Design of Achiral Peptides with a Terminal Functional Group and Their Helicity Induction

非共价手性多米诺效应(NCDE)是一种作用于螺旋肽上的新型手性相互作用。根据NCDE原理，光学非活性螺旋多肽在N-末端进行手性识别。随后，获得的手性信号沿着单链转移到C-末端，就像是多米诺骨牌倒塌一样，最终导致诱导出过量的单手螺旋。本课题的研究成果总结如下：(1)多肽骨架的设计：设计了一个由非编码残基组成的光学非活性多肽螺旋，并对其固体结构进行了研究。这种类型的多肽表现出强烈的采用典型的3-螺旋的倾向。(2)通过NCDE诱导螺旋性：从(1)得到的一种N-末端自由的多肽通过添加手性酸来诱导单手螺旋。(3)手性多肽的螺旋结构的控制：NCDE被证明能够控制起始的…。手性多肽的更多的L螺旋性和螺旋稳定性。(4)产生NCDE的立体化学：根据提出的NCDE的机制，3&lt；10&GT的N-末端片段；-Helix本身具有两个游离的酰胺类NHS，通过多点相互作用容易捕获外部分子来识别手性。(5)通过共价手性相互作用诱导螺旋性：根据手性序列与所产生的螺旋性之间的关系，提出了每个氨基酸残基的螺旋感觉偏好。(6)具有官能团的脱氢肽的构象分析：这些结果为基于多肽的手性功能器件的设计开辟了道路。(7)通过多维多米诺骨牌效应在水中进行手性诱导：由光学非活性多肽组成的胶束经历了手性诱导，并在多肽分子之间产生了高度不对称的空间。这一发现可能会导致基于非手性多肽支架的新型手性功能器件的制备。综上所述，该项目的成果在广泛的聚合物和化学领域具有重要的学术意义和实用价值。较少

The noncovalent chiral domino effect (NCDE) was proposed here as novel chiral interaction operating on a helical peptide. According to the NCDE principle, an optically inactive helical peptide undergoes chiral recognition at the N-terminus. Subsequently, the chiral signal acquired therein transfers to the C-terminus along the single chain, as if it is "domino toppling", finally leading to induction of excess of a one-handed helix. The results of the present project are summarized as follows.(1) Design of peptide backbone : An optically inactive peptide helix composed of non-coded residues was designed, and the solid-sate structure was investigated. This type of peptides shows a strong tendency to adopt a typical 3_<10>-helix.(2) Induction of helicity through NCDE : An N-terminal-free peptide, derived from (1), undergoes the induction of a one-handed helix through addition of chiral acid.(3) Control of helical structure of chiral peptide : NCDE was shown to enable control of the origina … More l helicity and helical stability of chiral peptides.(4) Stereochemistry for generating the NCDE : According to proposed mechanism of the NCDE, the N-terminal segment of a 3_<10>-helix possesses intrinsically two free amide NHs that tend to capture an external molecule through multipoint interaction to recognize the chirality.(5) Helicity induction through covalent chiral interaction : A screw sense preference of each amino acid residue was proposed from the relationship between a chiral sequence and the resulting helicity.(6) Conformational analysis of dehydropeptides having functional groups : These results open up the way to design a chiral functional device based on peptides.(7) Chiral induction in water through multi-D domino effect : A micelle composed of an optically inactive peptide underwent chiral induction, which also generates a highly asymmetrical space between peptide molecules. This finding in future might lead to the fabrication of novel chiral functional devices based on achiral peptide scaffold.In conclusion, the achievement of this project is of academic as well as of practical important in a wide range of polymer and chemistry fields. Less