Peptoids and Polypeptoids at the Frontier of Supra- and Macromolecular Engineering

Gangloff, Niklas; Ulbricht, Juliane; Lorson, Thomas; Schlaad, Helmut; Luxenhofer, Robert

doi:10.1021/acs.chemrev.5b00201

Cited by 229 publications

(208 citation statements)

References 404 publications

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“…poly(E-N-benzyloxycarbonyl-L-lysine), [99] poly(g-benzyl-L-glutamate), [99] poly(g-tert-butyl-L-glutamate), [100] and poly(S-ethylsulfonyl-L-cystine)], [101] PNMG-b-poly(E-caprolactone), [102] PNMG-b-poly[2-(3-butenyl)-2-oxazoline], [57] PNMG-b-(Leu-Aib) n [(Leu-Aib) n : helical peptides], [103][104][105][106][107][108][109][110] PNMG-b-poly(L-lactide) (AB, A 2 B, A 3 B types), [111] dextran-b-PNMG, [112] PEG-b-PNMG, [42] and C n512-18 -PNMG lipopolymers. [113][114][115] Their solution aggregation behavior has been reviewed by Luxenhofer et al [30] and will not be repeated here. We will highlight several recent examples of block copolypeptoid-based solution aggregates, particularly those that exhibit stimuli-responsive characteristics in dilute or semidilute solutions.…”

Section: Immunogenicitymentioning

confidence: 96%

“…[90,96] 30 ] were rapidly captured by the liver upon second administration [97] and cleared from the bloodstream, whereas the micelles to that of at the first administration. [90] This has been attributed to the significantly reduced interaction of the micelles with densely grafted polysarcosine corona with the B lymphocyte receptors and hence the suppression of antibody production.…”

Section: Immunogenicitymentioning

confidence: 99%

“…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 chapter is not meant to give a comprehensive review of the research activities in the field. It will focus on the recent development in the synthetic methods to access polypeptoid polymers with well-defined structures and highlight some of the fundamental physicochemical and biological…”

Section: Introductionmentioning

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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Section: Immunogenicitymentioning

confidence: 96%

Section: Immunogenicitymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Polypeptoid polymers: Synthesis, characterization, and properties

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“…Due to the consequent lack of the polar N–H bonds, their lipophilicity is increased, which may result in improved membrane permeability [16–17]. Furthermore, peptoids have also found utility in supra- and macromolecular engineering [18] and polymer chemistry [19]. Nevertheless, the lack of constraints in peptoids may result in a lower affinity for macromolecular targets, which limits their utility [20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of acylhydrazino-peptomers, a new class of peptidomimetics, by consecutive Ugi and hydrazino-Ugi reactions

Barreto

Santos

Andrade

2016

Beilstein J. Org. Chem.

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Herein we describe a versatile approach for the synthesis of acylhydrazino-peptomers, a new class of peptidomimetics. The key idea in this approach is based on a simple route using a one-pot hydrazino-Ugi four-component reaction followed by a hydrazinolysis or hydrolysis reaction and subsequent hydrazino-Ugi reaction or classical Ugi reaction for the construction of acyclic acylhydrazino-peptomers. The consecutive multicomponent reactions produced a variety of acylhydrazino-peptomers in moderate to excellent yields (47–90%). These compounds are multifunctional intermediates that can be further functionalized to obtain new peptidomimetics with potential biological activity.

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“…1,2 Peptoids are a class of robust, informationrich, chemically-diverse peptidomimetic polymers composed of N-substituted glycine monomers. 3 Like peptides, they have the ability to adopt distinct secondary structures such as ribbons, 4 helices, 5,6 sheets, 7 turns, 8 and cyclic structures; 9,10 however, the lack of a backbone hydrogen bond donor (NH) and chirality forces peptoid oligomers to conform to different folding rules as compared to their peptide counterparts. 11 Peptoids can be engineered to adopt multiple two and three-dimensional supramolecular assemblies including superhelices, 12 multi-helical bundles 13,14 and two-dimensional nanosheets.…”

mentioning

confidence: 99%

Improved chemical and mechanical stability of peptoid nanosheets by photo-crosslinking the hydrophobic core

et al. 2016

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Peptoids and Polypeptoids at the Frontier of Supra- and Macromolecular Engineering

Abstract: Scheme 3. Different Approaches Toward (Poly)(β-peptoid)s that Have Been Described in Literature a a Reprinted with permission from ref 39.

Cited by 229 publications

References 404 publications

Polypeptoid polymers: Synthesis, characterization, and properties

Polypeptoid polymers: Synthesis, characterization, and properties

Synthesis of acylhydrazino-peptomers, a new class of peptidomimetics, by consecutive Ugi and hydrazino-Ugi reactions

Improved chemical and mechanical stability of peptoid nanosheets by photo-crosslinking the hydrophobic core

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