Effect of Molecular Structure on the Properties of Naphthalene-Dipeptide Hydrogelators
Effect of Molecular Structure on the Properties of Naphthalene-Dipeptide Hydrogelators
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DOI：
10.1021/la102059x
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发表时间：
2010-08-17
期刊：
影响因子：
3.9
通讯作者：
Adams, Dave J.
中科院分区：
文献类型：
--
作者：
Chen, Lin;Revel, Steven;Adams, Dave J.
二肽缀合物可以是有效的低分子量水凝胶因子。然而，由于缺乏对控制组装和凝胶化的设计规则的清晰理解，用于特定应用的凝胶因子的有效设计受到损害。在这里，我们报告了萘二肽库，它们的物理化学性质，和凝胶化能力。我们改变了二肽中的氨基酸和萘环上的取代，以允许整个分子的结构变化。我们研究了这些排列的临界胶束浓度和空气-水分配系数在高pH值和表观PLC的影响。我们表明，这些属性和预测的整体共轭物的疏水性之间存在明确的联系，而不是随着例如二肽序列而变化的属性。这些二肽缀合物中的大多数是有效的水凝胶因子，尽管在溶液性质与缀合物是否是水凝胶因子之间没有明显的联系。然而，在发生凝胶化的情况下，疏水性和表观pK（a）之间的联系允许预测将形成凝胶的pH，从而为特定应用选择胶凝剂提供信息。
Dipeptide-conjugates can be efficient low molecular weight hydrogelators. However, the effective design of a gelator for a specific application is compromised by the lack of a clear understanding of the design rules that govern assembly and hence gelation. Here, we report a library of naphthalene-dipeptides, their physical chemical properties, and gelation ability. We have varied both the amino acids in the dipeptides and the substitution on the naphthalene ring to allow variation of the structure throughout the molecule. We have examined the effects of these permutations on the critical micelle concentration and air water partition coefficient at high pH and the apparent plc. We show that there is a clear link between these properties and the predicted hydrophobicity of the overall conjugates, rather than the properties varying with, for example, the dipeptide sequence. The majority of these dipeptide conjugates are effective hydrogelators, although there is no apparent link between the solution properties and whether or not a conjugate is a hydrogelator. Nevertheless, where gelation occurs, the link between hydrophobicity and apparent pK(a) allows the prediction of the pH at which a gel will be formed and hence informed choice of gelator for specific applications.