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首页> 外文期刊>Chemistry: A European journal >Effect of Structural Modifications on the Self-Assembly of Oligoprolines Conjugated with Sterically Demanding Chromophores
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Effect of Structural Modifications on the Self-Assembly of Oligoprolines Conjugated with Sterically Demanding Chromophores

机译：结构修饰对寡聚脯氨酸与立体要求高的发色团结合的自组装的影响

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摘要

Conjugates between oligoprolines and sterically demanding perylene monoimides (PMIs) form hierarchical supramolecular self-assemblies. The influence of the length and stereochemistry at the attachment site between the peptide backbone and the chromophore on the self-assembly properties of the conjugates was explored. Comparison between oligoprolines bearing 4R- or 4S-configured azidoprolines (Azp) for the conjugation with the PMIs revealed that diastereoisomers with 4R configuration guide the self-assembly consistently better than conjugates with 4S configuration. Elongating the peptide chain beyond nine proline residues or introducing structural errors, by altering the absolute configuration of one stereogenic center at the outside of the functionalizable oligoproline helix, lowered the efficacy of self-assembly significantly, both in solution phase and in the solid state. The results showed how subtle structural modifications allow for tuning the self-assembly of chromophores and provided further design principles for the development of peptide-chromophore conjugates into nanostructured materials.
机译：低聚脯氨酸和空间上要求的per单酰亚胺（PMI）之间的缀合物形成分层的超分子自组装体。探讨了肽骨架和发色团之间的连接位点的长度和立体化学对缀合物自组装性能的影响。带有4R或4S构型叠氮脯氨酸（Azp）的寡脯氨酸与PMI缀合的比较表明，具有4R构型的非对映异构体始终比具有4S构型的缀合物更好地引导自组装。通过改变功能性寡脯氨酸螺旋外部的一个立体生成中心的绝对构型，将肽链延长至超过九个脯氨酸残基或引入结构错误，无论是在溶液阶段还是在固态，都显着降低了自组装的功效。结果表明，微妙的结构修饰如何调节发色团的自组装，并为将肽-发色团结合物发展为纳米结构材料提供了进一步的设计原理。

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