Structure-Controlled Synthesis of Polyesteramides Utilizing Sugar Diols and Amino Acids

利用糖二醇和氨基酸结构控制合成聚酯酰胺

基本信息

批准号：
16550113
负责人：
OKADA Masahiko
金额：
$ 2.3万
依托单位：
Chubu University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
2004
资助国家：
日本
起止时间：
2004 至 2006
项目状态：
已结题

项目摘要

1. Synthesis and biodegradability of polyesteramides consisting of amino acid, sugar diol, and aliphatic dicarboxylic acid unitsSome diamidodicarboxylic acids were prepared by condensations of combinations of L-phenylalanine and L-alanine with adipic acid and sebacic acid. Polyesteramides were synthesized by polycondensation of the diamidodicarboxylic acids with 1,4:3,6-dianhydro-D-glucitol (DAG) or 1,4:3,6-dianhydro-D-mannitol(DAM) in the presence of dicyclohexylcarbodiimide (DCC). NMR and IR analysis indicated that these polyesteramides were composed of well-defined structure. Enzymatic degradation and soil burial degradation tests suggested a correlation between the molecular structure and biodegradability of the polyesteramides. Those containing DAG or DAM units showed a somewhat lower degradability than that of polyesteramides containing aliphatic diol units.2. Synthesis and biodegradability of polyesteramides with hydroxyl groups as side chains.2,3-O-isopropyliden-L-threitol was prepared from L-tartaric acid via two-step reactions. The diamidodicarboxylic acid described above were polycondensed with the protected L-threitol in the presence of DCC to yield the corresponding polyesteramides. The isopropylidene protecting groups were removed by the treatment with trifluoroacetic acid to give polyesteramides having free hydroxyl groups as side chains. The introduction of hydroxyl groups significantly accelerated the biodegradation of the polyesteramides.Our research opened a promising way to synthesize structurally well-defined biodegradable polyesteramides utilizing renewable natural resources such as amino acids and sugar diols.

1。由氨基酸，糖二醇和脂肪族二羧酸单位组成的聚酯酰胺的合成和生物降解性，通过浓缩L-苯基丙氨酸和L-丙氨酸与脂肪酸和乙酸的组合来制备二氨基二羧酸。通过在二氯克洛克洛己基己糖甲基二维（DCC）的情况下，通过与1,4：3,6-二羟基二糖醇（DAG）或1,4：3,6-二羟基氢丙醇（DAG）或1,4：3,6-二羟基甲硝基（DAG）合成聚二酰胺，或1,4：3,6-二羟基氢-D-葡萄醇（DAG）或1,4：3,6-二羟基氢-D-甘露醇（DAM）。 NMR和IR分析表明，这些聚酯酰胺由定义明确的结构组成。酶促降解和土壤埋葬降解检验表明，分子结构与聚酯酰胺的生物降解性之间存在相关性。与含有脂肪族二醇单位的聚二酰胺相比，包含DAG或大坝单元的降解性较低。2。聚酯酰胺与羟基作为侧链的合成和生物降解性。2,3-O-异丙基丙烯 - L-硫二醇通过两步反应从L-tartaric酸制备。在DCC存在下，将上述的二氨基二羧酸与受保护的L-硫醇的多限，以产生相应的聚酯酰胺。通过用三氟乙酸处理去除异丙基丙烯组，使聚羟基作为侧链的聚二酰胺。羟基的引入显着加速了聚酯酰胺的生物降解。我们的研究开辟了一种有前途的方法，利用氨基酸和糖二醇等可再生自然资源来合成结构定义明确的可生物降解的聚酯酰胺。