Synthetic Approach of Thermally Tunable Nature‐Mimetic Polypeptides from <i>N</i>‐Protected Alternating Peptoids

Koyama, Yasuhito; Ihsan, Abu Bin; Gudeangadi, Prashant

doi:10.1002/macp.201800303

Cited by 11 publications

(7 citation statements)

References 33 publications

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“…At this moment, we noticed that the tendency observed in Figure 2c was not dependent only on the difference of secondary structures of the alternating peptides. Aside from the cloud point, the transmittance of Pr-Pep slightly decreased at the higher temperatures compared with that at around 20 °C, implying that the thermal aggregates of hydrophobic side chains would afford an additional cloud point upon heating [23]. The cloud point of Me-Pep appeared at a slightly higher temperature than that of Et-Pep (Figure 5f).…”

Section: Resultsmentioning

confidence: 99%

Effects of the Hydrophilic–Lipophilic Balance of Alternating Peptides on Self-Assembly and Thermo-Responsive Behaviors

Ihsan

Nargis

Koyama

2019

IJMS

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A series of N-substituted poly(Gly–alter–Val) peptides were successfully synthesized for the systematic evaluation of the micellization behavior of alternating peptides. Three-component polymerization employing an aldehyde, a primary ammonium chloride, and potassium isocyanoacetate afforded four alternating peptides in excellent yields. We investigated the dependence of the hydrophilic–lipophilic balance of alternating peptides on the micellization behavior. All the aqueous solutions of alternating peptides exhibited upper critical solution temperature (UCST) behaviors, strongly indicating that the alternating binary pattern would mainly contribute to the UCST behaviors. The cloud points of alternating peptides shifted to higher temperatures as the side chains became more hydrophilic, which is opposite to the trend of typical surfactants. Such unusual micellization behaviors appeared to be dependent on the quasi-stable structure of single polymer chains formed in water.

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Section: Resultsmentioning

confidence: 99%

Effects of the Hydrophilic–Lipophilic Balance of Alternating Peptides on Self-Assembly and Thermo-Responsive Behaviors

Ihsan

Nargis

Koyama

2019

IJMS

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“…The mixture was stirred for 6 days at room temperature, quenched with water, and purified to obtain the MPE-substituted poly(Orn-alter-Gly). [25][26][27][28] MPE-substituted poly(Orn-alter-Gly) (0.3 g) was dissolved in methanesulfonic acid (5 g, 3.4 ml) and stirred at 100 C for 16 h. The product was purified to obtain the poly(Orn-alter-Gly). [25][26][27][28]…”

Section: Synthesis Of Poly(orn-alter-gly)mentioning

confidence: 99%

“…[25][26][27][28] MPE-substituted poly(Orn-alter-Gly) (0.3 g) was dissolved in methanesulfonic acid (5 g, 3.4 ml) and stirred at 100 C for 16 h. The product was purified to obtain the poly(Orn-alter-Gly). [25][26][27][28]…”

Section: Synthesis Of Poly(orn-alter-gly)mentioning

confidence: 99%

A cationic alternating copolymer composed of ornithine and glycine with an ordered sequence for enhanced bacterial activity

Liu

et al. 2021

Polymer Engineering & Sci

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The chains and segments of unordered cationic polypeptides are complex and may produce unexpected biological activities. Herein, the Ugi's 4CC reaction is adopted to synthesize a cationic alternating copolymer comprising ornithine and glycine (poly(Orn-alter-Gly)) with an ordered sequence for enhanced bacterial resistance. In this technique, potassium isocyanate, 4-(N-carbobenzyloxyamino)-1-butyraldehyde and 1-(4-Methoxyphenyl)ethylamine react to produce MPEsubstituted poly(Orn-alter-Gly) in one step without using a catalyst and then poly(Orn-alter-Gly) is obtained by removing the N-(1-p-methoxyphenethyl) (MPE) group. 1 H NMR, Fourier transform infrared spectroscopy, and automatic amino acid analysis confirm that ornithine and glycine are linked alternately in the poly(Orn-alter-Gly) chains. Both MPE-substituted poly(Orn-alter-Gly) and poly(Orn-alter-Gly) have excellent antibacterial activity against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa as well as excellent biocompatibility. The synthesis strategy and materials provide new information on how to obtain ordered sequence cationic polypeptides.

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“…The amino acid alternating copolymer is a kind of alternated polymer composed of two different amino acids . They have regular sequences and consistent degradation fragments, and their properties can be regulated by macromolecular chain sequences and side groups, which have prospects for application in the biomedical field. − To exemplify, Charles J. Bowerman et al constructed a variety of alternate amino acid copolymers that could be used for self-assembly and hydrogel preparation, such as Ac-(XKXK) 2 -NH 2 peptides, where X = valine (Val), isoleucine (Ile), phenylalanine (Phe), pentafluorophenylalanine (F5-Phe), and cyclohexylalanine (Cha) . In our previous work, we prepared alkaline alternating amino acid copolymers and further modified the surface of biomaterials to obtain higher biocompatible and antibacterial properties. , Solid-phase peptide synthesis (SPPS) technology allows efficient and precise preparation of target peptides, which is beneficial to accurately control the side chain groups and molecular weight. − …”

Section: Introductionmentioning

confidence: 99%

Alkaline Amino Acid Alternating Copolymers with Potent Antibacterial Properties for the Treatment of Periodontitis

Shao

et al. 2023

ACS Appl. Polym. Mater.

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Although antibacterial peptides with excellent properties emerge endlessly, the antibacterial peptides with alternating structures have not attracted much attention. In this work, three amino acid alternating copolymers (Orn-Ser, Orn-Gly, and Orn-Val) with similar molecular weights but different hydrophilicity were constructed for the study of antibacterial properties through the solid-phase peptide synthesis (SPPS) method. We found that these three amino acid alternating copolymers showed excellent biocompatibility and broad spectrum antibacterial activity. Nevertheless, they showed slightly different properties due to differences in hydrophilicity and cationic density, for instance, better biocompatibility of Orn-Ser, stronger antibacterial property of Orn-Gly, and a higher selectivity index of Orn-Val. In a rat periodontitis model, Orn-Gly and Orn-Val exhibited remarkable anti-infective performance and significant therapeutic effects. This work is expected to play an important role in the treatment of periodontitis and the rational design of antimicrobial peptides for different applications.

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Synthetic Approach of Thermally Tunable Nature‐Mimetic Polypeptides from N‐Protected Alternating Peptoids

Cited by 11 publications

References 33 publications

Effects of the Hydrophilic–Lipophilic Balance of Alternating Peptides on Self-Assembly and Thermo-Responsive Behaviors

Effects of the Hydrophilic–Lipophilic Balance of Alternating Peptides on Self-Assembly and Thermo-Responsive Behaviors

A cationic alternating copolymer composed of ornithine and glycine with an ordered sequence for enhanced bacterial activity

Alkaline Amino Acid Alternating Copolymers with Potent Antibacterial Properties for the Treatment of Periodontitis

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