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首页> 外文期刊>Chemistry: A European journal >Combinatorial library of low molecular-weight organo-and hydrogelators based on glycosylated amino acid derivatives by solid-phase synthesis
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Combinatorial library of low molecular-weight organo-and hydrogelators based on glycosylated amino acid derivatives by solid-phase synthesis

机译：固相合成基于糖基化氨基酸衍生物的低分子量有机和水凝胶化剂的组合文库

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摘要

A combinatorial approach for the synthesis of supramolecular gelators as new organic materials is described herein. In the course of the development of a convenient and flexible solid-phase synthesis of the artificial glycolipids, some of these compounds were accidentally found to act as low molecular-weight gelators toward organic solvents. Using this combinatorial solid-phase synthesis of glycosylated amino acetates, screening and optimization of low molecular-weight organo/hydro-gelators were efficiently carried out. We found that an N-acetyl-galactosamine-appended amino acid ester (GalNAc-aa) efficiently gelates a broad spectrum of organic solvents. More interestingly, some GalNAc-aa derivatives displayed an excellent hydrogelation capability. Transmission electron microscopy, scanning electron microscopy, confocal laser scanning microscopy, and FT-IR were used for characterization of the gel structure. It is indicated that supramolecular fibers supported by strong hydrogen-bonding networks are entangled so that the resulting spaces can immobilize a number of solvent molecules effectively. In addition, the supramolecular hydrogel consisting of GalNAc-sucglu(O-methyl-cyc-pentyl)_2 is stable even under high salt concentrations probably due to its nonionic character and as a result, a native protein is successfully entrapped in the gel matrix without denaturation.
机译：本文描述了用于合成超分子胶凝剂作为新的有机材料的组合方法。在开发人工糖脂的方便且灵活的固相合成过程中，偶然发现其中一些化合物对有机溶剂起着低分子量胶凝剂的作用。使用糖基化氨基乙酸酯的这种组合固相合成，可以有效地进行低分子量有机/水凝胶化剂的筛选和优化。我们发现，添加N-乙酰基-半乳糖胺的氨基酸酯（GalNAc-aa）可有效地凝胶化多种有机溶剂。更有趣的是，某些GalNAc-aa衍生物表现出出色的水凝胶化能力。透射电子显微镜，扫描电子显微镜，共聚焦激光扫描显微镜和FT-IR用于表征凝胶结构。结果表明，由强氢键网络支撑的超分子纤维被缠结在一起，因此所形成的空间可以有效地固定许多溶剂分子。此外，由GalNAc-sucglu（O-甲基-cyc-戊基）_2组成的超分子水凝胶即使在高盐浓度下也很稳定，这可能是由于其非离子特性，结果是天然蛋白被成功地包埋在凝胶基质中，而没有变性。

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