Effect of fatty acid chain length on initial reaction rates and regioselectivity of lipase-catalysed esterification of disaccharides

• Published in: Carbohydrate research 2002-07, Vol.337 (13), p.1179-1184
• Main Authors: Pedersen, Ninfa R, Wimmer, Reinhard, Emmersen, Jeppe, Degn, Peter, Pedersen, Lars H
• Format: Article
• Language: English
• Subjects: Candida - enzymology; Catalysis; Disaccharides; Disaccharides - chemistry; Enzymes, Immobilized - metabolism; Esterification; Fatty acids; Fatty Acids - chemistry; Fungal Proteins; Kinetics; Lipase; Lipase - metabolism; Molecular Conformation; Solubility; Solvents; Substrate Specificity
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(02)00112-X

In a reaction medium mixture of 9:11 t-BuOH and pyridine (v/v) the effect of fatty acid chain length (C-4–C-12) on C. antarctica lipase B (Novozym 435, EC 3.1.1.3) catalysed esterification was studied. α and β maltose 6′- O-acyl esters in an anomeric molar ratio of 1.0:1.1 were synthesised independently of the chain length, but the initial specific reaction rate increased with decreasing chain length of the acyl donor. The product yield followed the same trend with a lauryl ester yield of 1.1% (mol/mol) and a butyl ester yield of 27.6% (mol/mol) after 24 h of reaction. With sucrose as the acyl acceptor the 6′- O-acyl and 6- O-acyl monoesters were formed with fatty acids of chain length C-4 and C-10 while the 6′,6- O-acyl diester was formed only with butanoic acid (C-4:0) as acyl donor. The 6′- O-acyl and 6- O-acyl monoesters and the 6′,6- O-acyl diester of butanoic acid were produced in a molar ratio of 1.0:0.5:0.2 and with decanoic acid (C-10:0) the 6′- O-acyl and 6- O-acyl monoesters were formed in the ratio of 1.0:0.3. The highest initial reaction rate and yield were obtained with the shortest chain length of the acyl donor. Initial reaction rates and ester yields were affected by the solubility of the disaccharide, with higher reaction rates and yields with maltose than with sucrose, while no formation of esters were observed with either cellobiose or lactose as acyl acceptors. Fatty acid esters of sucrose and maltose were synthesised in a lipase-catalysed esterification process. R=(CH 2) n CH 3 n=3 and 9.