Are <i>N</i>‐substituted glycine <i>N</i>‐thiocarboxyanhydride monomers really hard to polymerize?

Tao, Xinfeng; Zheng, Biao; Kricheldorf, Hans R.; Ling, Jun

doi:10.1002/pola.28402

Cited by 37 publications

(66 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…By contrast, high molecular weight polypeptoids can be synthesized by controlled ROP of R-NCA or R-NTA monomers using nucleophilic initiators such as primary amines [ 41 , 62 , 66 , 93 ]. A wide variety of R-NCA or R-NTA monomers have been reported for primary amine-initiated ROP of polypeptoids bearing various N-substituents in a one-pot fashion [ 44 , 62 , 65 , 66 , 93 , 94 , 95 , 96 ]. As this review is focused on the solution self-assembly of diblock copolypeptoids bearing alkyl side chains with relatively high molecular weight, we will mainly discuss the polymer synthesis using the controlled ROP method.…”

Section: Polypeptoids Bearing Alkyl Side Chains: Synthetic Methods and Their Phase Behaviormentioning

confidence: 99%

Solution Self-Assembly of Coil-Crystalline Diblock Copolypeptoids Bearing Alkyl Side Chains

Jiang

Zhang

2021

Polymers

View full text Add to dashboard Cite

Polypeptoids, a class of synthetic peptidomimetic polymers, have attracted increasing attention due to their potential for biotechnological applications, such as drug/gene delivery, sensing and molecular recognition. Recent investigations on the solution self-assembly of amphiphilic block copolypeptoids highlighted their capability to form a variety of nanostructures with tailorable morphologies and functionalities. Here, we review our recent findings on the solutions self-assembly of coil-crystalline diblock copolypeptoids bearing alkyl side chains. We highlight the solution self-assembly pathways of these polypeptoid block copolymers and show how molecular packing and crystallization of these building blocks affect the self-assembly behavior, resulting in one-dimensional (1D), two-dimensional (2D) and multidimensional hierarchical polymeric nanostructures in solution.

show abstract

Section: Polypeptoids Bearing Alkyl Side Chains: Synthetic Methods and Their Phase Behaviormentioning

confidence: 99%

Solution Self-Assembly of Coil-Crystalline Diblock Copolypeptoids Bearing Alkyl Side Chains

Jiang

Zhang

2021

Polymers

View full text Add to dashboard Cite

show abstract

“…The block copolymers PMeSPG-b-PSar were synthesized by feeding in sequence MeSPG-NTA and Sar-NTA in amine-initiated polymerizations (Scheme 1, more details in Section 4, SI). 79 The structures of the homopolymer and block copolymers were confirmed by NMR, SEC, and MALDI-TOF S2.…”

Section: Pmespg-b-psarmentioning

confidence: 99%

Oxidation-Sensitive Polymersomes Based on Amphiphilic Diblock Copolypeptoids

et al. 2019

Self Cite

View full text Add to dashboard Cite

Stimuli-responsive polymersomes formed by amphiphilic block copolymers have attracted substantial attention as smart and robust containers for drug delivery and nano/micro-reactors. Bio-sourced amphiphilic diblock copolypeptoids were developed that can self-assemble into oxidation-responsive unilamellar vesicles. These vesicles can burst under the action of reactive oxygen species which can be the hydrogen peroxide, or the singlet oxygen produced by light-activation of photosensitizer with spatiotemporal control.Polysarcosine (PSar, also called poly(N-methyl glycine)) was selected as the hydrophilic block, due to its resistance to protein adsorption and low toxicity, similar to PEG. We designed and synthesized poly(N-3-(methylthio)propyl glycine) as the hydrophobic block. Its polyglycine backbone is the same as that of PSar, and especially its hydrophobic N-substituents, thioether side-chains, can be oxidized to hydrophilic sulfoxides. These oxidation-responsive polymersomes entirely based on N-substituted poly(amino acid)s were biocompatible as confirmed by cell viability tests, and may find applications in drug delivery, biosensing, biodetection, and nano-/micro-reactors.The Supporting Information is available free of charge on the ACS Publications website at DOI:… Materials and methods, experimental details, characterization data (PDF).Videos of vesicle disruption under the stimuli of H2O2 or light irradiation (AVI).

show abstract

“…Self-assembly MRI contrast reagent Antimicrobial nanoparticles [82,9] Tyrosine-NTA (Tyr-NTA) vii (60 °C, tetramethylene sulfone) - [9] Sar-NTA i, ii, iii Hydrophilic block Stealth property, antifouling [4] NEG-NTA i, iii, iv Omnisoluble in solvents Mechanism research [83,84] NBG-NTA i, ii, iii, iv Temperature responsiveness Hydrophobic block [85][86][87] NAG-NTA i Self-assembly Postmodification [88] MeSPG-NTA i Self-assembly Oxidation responsiveness Ref.…”

Section: Polymerization Of Ntasmentioning

confidence: 99%

An Inspection into Multifarious Ways to Synthesize Poly(Amino Acid)s

Zheng

Bai

Tao

et al. 2021

Macromol. Rapid Commun.

Self Cite

View full text Add to dashboard Cite

Poly(𝜶-amino acid)s (PAAs) attract growing attention due to their essential role in the application as biomaterials. To synthesize PAAs with desired structures and properties, scientists have developed various synthetic techniques with respective advantages. Here, different approaches to preparing PAAs are inspected. Basic features and recent progresses of these methods are summarized, including polymerizations of amino acid N-carboxyanhydrides (NCAs), amino acid N-thiocarboxyanhydrides (NTAs), and N-phenoxycarbonyl amino acids (NPCs), as well as other synthetic routes. NCA is the most classical monomer to prepare PAAs with high molecular weights (MWs). NTA polymerizations are promising alternative pathways to produce PAAs, which can tolerate nucleophiles including alcohols, mercaptans, carboxyl acids, and water. By various techniques including choosing appropriate solvents or using organic acids as promoters, NTAs polymerize to produce polypeptoids and polypeptides with narrow dispersities and designed MWs up to 55.0 and 57.0 kg mol −1 , respectively. NPC polymerizations are phosgene-free ways to synthesize polypeptides and polypeptoids. For the future prospects, detail investigations into polymerization mechanisms of NTA and NPC are expected. The synthesis of PAAs with designed topologies and assembly structures is another intriguing topic. The advantages and unsettled problems in various synthetic ways are discussed for readers to choose appropriate approaches for PAAs.

show abstract

Are N‐substituted glycine N‐thiocarboxyanhydride monomers really hard to polymerize?

Cited by 37 publications

References 40 publications

Solution Self-Assembly of Coil-Crystalline Diblock Copolypeptoids Bearing Alkyl Side Chains

Solution Self-Assembly of Coil-Crystalline Diblock Copolypeptoids Bearing Alkyl Side Chains

Oxidation-Sensitive Polymersomes Based on Amphiphilic Diblock Copolypeptoids

An Inspection into Multifarious Ways to Synthesize Poly(Amino Acid)s

Contact Info

Product

Resources

About