EDCC by enabling the use of modified substrates.
- Template-controlled synthesis provides a novel strategy for accessing tailored libraries of modified cyclodextrins.
