Abstract
A facile and flexible chemoenzymatic route for the preparation of a variety of amino acid-based surfactants ranging from simple monoesters to more complex bola- and gemini-amphiphiles is described. The methodology is based on the observation that some lipases, notably immobilized Candida antarctica and Rhizomucor miehei, readily accept N-Cbzamino acids as substrates and catalyze their esterification/amidation with long-chain alcohols and α,ω-diols/α,ω-diamines in excellent yield. The resulting alkanediyl-α,ω-bis-(N-Cbz-amino acid) can be either deprotected using conventional procedures to attain a number of multifunctional bola-amphiphiles or further modified to obtain a range of amino acid-based gemini surfactants.
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Valivety, R., Gill, I.S. & Vulfson, E.N. Application of enzymes to the synthesis of amino acid-based bola and gemini surfactants. J Surfact Deterg 1, 177–185 (1998). https://doi.org/10.1007/s11743-998-0017-3
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DOI: https://doi.org/10.1007/s11743-998-0017-3