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首页> 外文期刊>RSC Advances >Aqueous self-assembly of short hydrophobic peptides containing norbornene amino acid into supramolecular structures with spherical shape
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Aqueous self-assembly of short hydrophobic peptides containing norbornene amino acid into supramolecular structures with spherical shape

机译：含有降冰片烯酸的短疏水肽​​的水性自组装成具有球形的上粥样结构

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摘要

The preparation and self-assembly of short hydrophobic peptides able to solubilize in water through the formation of supramolecular assembly is reported. The two diastereoisomeric pentapeptides AcAla-NRB-Ala-Aib-AlaNH _(2) 1 and 2 containing the two enantiomers of non-proteinogenic norbornene amino acid (NRB) were synthesized in an efficient way and in good yields. They were insoluble in organic solvent, except MeOH and DMSO, but completely soluble in water despite that they are made of hydrophobic amino acids. The formation of a supramolecular assembly in water was assessed by Transmission Electron Microscopy (TEM) and Dynamic Light Scattering (DLS) using 1 and 2 individually or in a mixture. Conformational analysis on the two diastereoisomers, performed in CD _(3) CN, CD _(3) OH and in H _(2) O/D _(2) O, indicated the formation of a stable 3 _(10) -helix structure for both peptides: the helix structure is more stable in CD _(3) CN and CD _(3) OH than in H _(2) O/D _(2) O where a helix/random coil transition was observed. Apparently, the norbornene moiety plays a role in the stabilization, in fact 1 R 2 R 3 R -norbornene AA present in peptide 2 induces a more stable secondary structure with respect to the 1 S 2 S 3 S -isomer present in peptide 1 .
机译：报道了能够通过形成超分子组件中的水中溶解水中的短疏水性肽的制备和自组装。以有效的方式合成含有两种非蛋白原降冰片烯氨基酸（NRB）的两个对映体的两种非对映异构化学肽ACALA-NRB-ALA-AIB-ALANH _（2）1和2。它们不溶于有机溶剂，除了MeOH和DMSO之外，但尽管它们是由疏水性氨基酸制成的完全溶于水。通过单独或在混合物中使用1和2的透射电子显微镜（TEM）和动态光散射（DLS）来评估中分子组装在水中的形成。在CD _（3）CN，CD _（3）OH和H _（2）O / D _（2）O中进行的两个非对映异构体的构象分析，表明形成稳定的3 _（10） - 两种肽的螺旋结构：螺旋结构在CD _（3）CN和CD _（3）oh中更稳定，而不是观察到螺旋/随机线圈转变的H _（2）O / D _（2）O. 。显然，降冰片烯部分在稳定化中发挥作用，实际上，肽2中存在的1 R 2 R-冰片烯AA相对于肽1中存在的1 S 2 S 3 S-MORER诱导更稳定的二级结构。

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