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Two-step biocatalytic route to biobased functional polyesters from omega-carboxy fatty acids and diols.
Biomacromolecules. 2010 Jan 11; 11(1):259-68.B

Abstract

Biobased omega-carboxy fatty acid monomers 1,18-cis-9-octadecenedioic, 1,22-cis-9-docosenedioic, and 1,18-cis-9,10-epoxy-octadecanedioic acids were synthesized in high conversion yields from oleic, erucic and epoxy stearic acids by whole-cell biotransformations catalyzed by C. tropicalis ATCC20962. Maximum volumetric yields in shake-flasks were 17.3, 14.2, and 19.1 g/L after 48 h conversion for oleic acid and 72 h conversions for erucic and epoxy stearic acids, respectively. Studies in fermentor with better control of pH and glucose feeding revealed that conversion of oleic acid to 1,18-cis-9-octadecenedioic acid by C. tropicalis ATCC20962 occurred with productivities up to 0.5 g/L/h. The conversion of omega-carboxy fatty acid monomers to polyesters was then studied using immobilized Candida antarctica Lipase B (N435) as catalyst. Polycondensations with diols were performed in bulk as well as in diphenyl ether. The retension of functionality from fatty acid, to omega-carboxy fatty acid monomer and to corresponding polyesters resulted in polymers with with unsaturated and epoxidized repeat units and M(w) values ranging from 25000 to 57000 g/mol. These functional groups along chains disrupted crystallization giving materials that are low melting (23-40 degrees C). In contrast, saturated polyesters prepared from 1,18-octadecanedioic acid and 1,8-octanediol have correspondingly higher melting transitions (88 degrees C). TGA results indicated that all synthesized polyesters showed high thermal stabilities. Thus, the preparation of functional monomers from C. tropicalis omega-oxidation of fatty acids provides a wide range of new monomer building blocks to construct functional polymers.

Authors+Show Affiliations

NSF I/UCRC for Biocatalysis and Bioprocessing of Macromolecules, Department of Chemical and Biological Sciences, Polytechnic Institute of NYU, Six Metrotech Center, Brooklyn, New York 11201, USA.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

20000460

Citation

Yang, Yixin, et al. "Two-step Biocatalytic Route to Biobased Functional Polyesters From Omega-carboxy Fatty Acids and Diols." Biomacromolecules, vol. 11, no. 1, 2010, pp. 259-68.
Yang Y, Lu W, Zhang X, et al. Two-step biocatalytic route to biobased functional polyesters from omega-carboxy fatty acids and diols. Biomacromolecules. 2010;11(1):259-68.
Yang, Y., Lu, W., Zhang, X., Xie, W., Cai, M., & Gross, R. A. (2010). Two-step biocatalytic route to biobased functional polyesters from omega-carboxy fatty acids and diols. Biomacromolecules, 11(1), 259-68. https://doi.org/10.1021/bm901112m
Yang Y, et al. Two-step Biocatalytic Route to Biobased Functional Polyesters From Omega-carboxy Fatty Acids and Diols. Biomacromolecules. 2010 Jan 11;11(1):259-68. PubMed PMID: 20000460.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Two-step biocatalytic route to biobased functional polyesters from omega-carboxy fatty acids and diols. AU - Yang,Yixin, AU - Lu,Wenhua, AU - Zhang,Xiaoyan, AU - Xie,Wenchun, AU - Cai,Minmin, AU - Gross,Richard A, PY - 2009/12/17/entrez PY - 2009/12/17/pubmed PY - 2010/2/27/medline SP - 259 EP - 68 JF - Biomacromolecules JO - Biomacromolecules VL - 11 IS - 1 N2 - Biobased omega-carboxy fatty acid monomers 1,18-cis-9-octadecenedioic, 1,22-cis-9-docosenedioic, and 1,18-cis-9,10-epoxy-octadecanedioic acids were synthesized in high conversion yields from oleic, erucic and epoxy stearic acids by whole-cell biotransformations catalyzed by C. tropicalis ATCC20962. Maximum volumetric yields in shake-flasks were 17.3, 14.2, and 19.1 g/L after 48 h conversion for oleic acid and 72 h conversions for erucic and epoxy stearic acids, respectively. Studies in fermentor with better control of pH and glucose feeding revealed that conversion of oleic acid to 1,18-cis-9-octadecenedioic acid by C. tropicalis ATCC20962 occurred with productivities up to 0.5 g/L/h. The conversion of omega-carboxy fatty acid monomers to polyesters was then studied using immobilized Candida antarctica Lipase B (N435) as catalyst. Polycondensations with diols were performed in bulk as well as in diphenyl ether. The retension of functionality from fatty acid, to omega-carboxy fatty acid monomer and to corresponding polyesters resulted in polymers with with unsaturated and epoxidized repeat units and M(w) values ranging from 25000 to 57000 g/mol. These functional groups along chains disrupted crystallization giving materials that are low melting (23-40 degrees C). In contrast, saturated polyesters prepared from 1,18-octadecanedioic acid and 1,8-octanediol have correspondingly higher melting transitions (88 degrees C). TGA results indicated that all synthesized polyesters showed high thermal stabilities. Thus, the preparation of functional monomers from C. tropicalis omega-oxidation of fatty acids provides a wide range of new monomer building blocks to construct functional polymers. SN - 1526-4602 UR - https://www.unboundmedicine.com/medline/citation/20000460/Two_step_biocatalytic_route_to_biobased_functional_polyesters_from_omega_carboxy_fatty_acids_and_diols_ L2 - https://dx.doi.org/10.1021/bm901112m DB - PRIME DP - Unbound Medicine ER -