Lipid modification of amino acids, carbohydrates and polyols

Agricultural crops provide a considerable reservoir of useful and low cost raw materials like fats and oils, plant proteins and carbohydrates. By selective combination of their molecular constituents (e. g. fatty acids, glycerol, amino acids, saccharides), a wide variety of surface active materials can be prepared. Due to their molecular constitution, all of them are potentially biodegradable. In this article we describe two generally applicable methods for the synthesis of such combination products using fatty acids from plant oils - one of the most important renewable materials as feedstock for the chemical industry - in combination with amino acids and monosaccharides including sugar alcohols. Using the high selectivities displayed by lipases, which catalyze a wide variety of transformations under very mild conditions (pH, temperature) with high atom efficiency in various non-toxic solvents and without the production of by-products or waste, numerous useful products can be obtained ranging all the way from surface active compounds (detergents and emulsifiers for food and personal care products) such as mono- and diglycerides, sugar esters, synthetic building blocks, products for food and dietary applications, all the way to novel methods for the production of biofuels (biodiesel). In our continuing effort to devise novel and generally applicable methods for the syntheses of such combination products we recently discovered a novel class of building blocks, fatty acid modified anhydrides of hydroxy carboxylic acids such as citric acid, tartaric acid and malic acid which led to alternative synthetic approaches towards new classes of the title compounds. © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.