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Multiple grafting to enzymatically synthesized polyesters.
Methods Enzymol 2019; 627:57-97ME

Abstract

Enzymatic polymerization is an environmentally benign process for the synthesis of biodegradable and biocompatible polymers. The regioselectivity of lipase B from Candida Antarctica (CAL-B) produces linear functional polyesters without protection-deprotection steps. In this work, two different methods for the enzymatic synthesis of functional polyesters based on renewable resources, as, e.g., glycerol, using CAL-B are outlined. Poly(glycerol adipate) was synthesized by enzymatic transesterification between glycerol and divinyl adipate or dimethyl adipate. Methods are also reported to graft poly(glycerol adipate) with different amounts of hydrophobic side chains (lauric, stearic, behenic, and oleic acids) and hydrophilic poly(ethylene glycol) side chains, respectively. The hydrophilicity or lipophilicity of grafted polyesters is well controlled by changing the degree of grafting of hydrophilic and hydrophobic side chains. The multiple grafted polyesters are characterized by NMR spectroscopy, differential scanning calorimetry, gel permeation chromatography, and X-ray diffraction. Furthermore, the self-assembly of the graft copolymers in water and their use as steric stabilizers for cubosomes are discussed. For this purpose mainly dynamic light scattering and small angle X-ray scattering have been employed.

Authors+Show Affiliations

Department of Chemistry, Martin Luther University Halle-Wittenberg, Halle (Saale), Germany.Department of Chemistry, Martin Luther University Halle-Wittenberg, Halle (Saale), Germany; Department of Pharmacy, Martin Luther University Halle-Wittenberg, Halle (Saale), Germany.Department of Pharmacy, Martin Luther University Halle-Wittenberg, Halle (Saale), Germany.Department of Pharmacy, Martin Luther University Halle-Wittenberg, Halle (Saale), Germany.Department of Pharmacy, Martin Luther University Halle-Wittenberg, Halle (Saale), Germany.Department of Chemistry, Martin Luther University Halle-Wittenberg, Halle (Saale), Germany. Electronic address: joerg.kressler@chemie.uni-halle.de.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31630748

Citation

Bilal, Muhammad Humayun, et al. "Multiple Grafting to Enzymatically Synthesized Polyesters." Methods in Enzymology, vol. 627, 2019, pp. 57-97.
Bilal MH, Alaneed R, Steiner J, et al. Multiple grafting to enzymatically synthesized polyesters. Meth Enzymol. 2019;627:57-97.
Bilal, M. H., Alaneed, R., Steiner, J., Mäder, K., Pietzsch, M., & Kressler, J. (2019). Multiple grafting to enzymatically synthesized polyesters. Methods in Enzymology, 627, pp. 57-97. doi:10.1016/bs.mie.2019.04.031.
Bilal MH, et al. Multiple Grafting to Enzymatically Synthesized Polyesters. Meth Enzymol. 2019;627:57-97. PubMed PMID: 31630748.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Multiple grafting to enzymatically synthesized polyesters. AU - Bilal,Muhammad Humayun, AU - Alaneed,Razan, AU - Steiner,Jonas, AU - Mäder,Karsten, AU - Pietzsch,Markus, AU - Kressler,Jörg, Y1 - 2019/05/29/ PY - 2019/10/22/entrez KW - CAL-B KW - Enzymatic synthesis KW - Grafted polyesters KW - Steric stabilizers SP - 57 EP - 97 JF - Methods in enzymology JO - Meth. Enzymol. VL - 627 N2 - Enzymatic polymerization is an environmentally benign process for the synthesis of biodegradable and biocompatible polymers. The regioselectivity of lipase B from Candida Antarctica (CAL-B) produces linear functional polyesters without protection-deprotection steps. In this work, two different methods for the enzymatic synthesis of functional polyesters based on renewable resources, as, e.g., glycerol, using CAL-B are outlined. Poly(glycerol adipate) was synthesized by enzymatic transesterification between glycerol and divinyl adipate or dimethyl adipate. Methods are also reported to graft poly(glycerol adipate) with different amounts of hydrophobic side chains (lauric, stearic, behenic, and oleic acids) and hydrophilic poly(ethylene glycol) side chains, respectively. The hydrophilicity or lipophilicity of grafted polyesters is well controlled by changing the degree of grafting of hydrophilic and hydrophobic side chains. The multiple grafted polyesters are characterized by NMR spectroscopy, differential scanning calorimetry, gel permeation chromatography, and X-ray diffraction. Furthermore, the self-assembly of the graft copolymers in water and their use as steric stabilizers for cubosomes are discussed. For this purpose mainly dynamic light scattering and small angle X-ray scattering have been employed. SN - 1557-7988 UR - https://www.unboundmedicine.com/medline/citation/31630748/Multiple_grafting_to_enzymatically_synthesized_polyesters L2 - https://linkinghub.elsevier.com/retrieve/pii/S0076-6879(19)30146-6 DB - PRIME DP - Unbound Medicine ER -