Controlled Assembly of Chiral Structure of Diphenylalanine Peptide

doi:10.6023/A19060241

Acta Chimica Sinica ›› 2019, Vol. 77 ›› Issue (11): 1173-1176.DOI: 10.6023/A19060241 Previous Articles Next Articles

Communication

二苯丙氨酸短肽手性结构的可控组装

李琦^a, 贾怡^a, 李峻柏^a^b*()

^a 中国科学院化学研究所胶体、界面与化学热力学院重点实验室北京 100190
^b 中国科学院大学北京 100049

投稿日期:2019-06-28 发布日期:2019-08-16
通讯作者: 李峻柏 E-mail:jbli@iccas.ac.cn
基金资助:
国家自然科学基金(21433010);国家自然科学基金(21872151);国家自然科学基金(21320102004)

Controlled Assembly of Chiral Structure of Diphenylalanine Peptide

Li Qi^a, Jia Yi^a, Li Junbai^a^b*()

^a Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190
^b University of Chinese Academy of Sciences, Beijing 100049

Received:2019-06-28 Published:2019-08-16
Contact: Li Junbai E-mail:jbli@iccas.ac.cn
Supported by:
the National Natural Science Foundation of China(21433010);the National Natural Science Foundation of China(21872151);the National Natural Science Foundation of China(21320102004)

1. Supporting Information.pdf(166KB)

Abstract

Chirality is ubiquitous in nature and it plays an important role in both biological and material sciences. Inspired by nature, scientists have prepared various chiral structures or hybrid materials by self-assembly of polypeptides, amino acids, carbohydrates and their derivatives. These studies provide a good model for understanding of supramolecular chirality and mimicking the self-assembly of organisms. In the past decade, diphenylalanine (FF) and its derivatives have attracted great attentions and have been substantially studied. FF is derived from the core recognition motif of the Alzheimer's disease β-amyloid polypeptide, and it could readily self-assemble into nanotubes, nanowires, nanovesicles, nanofibers and microtubes. Moreover, the polymorphisms of FF-based assemblies can be easily manipulated by controlling the experimental conditions such as concentrations, solvents, pH and temperatures. However, there is few report on the chiral structures obtained from the self-assembly of FF and its derivatives. In this paper, we selected cationic diphenylalanine peptide (CDP) as the assembly units and have obtained CDP nanofibers and helical fibers in ethanol solution by controlling the aging time. Scanning electron microscope (SEM) and atomic force microscope (AFM) were used to characterize the morphologies of CDP assemblies. The mechanism for the formation of CDP nanofibers and helical fibers in ethanol solution was studied by infrared spectroscopy and circular dichroism spectroscopy. It was found that CDP was first assembled into nanofibers. With the increase of aging time, CDP nanofibers twisted and finally assembled into helical fibers similar to the ropes. Spectral data analysis showed that the transformation of nanofibers into helical fibers was mainly due to the strong electrostatic repulsion between positive charges in adjacent peptide molecules and the β-sheet secondary structure controlled by hydrogen bonding between peptide segments. This work realizes the regulation of supramolecular assembly structure by simply controlling the ripening time, and provides a simple and feasible method for the controlled preparation of supramolecular chiral assembly.

Key words: cationic diphenylalanine, molecular assembly, molecular chirality

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Li Qi, Jia Yi, Li Junbai. Controlled Assembly of Chiral Structure of Diphenylalanine Peptide[J]. Acta Chimica Sinica, 2019, 77(11): 1173-1176.

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Fig. & Tab. 4

Figure 1. Schematic illustration of the self-assembly of CDP in ethanol

Figure 2. Scanning electron microscope (SEM) images of CDP assemblies in ethanol after different aging time: (a, b) 1 day, (c, d) 2 weeks, (e, f) 3 weeks. (g) Atomic force microscope (AFM) image of twisted CDP fibril

Figure 3. (a) Fourier transform infrared (FTIR) spectra of CDP powder and CDP assemblies, (b) is the magnification of (a) in the range of 1800~1200 cm-1

Figure 4. CD spectra of CDP assemblies in ethanol after different aging time: nanofibers (1 day), twisted nanofibers (2 weeks) and helical fibers (3 weeks)

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二苯丙氨酸短肽手性结构的可控组装

Controlled Assembly of Chiral Structure of Diphenylalanine Peptide

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