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Effect of Structural Modifications on the Self‐Assembly of Oligoprolines Conjugated with Sterically Demanding Chromophores
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2016-02-17 , DOI: 10.1002/chem.201504952 Urszula Lewandowska 1 , Wojciech Zajaczkowski 2 , Wojciech Pisula 2, 3 , Yingjie Ma 2 , Chen Li 2 , Klaus Müllen 2 , Helma Wennemers 1
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2016-02-17 , DOI: 10.1002/chem.201504952 Urszula Lewandowska 1 , Wojciech Zajaczkowski 2 , Wojciech Pisula 2, 3 , Yingjie Ma 2 , Chen Li 2 , Klaus Müllen 2 , Helma Wennemers 1
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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.
中文翻译：
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
寡聚脯氨酸与空间要求高的per单酰亚胺（PMI）之间的缀合物形成分层的超分子自组装体。探索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。比较带有4 R或4 S构型叠氮脯氨酸（Azp）的寡脯氨酸与PMI的缀合，发现具有4 R构型的非对映异构体始终比具有4 S构架的缀合物更好地引导自组装配置。通过改变功能性寡脯氨酸螺旋外侧的一个立体定位中心的绝对构型，将肽链延长至超过九个脯氨酸残基或引入结构“错误”，从而显着降低了自组装的效率，无论是在溶液相中还是在固体中状态。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-发色团偶联物开发为纳米结构材料提供了进一步的设计原理。
更新日期：2016-02-17
中文翻译：
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
寡聚脯氨酸与空间要求高的per单酰亚胺（PMI）之间的缀合物形成分层的超分子自组装体。探索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。比较带有4 R或4 S构型叠氮脯氨酸（Azp）的寡脯氨酸与PMI的缀合，发现具有4 R构型的非对映异构体始终比具有4 S构架的缀合物更好地引导自组装配置。通过改变功能性寡脯氨酸螺旋外侧的一个立体定位中心的绝对构型，将肽链延长至超过九个脯氨酸残基或引入结构“错误”，从而显着降低了自组装的效率，无论是在溶液相中还是在固体中状态。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-发色团偶联物开发为纳米结构材料提供了进一步的设计原理。
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