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Different Routes to Ampholytic Polydehydroalanine: Orthogonal versus Simultaneous Deprotection
Jan-Hendrik Kruse1,2, Philip Biehl1,2, Felix Helmut Schacher1,2
1Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstraße 10, D-07743, Jena, Germany.
Macromolecular Rapid Communications
|January 18, 2019
Summary
Researchers synthesized polydehydroalanine (PDha), a highly charged polymer, using novel monomers. The protective groups allow for controlled deprotection, enabling versatile PDha synthesis for advanced material applications.
Area of Science:
- Polymer Chemistry
- Organic Synthesis
- Materials Science
Background:
- Polydehydroalanine (PDha) is a polyampholyte with high charge density due to its repeating -NH2 and -COOH groups.
- Developing efficient synthesis routes for PDha is crucial for its application in various fields.
Purpose of the Study:
- To report the synthesis and polymerization of two novel monomers for PDha.
- To demonstrate the controlled deprotection of functional groups in the resulting polymers.
- To investigate the characteristics of the synthesized polymers.
Main Methods:
- Free radical polymerization of benzyl 2-tert-butoxycarbonylaminoacrylate and methyl 2-benzyloxycarbonylaminoacrylate.
- Polymer-analogous modification reactions to yield PDha.
- Orthogonal and simultaneous deprotection strategies for amine and carboxylic acid groups.
- Characterization using NMR spectroscopy and size exclusion chromatography.
Main Results:
- Successful synthesis and polymerization of the two protected aminoacrylate monomers.
- Formation of poly(tert-butoxycarbonylaminoacrylate) (PtBABA) and poly(benzyloxycarbonylaminoacrylate) (PBOMA).
- Demonstration of simultaneous and orthogonal deprotection to yield PDha.
- Characterization of intermediate and final polymer products.
Conclusions:
- The study presents a versatile method for synthesizing polydehydroalanine (PDha).
- The choice of protective groups allows for controlled deprotection, enabling tailored polymer properties.
- The developed polymers show potential for applications requiring high charge density materials.
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