Premium
Application of enzymes to the synthesis of amino acid‐based bola and gemini surfactants
Author(s) -
Valivety Rao,
Gill Iqbal S.,
Vulfson Evgeny N.
Publication year - 1998
Publication title -
journal of surfactants and detergents
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.349
H-Index - 48
eISSN - 1558-9293
pISSN - 1097-3958
DOI - 10.1007/s11743-998-0017-3
Subject(s) - chemistry , yield (engineering) , rhizomucor miehei , amino acid , amphiphile , organic chemistry , candida antarctica , enzyme , micelle , lipase , combinatorial chemistry , triacylglycerol lipase , biochemistry , polymer , aqueous solution , materials science , copolymer , metallurgy
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.