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Genetic Incorporation of Biosynthesized L-dihydroxyphenylalanine (DOPA) and Its Application to Protein Conjugation
Published on: August 24, 2018
Synthesis and crosslinking of L-DOPA containing polypeptide vesicles
Eric P Holowka1, Timothy J Deming
1Department of Bioengineering, University of California, Los Angeles, 5121 Engineering 5, Los Angeles, CA 90095, USA.
Macromolecular Bioscience
|February 6, 2010
Summary
We synthesized DOPA-containing copolypeptides that self-assemble into vesicles. Oxidative crosslinking, mimicking mussel adhesive proteins, significantly enhanced vesicle stability in various conditions.
Area of Science:
- Biomaterials Science
- Polymer Chemistry
- Biochemistry
Background:
- Mussel adhesive proteins utilize DOPA residues for robust underwater adhesion through oxidative crosslinking.
- Self-assembly of polypeptides offers a route to create complex nanostructures like vesicles.
- Controlling vesicle stability is crucial for their application in various fields.
Purpose of the Study:
- To synthesize DOPA-containing diblock copolypeptides and investigate their self-assembly into spherical vesicles.
- To evaluate the effect of DOPA content on vesicle formation and properties.
- To assess the enhanced stability of DOPA-crosslinked vesicles compared to non-crosslinked counterparts.
Main Methods:
- Synthesis of diblock copolypeptides with varying DOPA content in hydrophobic segments.
- Self-assembly of copolypeptides into spherical vesicles in aqueous solution.
- Oxidative crosslinking of DOPA residues using an oxidizing agent in water.
- Assessment of vesicle stability under challenging conditions: freeze-drying, organic solvents, osmotic stress, and complex media.
Main Results:
- Spherical vesicles were successfully formed from copolypeptides with DOPA content up to 100%.
- Oxidative crosslinking of DOPA residues in water led to significantly improved vesicle membrane stability.
- Crosslinked vesicles demonstrated enhanced resistance to degradation by freeze-drying, organic solvents, osmotic stress, and complex media compared to non-crosslinked vesicles.
- Biomimetic crosslinker DOPA can be directly incorporated into the polypeptide sequence during synthesis.
Conclusions:
- DOPA-containing diblock copolypeptides can self-assemble into stable, crosslinkable vesicles.
- Biomimetic oxidative crosslinking of DOPA residues provides a powerful strategy to enhance vesicle stability.
- These DOPA-crosslinked vesicles offer a promising platform for various applications requiring robust biomaterials.
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