Application of enzymes to the synthesis of amino acid‐based bola and gemini surfactants

Abstract

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.