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. 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 evaluation of their antibacterial activity.

Synthesis of O-acylated amino acid surfactants with hydrophobic ω-alkenyl chains

253rd National Meeting (2017)

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