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Progress in Chemistry 2019, Vol. 31 Issue (12): 1623-1636 DOI: 10.7536/PC190446 Previous Articles   Next Articles

Supramolecular Chiral Self-Assembly of Peptides and Its Applications

Daiwu Lin1, Qiguo Xing1, Yuefei Wang1,**(), Wei Qi1,2, Rongxin Su1,2, Zhimin He1   

  1. 1. State Key Laboratory of Chemical Engineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China
    2. The Co-Innovation Center of Chemistry and Chemical Engineering of Tianjin, Tianjin 300072, China
  • Received: Online: Published:
  • Contact: Yuefei Wang
  • About author:
    ** E-mail:
  • Supported by:
    National Natural Science Foundation of China(21621004); National Natural Science Foundation of China(21606166); National Natural Science Foundation of China(51773149)
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Chiral self-assembly of peptides is an important way to prepare chiral nanomaterials, including nanohelices, nanotubes and chiral hydrogels. The self-assembled chiral nanomaterials with unique biological and optical activities have important applications in the fields of biology, chemistry, medicine and materials science. Although many chiral nanomaterials have been designed and synthesized based on the self-assembly of peptides, the precise control of their chiral assembly process and their chirality is still a challenge. This paper focuses on the design of peptide molecules and the regulation strategies for peptide chiral self-assembly, including the regulation of internal factors such as the amino acid sequences and configuration of polypeptide molecules, and the regulation of external factors such as pH, solvents and additives. Moreover, the applications of peptide-based chiral nanomaterials in the fields of chiral catalysis, chiral sensing, template synthesis and chiroptics are also reviewed.

Key words: peptides, chiral self-assembly, structural manipulation, chiral catalysis, chiral sensing, chiral templates, chiroptics
Fig. 1 (a) Molecular structures and self-assembly structures of tetrapeptide amphiphiles[38]; (b) Schematic illustration showing the chiral self-assembly of Fmoc-tripeptide into chiral nanostructures with different chirality[42]
Fig. 2 Schematic illustration showing the effect of electrostatic interaction on hexapeptide self-assembly process[43]
Fig. 3 The schematic illustration of chiral self-assembly of enantiomeric short amphiphilic peptides[46]
Fig. 4 Schematic illustration showing the self-assembly process of enantiomer polypeptides[51,52].(a) Atomic force microscopic images showing the triblock-type peptides composed of L- or D-amino acid self-assemble into different nanostructures;(b) Schematic and TEM images showing the enantiomeric Ac-(FKFE)2-NH2 peptides assemble into β-sheet nanoribbons(1) or self-sorted enantiomeric nanohelices(2)
Fig. 5 Schematic illustration of the chiral self-assembly of amyloid fibrils at different pH[53]
Fig. 6 TEM images(a~h) and schematic illustration(i) of the chiral nanostructures self-assembled by S233HisL12 and S263His2L12 at different pH[54]. The molecular assemblies were prepared from S263His2L12 in 10 mM TBS(pH=7.4, a and b) and 10 mM CBS(pH=5.0, c and d; pH=3.0, e and f); The molecular assemblies were prepared from S233HisL12 in 10 mM CBS(pH=3.0, g and h)
Fig. 7 Schematic illustration of dynamic chirality inversion of self-assembled Fmoc-FWK nanostructures induced by pH[56]
Fig. 8 (a) Molecular design of small-molecular gelators and (b) photographs showing the gel formation of G1~G8 in ethanol after ultrasonic treatment[58]
Fig. 9 (a) Photo images of the 4BLGA gels with different metal ions and the SEM images of helical nanofibers formed by 4BLGA with different metal ions[60];(b) Nanostructures assembled from L-type enantiomeric monomers(LPF and LPPG) with different metal ions[61]
Fig. 10 Schematic illustration showing helical nanofibers of Fc-FF with different counterions[64]
Fig. 11 (a) Molecular structures of the designed Azo-GFGH and the photo-switchable assembly and the catalytic properties of the peptide-based hydrolase mimic[66];(b) Description of Photo-response Characteristics of Supramolecular Assembly of Cationic Phenylalanine Dipeptide and Azobenzene Derivative[67];(c) Synthesis of fluorescent hollow nanocapsule and free-standing thin lamella film by tyrosine-tyrosine UV crosslinking[68]
Fig. 12 (a) Cryo-TEM images and schematic illustration of the self-assembled helical assemblies of the peptide amphiphile at different time[73];(b) Cryo-TEM images and schematic illustration of pathway to nanotubes by chiral C12-β12 self-assembly[74]
Fig. 13 (a) The schematic illustration of self-assembly of vesicles and the model for the aldol reaction[75];(b) The schematic illustration of chiral nanotubes formed by Pro-Lys dipeptide derivative[76]
Fig. 14 The schematic illustration of the assembly mechanism of(a) Cu(Ⅱ)-HN catalysis and its asymmetric catalysis for Diels-Alder reaction and(b) Bi(Ⅲ)-HN catalysis and its asymmetric catalysis for Mukaiyama Aldol reaction[35,77]
Fig. 15 The illustration showing visualized recognition functions of amphiphilic peptides[78,79]
Fig. 16 (a) The illustration showing self-assembly of racemic alanine derivatives and its capacity for the discrimination of chiral species[80]; (b) The assembly mechanism of new amphiphilic gelators with different metal ions[81]
Fig. 17 The mechanism illustration of the formation of chiral silica nanostructures[83,84]
Fig. 18 (a) Schematic diagram of cysteine-controlled synthesis of chiral gold nanoparticles[86];(b) The illustration of Au-nanoparticle synthesis and chiral self-assembly strategy[87]
Fig. 19 (a) Self-assembly of Fmoc-Glu and purine nucleosides into helical structures and chiral transfer from Fmoc-Glu to ThT[90];(b) Chiral Induction of Fluorescent Dyes by Glutamic Acid Derivatives as Nanotemplates[91]
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