Synthesis and Characterization of Cyclic Brush-Like Polymers by N-Heterocyclic Carbene-Mediated Zwitterionic Polymerization of N-Propargyl N-Carboxyanhydride and the Grafting-to Approach

Lahasky, Samuel H.; Serem, Wilson K.; Guo, Li; Garno, Jayne C.; Zhang, Donghui

doi:10.1021/ma201948u

Cited by 100 publications

(100 citation statements)

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“…In particular, the successful preparation of a pentablock quinquiespolymer highlighted the unique character of the NNCA NuLROP [23]. Moreover, efficient polymer analogue modification [24,25] and thermo-responsiveness [26,27] of polypeptoids was described.…”

Section: Open Accessmentioning

confidence: 99%

Thermal Properties of Aliphatic Polypeptoids

Fetsch

Luxenhofer

2013

Polymers

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A series of polypeptoid homopolymers bearing short (C 1 -C 5 ) side chains of degrees of polymerization of 10-100 are studied with respect to thermal stability, glass transition and melting points. Thermogravimetric analysis of polypeptoids suggests stability to >200 °C. The study of the glass transition temperatures by differential scanning calorimetry revealed two dependencies. On the one hand an extension of the side chain by constant degree of polymerization decrease the glass transition temperatures (T g ) and on the other hand a raise of the degree of polymerization by constant side chain length leads to an increase of the T g to a constant value. Melting points were observed for polypeptoids with a side chain comprising not less than three methyl carbon atoms. X-ray diffraction of polysarcosine and poly(N-ethylglycine) corroborates the observed lack of melting points and thus, their amorphous nature. Diffractograms of the other investigated polypeptoids imply that crystalline domains exist in the polymer powder.

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Section: Open Accessmentioning

confidence: 99%

Thermal Properties of Aliphatic Polypeptoids

Fetsch

Luxenhofer

2013

Polymers

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“…The reactions proceed in a controlled manner in SCHEME 5 ROPs of R-NTAs using rare earth metal borohydrides or primary amine initiators to produce polypeptoids or their copolymers SCHEME 6 Aminoalcohol-initiated ROP of R-NTAs (R@Me, Et) to produce telechelic polypeptoids [5,6] and cyclic random and block copolypeptoids. [15,37,67,68] Bu-NCA similar to NHCs (Scheme 8). [69] The reaction occurs in a controlled manner in low dielectric solvents (eg, THF and toluene), allowing access of polypeptoids having low to medium molecular weights (DP < 300) and narrow PDI (1.02-1.12), similar to what has been reported for NHCs.…”

Section: Synthesis Of Linear Polypeptoidsmentioning

confidence: 99%

“…[68] Adapted with permission from American Chemical Society mers bearing an internal poly(L-lysine) and an external polysarcosine block using polymeric macroinitiators having primary amino groups on the sidechains. [72] The cationic bottlebrush polymers were examined as effective carriers for siRNA delivery with a 70% knock down efficiency of ApoB100 mRNA in AM L-12 hepatocytes.…”

Section: Fig Urementioning

confidence: 99%

“…[77] Adapted with permission from John Wiley and Sons copolymer than the PNPgG homopolymer. [68] This was attributed to the strong tendency of PNPgG to aggregate in solution, limiting the access of the propargyl groups by the azide and Cu catalyst. Schlaad et al also reported that the resulting triazole moieties can be further quaternized with alkyl bromide to produce a polypeptoid ionic liquid (Scheme 9).…”

Section: Postpolymerization Modification Of Polypeptoidsmentioning

confidence: 99%

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Polypeptoid polymers: Synthesis, characterization, and properties

et al. 2017

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Polypeptoids, a class of peptidomimetic polymers, have emerged at the forefront of macromolecular and supramolecular science and engineering as the technological relevance of these polymers continues to be demonstrated. The chemical and structural diversity of polypeptoids have enabled access to and adjustment of a variety of physicochemical and biological properties (eg, solubility, charge characteristics, chain conformation, HLB, thermal processability, degradability, cytotoxicity and immunogenicity). These attributes have made this synthetic polymer platform a potential candidate for various biomedical and biotechnological applications. This review will provide an overview of recent development in synthetic methods to access polypeptoid polymers with well-defined structures and highlight some of the fundamental physicochemical and biological properties of polypeptoids that are pertinent to the future development of functional materials based on polypeptoids. | I N TR ODU C TI ONPolypeptoids composed of N-substituted polyglycine backbones are structural mimics of polypeptides ( Figure 1). Because of N-substitution, polypeptoids lack stereogenic centers and hydrogen bonding interactions along the main chains, in sharp contrast to polypeptides.As a result, the global conformations of polypeptoids are strongly dependent on the N-substituent structures, giving rise to random coils or well-defined secondary structures [eg, polyproline I (PPI) helix [1][2][3][4][5][6] and R-sheets] [7][8][9][10][11][12] that are reminiscent of those of polypeptides. The polypeptoid backbone containing tertiary amide linkages is highly polar and hydrophilic. The physicochemical properties of polypeptoids can be tailored by the N-substituent structures, enabling control over the hydrophilicity and lipophilicity balance (HLB), charge characteristics, [13,14] backbone conformation, [1][2][3][4][5][6][7][8][9][10][11][12] solubility, [15][16][17][18][19][20] thermal and crystallization properties of the polypeptoids. [21][22][23][24] Without extensive hydrogen bonding, polypeptoids are thermally processable similar to conventional thermoplastics, [20][21][22][23][24] whereas polypeptides undergo thermal degradation before they can be melt-processed due to the extensive hydrogen bonding interactions. While polypeptoids exhibited enhanced proteolytic stability relative to peptides, [25,26] they can be oxidatively degraded under conditions that mimic tissue inflammation, [27] suggesting their potential in vivo uses as biodegradable materials.Recent advances in the controlled polymerization methods have enabled access to a suite of structurally well-defined polypeptoids with various N-substituent structures and molecular architectures, setting the stage for the future development of polypeptoid materials for various targeted applications. Several review articles on the synthesis, properties, and application of polypeptoids for biomedical or nonbiomedical uses have been published in recent years. [28][29][30][31][32] As a result, this...

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“…50 Peptoid macrocycles with alkyne-terminated sidechains have also been synthesized by both the submonomer protocol 51 and NCA polymerization. 52 Depending on the sequence, the macrocycles could crystallize and adopt two interconvertable conformations and reversibly sequester water. cell-based assay for screening vascular endothelial growth factor receptor 2 (VEGFR2)-binding peptoids that could potentially be adapted for biomaterials discovery.…”

Section: Clickable Multivalent Scaffoldsmentioning

confidence: 99%

Peptoids for biomaterials science

Lau

2014

Biomater. Sci.

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The Strathprints institutional repository (https://strathprints.strath.ac.uk) is a digital archive of University of Strathclyde research outputs. It has been developed to disseminate open access research outputs, expose data about those outputs, and enable the management and persistent access to Strathclyde's intellectual output. Peptoids for Biomaterials ScienceKing Hang Aaron Lau* a Poly(N-substituted glycine) ÒpeptoidsÓ have conventionally been exploited for drug discovery and therapeutics due to their structural similarity to peptides, protease resistance, and relative ease of synthesis. This mini-review highlights recent reports of peptoid selfassembled nanostructures and macromolecular interfaces relevant to biomaterials science. The results illustrate how the versatility of peptoid design and synthesis could be exploited to generate multifunctional, modular and precisely tunable biointerfaces and biomaterials.

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Synthesis and Characterization of Cyclic Brush-Like Polymers by N-Heterocyclic Carbene-Mediated Zwitterionic Polymerization of N-Propargyl N-Carboxyanhydride and the Grafting-to Approach

Cited by 100 publications

References 65 publications

Thermal Properties of Aliphatic Polypeptoids

Thermal Properties of Aliphatic Polypeptoids

Polypeptoid polymers: Synthesis, characterization, and properties

Peptoids for biomaterials science

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