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JoVE Journal
Chemistry
Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides
Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides
JoVE Journal
Chemistry
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JoVE Journal Chemistry
Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides

Synthesis and Characterization of 1,2-Dithiolane Modified Self-Assembling Peptides

Full Text
7,757 Views
09:54 min
August 20, 2018

DOI: 10.3791/58135-v

Ruben Neves1, Kailyn Stephens1, Jillian E. Smith-Carpenter1

1Department of Chemistry and Biochemistry,Fairfield University

A protocol for the synthesis of a 1,2-dithiolane modified peptide and the characterization of the supramolecular structures resulting from the peptide self-assembly.

As structures to increase the functionality of supermolecular structures grows, this method of incorporating 1, 2-dithiolane groups with self-assembling peptides can help answer key questions about reactivity on supermolecular surfaces. The main advantage of this technique is that the coupling and deprotection of the 1, 2-dithiolane precursor molecule occurs on resin with only a single purification step of the final modified peptide. As the time it takes the assemblies to mature into their final supermolecular structures varies, visual demonstration of the characterization methods and results for the supermolecular assemblies is critical.

To synthesize the dithiolane precursor, first dissolve one gram of 3-bromo-2-proprionic acid in approximately four milliliters of one-molar sodium hydroxide in a 50-milliliter round-bottomed reaction flask at 55 degrees Celsius with stirring. When all of the reagent has been suspended in solution, seal the reaction flask with a septa and place the flask under nitrogen atmosphere. Next, add 1.49 grams of potassium thioacetate and three milliliters of two-molar sulfuric acid to four milliliters of deionized water to create thioacetic acid in situ.

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