Organic Synthesis of L-Leucine and L-phenylalanine O-acylated Amino Acid Surfactants to Examine Antibacterial Properties — Presentation Detail — Celebration of Scholars

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Additional Information

More information is available at carthage.edu/celebration-scholars/. The following are members of the Research, Scholarship, and Creativity Committee who are eager to listen to ideas and answer questions:

Jun Wang
Kim Instenes
John Kirk
Nora Nickels
Andrew Pustina
James Ripley

Organic Synthesis of L-Leucine and L-phenylalanine O-acylated Amino Acid Surfactants to Examine Antibacterial Properties

Name: Aileen Szczepanski
Major: Biology
Hometown: Kenosha
Faculty Sponsor: David Brownholland
Other Sponsors:
Type of research: SURE

Abstract

Surfactants are surface-active materials with numerous applications, including: detergents and soaps, cosmetics, fabric softeners, pharmaceutical creams and ointments, and plasticizers. Amino acid-surfactants have generated interest as antibacterial agents, chiral resolution, chelating agents, and as switchable surfactants. These surfactants are of particular interest because they are largely biodegradable, due to a relatively labile ester or amide bond. We describe the synthesis of O-acylated amino acid surfactants with hydrophobic ω-alkenyl chains. Initially, N-Boc amino acids were acylated with ω-undecylenyl alcohol using a Fischer esterification reaction followed by deprotection of the Boc protecting group with trifluoroacetic acid. Future work will include characterization of micelles generated from these novel amino acids, as well as evaluation of their antibacterial activity.