Two-Step Enzymatic Synthesis of Biocompatible Polymers Made from Cholic Acid

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• 作者：Élyse Champagne ; Nicolas Lévaray ; X. X. Zhu
• 刊名：ACS Sustainable Chemistry & Engineering
• 出版年：2017
• 出版时间：January 3, 2017
• 年：2017
• 卷：5
• 期：1
• 页码：689-695
• 全文大小：397K
• ISSN：2168-0485

文摘

Polyesters are known biodegradable materials that are frequently used for biomedical applications that require biocompatibility. Their synthesis usually requires transition metal catalysts, which may become a source of contamination. In addition, using such compounds translates to extensive purification procedures, which do not agree with green chemistry principles. In addition to being renewable, enzymes such as lipases are milder for biological systems, and were studied for both ring-closure and ring-opening reactions. Here, Candida antarctica lipase B was used in ring-closure, reducing a two-step synthesis to a single step with 58% yield. The bile acid-containing macrocycles were subsequently polymerized with the same enzyme; relatively high molar masses (40 000 g/mol) were obtained. The conditions for the enzymatic ring-closure and ring-opening reactions were established through the reaction of thapsic acid with 1,10-decanediol. The di- and tetralactones afforded semicrystalline polymers with relatively high molar masses. Therefore, lipases were successfully used for both ring-closing reactions and ring-opening polymerizations of large rigid moieties as well as more flexible structures. The use of enzymes for the multistep syntheses shows their utility as a simple and green method for monomer and polymer synthesis with better biocompatibility and tunable properties.