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Heterochirality Restricts the Self-Assembly of Phenylalanine Dipeptides Capped with Highly Aromatic Groups.
The Journal of Physical Chemistry B ( IF 2.8 ) Pub Date : 2020-06-19 , DOI: 10.1021/acs.jpcb.0c04513 Ana M Gil 1 , Jordi Casanovas 2 , Enric Mayans 3 , Ana I Jiménez 1 , Jordi Puiggalí 3 , Carlos Alemán 3
The Journal of Physical Chemistry B ( IF 2.8 ) Pub Date : 2020-06-19 , DOI: 10.1021/acs.jpcb.0c04513 Ana M Gil 1 , Jordi Casanovas 2 , Enric Mayans 3 , Ana I Jiménez 1 , Jordi Puiggalí 3 , Carlos Alemán 3
Affiliation
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The influence of stereochemistry on the self-assembly of phenylalanine (Phe) dipeptides bearing aromatic fluorenyl groups at both the N- and C-termini (Fmoc, OFm) has been investigated. For this purpose, Fmoc–d-Phe–l-Phe–OFm and Fmoc–l-Phe–l-Phe–OFm have been examined considering a wide variety of solvents, which differ in dielectric constant and volatility. Results reveal that replacement of l-Phe by d-Phe has a major impact on the self-assembly propensities, restricting drastically the structural diversity and polymorphism shown by the homochiral dipeptide. Thus, the analogous heterochiral dipeptide shows a great propensity to form micro/nanofibers, independently of the environmental conditions. Theoretical calculations revealed that the stability of antiparallel disposition is much higher (a factor of ca. 15) for Fmoc–d-Phe–l-Phe–OFm than that for Fmoc–l-Phe–l-Phe–OFm, which has been attributed to the hydrophobic core formed in the former. Overall, results suggest that control of the backbone chirality is a potent and versatile strategy to drive and finely tune the self-assembly propensities of highly aromatic peptides.
中文翻译：
异规性限制了具有高度芳香族基团的苯丙氨酸二肽的自组装。
研究了立体化学对在N-和C-末端（Fmoc，OFm）均带有芳香芴基的苯丙氨酸（Phe）二肽自组装的影响。为了这个目的，将Fmoc -d -Phe-升-Phe-OFM和的Fmoc-升-Phe-升-Phe-OFM已经检验考虑各种各样的溶剂，其在介电常数和挥发性不同的。结果表明，用d替代了l -Phe-苯丙氨酸对自组装倾向具有重大影响，极大地限制了同手性二肽所显示的结构多样性和多态性。因此，与环境条件无关，类似的杂手性二肽显示出形成微/纳米纤维的极大倾向。理论计算表明，反平行配置的稳定性高得多的对的Fmoc-（一个约15的因子）d -Phe-升-Phe-OFM比用于将Fmoc-升-Phe-升-Phe-OFM，这一直归因于在前者中形成的疏水核。总体而言，结果表明，控制主链手性是一种有效且通用的策略，可以驱动和精细调整高度芳香族肽的自组装倾向。
更新日期：2020-07-16
中文翻译：
异规性限制了具有高度芳香族基团的苯丙氨酸二肽的自组装。
研究了立体化学对在N-和C-末端（Fmoc，OFm）均带有芳香芴基的苯丙氨酸（Phe）二肽自组装的影响。为了这个目的，将Fmoc -d -Phe-升-Phe-OFM和的Fmoc-升-Phe-升-Phe-OFM已经检验考虑各种各样的溶剂，其在介电常数和挥发性不同的。结果表明，用d替代了l -Phe-苯丙氨酸对自组装倾向具有重大影响，极大地限制了同手性二肽所显示的结构多样性和多态性。因此，与环境条件无关，类似的杂手性二肽显示出形成微/纳米纤维的极大倾向。理论计算表明，反平行配置的稳定性高得多的对的Fmoc-（一个约15的因子）d -Phe-升-Phe-OFM比用于将Fmoc-升-Phe-升-Phe-OFM，这一直归因于在前者中形成的疏水核。总体而言，结果表明，控制主链手性是一种有效且通用的策略，可以驱动和精细调整高度芳香族肽的自组装倾向。
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