Chiral self-assembly of peptides: Toward the design of supramolecular polymers with enhanced chemical and biological functions

Shen, Yanchun; Wang, Yuefei; Hamley, Ian W.; Qi, Wei; Su, Rongxin; He, Zhimin

doi:10.1016/j.progpolymsci.2021.101469

Cited by 59 publications

(46 citation statements)

References 284 publications

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“…Synthesis of Fc-L F L F. Ferrocene-L-diphenylalanine (ferrocene-L-Phe-L-Phe-COOH, Fc-L F L F) (over 98% purity) was synthesized in the laboratory with reference to the published literature of our group. 1 At room temperature, Fc-L F L F was accurately weighed at 2.62 mg and added in 1 mL of ultrapure water, and 0.5 mol/L aqueous NaOH solution was added drop by drop and shaken to obtain the aqueous solution of Fc-L F L F with pH = 7.2−7.3. The concentration of each Fc-L F L F solution was 5 mM.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Inspired by helical structures in nature, short peptides are used as chiral building blocks to self-assemble into a variety of artificial nanostructures with supramolecular or nanoscale chirality, showing potential applications in chemistry and biomedicine. − The peptides can be chirally self-assembled through non-covalent interactions (including π–π stacking, hydrogen bonding, van der Waals interactions, host–guest interactions, and metal coordination). However, the use of non-covalent interactions to control the self-assembly of peptides remains challenging, especially for the precise control of their multistage chiral structures.…”

Section: Introductionmentioning

confidence: 99%

“…Ferrocene (Fc)-modified peptides have attracted great interest due to their intrinsic redox activity and the ability to assemble into various functional nanostructures, including nanoparticles, chiral nanostructures, , hydrogels, and nanoarrays . In this study, we investigate the coordination assembly of the ferrocene–diphenyalanine (Fc- L F L F) with metal ions by adding different transition-metal ions during the self-assembly process.…”

Section: Introductionmentioning

confidence: 99%

“…21,22 Ferrocene (Fc)-modified peptides have attracted great interest due to their intrinsic redox activity and the ability to assemble into various functional nanostructures, including nanoparticles, 23 chiral nanostructures, 24,25 hydrogels, 26 and nanoarrays. 1 In this study, we investigate the coordination assembly of the ferrocene−diphenyalanine (Fc-L F L F) with metal ions by adding different transition-metal ions during the self-assembly process. The structure and handedness of the peptide assemblies can be controlled precisely by using metal ions, leading to the formation of various chiral nanostructures, including helical microflowers and right-or left-handed nanohelices (Scheme 1).…”

Section: ■ Introductionmentioning

confidence: 99%

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Coordination-Induced Self-Assembly of a Dipeptide into Multifunctional Chiral Nanostructures

et al. 2022

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Short peptides could be used as chiral motifs to self-assemble into various artificial nanostructures with supramolecular or nanoscale chirality, but their applications still need to be expanded. Here, under the mediation of metal ions, the ferrocene–diphenylalanine (Fc-LFLF) peptide can self-assemble into various chiral nanostructures, including right-handed helical microflowers mediated by Cu2+, left-handed nanofibers mediated by Ag+, and right-handed nanofibers mediated by Zn2+ and Cd2+. Meanwhile, the gold nanoparticles could be mineralized and deposited on Cu2+/Fc-LFLF microflowers to form AuNPs@Cu2+/Fc-LFLF, which showed significantly improved catalytic activity. The Ag+ could be further mineralized on the peptide nanofibers to form AgNPs@Fc-LFLF, showing an excellent antibacterial effect. Overall, this study provides new insights into the chiral self-assembly of short peptides and demonstrates that the chiral peptide–metal assemblies may have broad prospects in the fields of biocatalysis and antimicrobials.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Coordination-Induced Self-Assembly of a Dipeptide into Multifunctional Chiral Nanostructures

et al. 2022

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“…Chirality, as a fundamental attribute of nature, is ubiquitous from the molecular to macroscopic level. 1,2 Since the signi cance of stereochemistry in biochemical environments was discovered by Pasteur in 1858, chirality has become a hot issue especially in the biological system, which attracted the attention of researchers in chemistry, materials, and biology. 3,4 The study of chiral phenomena is not only of great signi cance to research elds such as catalysis, synthesis and separation, but also has important scienti c and practical value to other scienti c elds such as life science, pharmaceutical science, and material science.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic polymerization of enantiomeric DOPA into films with enhanced rigidity and stability

Shen

Hao

et al. 2022

Preprint

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L-3,4-dihydroxyphenylalanine (L-DOPA) is an important molecule in the adhesion of mussels, and as an oxidative precursor of natural melanin, it plays an important role in living system. However, the effect of chirality of DOPA monomers on its polymerization and adhesion is still unclear. Here, we investigated the effect of the molecular chirality of DOPA on the properties of the self-assembled films by tyrosinase-induced oxidative polymerization. The kinetics and morphology of pure enantiomers is completely altered upon their co-assembly, allowing the fabrication of layer-to-layer stacked nanostructures and films with improved structural and thermal stability. The different molecular arrangements and self-assembly mechanisms of the L+D-racemic mixtures, whose oxidation products have both increased molecular weight and binding energy, resulting in stronger intermolecular forces and more ordered sheet-stacking arrangements. This leads to the formation of films with a Young's modulus as high as 139 GPa, which is the highest value reported so far for biological materials. This study provides a simple pathway for the fabrication of biomimetic polymeric materials with enhanced physicochemical properties by control the chirality of monomers.

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Supramolecular chiral polymeric aggregates: Construction and applications

et al. 2022

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Inspired by the mystery of natural homochirality, the design and construction of artificial chiral systems with special functions including mechanics, chiroptical devices, and chiral separation have aroused the great interest of scientists. Due to its diverse conformations and components, polymers become an excellent candidate to construct artificial chiral aggregates, which provides an opportunity to fabricate advanced chiral materials. Herein, in this review, we summarized not only the different strategies for construction and regulation of supramolecular chirality in chiral or achiral polymer systems, mainly including post-assembly and polymerizationinduced chiral self-assembly in chiral polymer systems and several chirality transfer and induction strategies in achiral polymer systems, but also the formation mechanisms of chiral aggregates by the chirality amplification from the molecular level to supramolecular level. Furthermore, we present the typical applications of chiral polymeric aggregates in circularly polarized light emission, chiral recognition and separation, and chiral elastomer. Finally, the current challenges and future directions of chiral polymeric aggregates are also elaborated. K E Y W O R D S aggregates, chiral applications, chiral assembly, chirality, polymers INTRODUCTION OF CHIRALITY Chirality in diverse scalesIn nature, chiral structures are widespread at various hierarchical levels, such as the chiral amino acid molecules, the double-helical structure of DNA biomacromolecules, the helical shape of bacterial flagella, and even the visible plant cane and galaxy (Figure 1). [1,2] Scientists have also been working on mimicking helical phenomena in nature and exploring the mechanism of chiral information transfer and amplification, so as to reveal the origin of life and develop advanced functional materials. [3][4][5][6] According to the assembling structures of chiral substances at the molecular level and above, chirality can generally be divided into molecular chirality, supramolecular chirality, and macrochirality, which isThis is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

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Chiral self-assembly of peptides: Toward the design of supramolecular polymers with enhanced chemical and biological functions

Cited by 59 publications

References 284 publications

Coordination-Induced Self-Assembly of a Dipeptide into Multifunctional Chiral Nanostructures

Coordination-Induced Self-Assembly of a Dipeptide into Multifunctional Chiral Nanostructures

Enzymatic polymerization of enantiomeric DOPA into films with enhanced rigidity and stability

Supramolecular chiral polymeric aggregates: Construction and applications

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