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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. [ABSTRACT FROM AUTHOR]