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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、糖二醇和脂肪族二元羧酸单元组成的聚酯酰胺的合成及其生物降解性通过L-苯丙氨酸和L-丙氨酸与己二酸和癸二酸的组合物的缩合反应制备了一些二酰胺基二元酸。在二环己基碳二亚胺（DCC）存在下，二酰胺基二羧酸与1，4：3，6-二脱水-D-葡萄糖醇（DAG）或1，4：3，6-二脱水-D-甘露醇（DAM）进行缩聚反应，合成了聚酯酰胺。NMR和IR分析表明，这些聚酯酰胺具有明确的结构。酶降解和土壤埋藏降解试验表明，聚酯酰胺的分子结构和生物降解性之间的相关性。含DAG或DAM单元的聚酯酰胺的降解性略低于含脂肪族二醇单元的聚酯酰胺。以L-酒石酸为原料，经两步反应合成了2，3-O-亚异丙基-L-苏糖醇。将上述二酰氨基二羧酸与保护的L-苏糖醇在DCC存在下缩聚，得到相应的聚酯酰胺。通过用三氟乙酸处理除去异亚丙基保护基团，得到具有游离羟基作为侧链的聚酯酰胺。羟基的引入显著地加速了聚酯酰胺的生物降解，我们的研究为利用可再生的天然资源如氨基酸和糖二醇合成结构明确的可生物降解聚酯酰胺开辟了一条很有前途的途径。