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Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol.
Biotechnol Lett. 2010 Oct; 32(10):1463-71.BL

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 M(W) of ~170,000 Da, whereas a M(W) 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.

Authors+Show Affiliations

Max Rubner-Institute, Federal Research Institute for Nutrition and Food, Piusallee 68/76, 48147, Münster, Germany. eberhard.fehling@mri.bund.deNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

20495948

Citation

Fehling, Eberhard, et al. "Thiol-functionalized Copolymeric Polyesters By Lipase-catalyzed Esterification and Transesterification of 1,12-dodecanedioic Acid and Its Diethyl Ester, Respectively, With 1-thioglycerol." Biotechnology Letters, vol. 32, no. 10, 2010, pp. 1463-71.
Fehling E, Bergander K, Klein E, et al. Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol. Biotechnol Lett. 2010;32(10):1463-71.
Fehling, E., Bergander, K., Klein, E., Weber, N., & Vosmann, K. (2010). Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol. Biotechnology Letters, 32(10), 1463-71. https://doi.org/10.1007/s10529-010-0311-z
Fehling E, et al. Thiol-functionalized Copolymeric Polyesters By Lipase-catalyzed Esterification and Transesterification of 1,12-dodecanedioic Acid and Its Diethyl Ester, Respectively, With 1-thioglycerol. Biotechnol Lett. 2010;32(10):1463-71. PubMed PMID: 20495948.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol. AU - Fehling,Eberhard, AU - Bergander,Klaus, AU - Klein,Erika, AU - Weber,Nikolaus, AU - Vosmann,Klaus, Y1 - 2010/05/22/ PY - 2010/03/25/received PY - 2010/05/11/accepted PY - 2010/5/25/entrez PY - 2010/5/25/pubmed PY - 2011/1/11/medline SP - 1463 EP - 71 JF - Biotechnology letters JO - Biotechnol. Lett. VL - 32 IS - 10 N2 - 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 M(W) of ~170,000 Da, whereas a M(W) 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. SN - 1573-6776 UR - https://www.unboundmedicine.com/medline/citation/20495948/Thiol_functionalized_copolymeric_polyesters_by_lipase_catalyzed_esterification_and_transesterification_of_112_dodecanedioic_acid_and_its_diethyl_ester_respectively_with_1_thioglycerol_ L2 - https://doi.org/10.1007/s10529-010-0311-z DB - PRIME DP - Unbound Medicine ER -