Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS), Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
Org Biomol Chem. 2019 Feb 13;17(7):1984-1991. doi: 10.1039/c8ob02243g.
Linear peptide amphiphiles are excellent biocompatible scaffolds for the hierarchical self-assembly of one-dimensional nano-structures in aqueous media. However, their structural exploration and screening of self-assembling properties are often limited by time-consuming synthesis and purification steps. We here describe the application of an oxime bond as a powerful synthetic tool towards the conjugation of peptide heads bearing a hydroxylamine group with hydrophobic aldehyde tails. This methodology allowed the quick preparation of a small library of oxime-connected peptide amphiphiles, whose supramolecular screening revealed nano-to-micro-fibrillation with dependency on their chemical structure. These results demonstrate the simplicity and the synthetic potential of the oxime conjugation for the preparation of peptide amphiphiles with improved self-assembling capabilities.
线性肽两亲物是在水介质中进行一维纳米结构分级自组装的极好的生物相容性支架。然而，它们的结构探索和自组装性能的筛选通常受到耗时的合成和纯化步骤的限制。我们在这里描述了肟键作为一种强大的合成工具在将带有羟胺基团的肽头与疏水醛尾连接中的应用。该方法允许快速制备一小部分肟连接的肽两亲物文库，其超分子筛选结果表明，其纳米到微纤维化取决于它们的化学结构。这些结果表明肟键连接在制备具有改进的自组装能力的肽两亲物方面的简单性和合成潜力。
