Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol

• Published in: Biotechnology Letters
• Language: English
• Published: Springer Netherlands 2011
• Subjects: Esterification; 1,12-Dodecanedioic acid; Immobilized lipase B from Candida antarctica; Poly(diethyl 1,12-dodecanedioate-co-1-thioglycerol); Poly(1,12-dodecanedioic acid-co-1-thioglycerol); 1-Thioglycerol (3-mercaptopropane-1,2-diol); Klaus; Antarc*; Antarctica
• Online Access: http://hdl.handle.net/2262/55955; https://doi.org/10.1007/s10529-010-0311-z

Abstract Copolymeric polyoxoesters containing branched-chain methylenethiol functions, i.e., poly(1,12-dodecanedioic acid-co-1-thioglycerol) and poly(diethyl 1,12-dodecanedioate-co-1-thioglycerol), were formed by lipase-catalyzed polyesterification and polytransesterification of 1,12-dodecanedioic acid and diethyl 1,12-dodecanedioate, respectively, with 1-thioglycerol (3-mercaptopropane-1,2-diol) using immobilized lipase B from Candida antarctica (Novozym 435) in vacuo without drying agent in the reaction mixture. After 360?480 h, both polyoxoesters were purified by extraction from the reaction mixtures followed by solvent fractionation. The precipitate of poly(1,12-dodecanedioic acid-co-1-thioglycerol) demonstrated a MW of ~170,000 Da, whereas a MW of ~7,100 Da only was found for poly(diethyl 1,12-dodecanedioate-co-1-thioglycerol). Both polycondensates were analyzed by GPC/SEC, alkali-catalyzed transmethylation, NMR- and FTIR-spectrometry. phone: [phone] (Fehling, Eberhard) [e-mail] (Fehling, Eberhard) Max Rubner-Institute, Federal Research Institute for Nutrition and Food - Piusallee 68/76 - 48147 - Munster - GERMANY (Fehling, Eberhard) Institute for Organic Chemistry, University of Munster - 48149 - Munster - GERMANY (Bergander, Klaus) Max Rubner-Institute, Federal Research Institute for Nutrition and Food - Piusallee 68/76 - 48147 - Munster - GERMANY (Klein, Erika) Max Rubner-Institute, Federal Research Institute for Nutrition and Food - Piusallee 68/76 - 48147 - Munster - GERMANY (Weber, Nikolaus) Max Rubner-Institute, Federal Research Institute for Nutrition and Food - Piusallee 68/76 - 48147 - Munster - GERMANY (Vosmann, Klaus) GERMANY Registration: 2010-05-12 Received: 2010-03-25 Accepted: 2010-05-11 ePublished: 2010-05-22