Lipase-catalyzed synthesis of quinate and glucuronate fatty esters

Abstract

Lipase-catalyzed synthesis of quinate and glucuronate fatty estersThe lipase-catalyzed synthesis of fatty alcohol esters of quinic and glucuronic acid was investigated. The results showed that although a direct esterification process was possible, a strategy involving short-chain alkyl ester intermediates was advantageous. 2-Methyl-2-butanol was chosen as solvent and parameters such as substrate ratios and concentrations were optimized. Octyl, decyl and hexadecyl esters of quinic and glucuronic acids could be obtained with this process. However, reaction rates were rather slow and it could be shown that the completely chemically catalyzed synthesis of the same products using ion exchange resins was advantageous.

The use of lipases as biocatalysts for the epoxidation of fatty acids and phenolic compounds

“…25 Unfortunately, very hydrophobic solvents are not always adapted for lipase-catalyzed reactions involving polar substrates such as sugars, amino acids or phenolic compounds, 15 these molecules being poorly soluble in these solvents. Therefore, solvents with intermediate polarities are often used and examples have been given on the use of acetonitrile, 26,27 tert-butanol, 28 2-methyl-2-butanol [29][30][31] or acetone. 32 However, due to the difficulties in selecting an appropriate solvent that has to preserve lipase activity, allow good solubility of all the substrates and exhibit limited toxicity, some alternatives have been studied recently.…”