Comparison of Lipoic and Asparagusic Acid for Surface‐Initiated Disulfide‐Exchange Polymerization

Carmine, Alessio; Domoto, Yuya; Sakai, Naomi; Matile, Stefan

doi:10.1002/chem.201301567

Cited by 36 publications

(32 citation statements)

References 46 publications

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“…This finding confirmed previous observations [21] that the chemistry on surfaces,d ominated by powerful proximity effects in confined space,and chemistry in solution are not the same.F urther studies focused mostly on S1H3 because of these impressive EC 50 values.…”

Section: Entries 3-8)supporting

confidence: 91%

Complex Functional Systems with Three Different Types of Dynamic Covalent Bonds

Zhang

Matile

2015

Angewandte Chemie

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Multicomponent surface architectures are introduced that operate with three different dynamic covalent bonds.Disulfide exchange under basic conditions accounts for the growth of p stacks on solid surfaces.Hydrazone exchange under acidic conditions is used to add as econd coaxial string or stack, and boronic ester exchange under neutral conditions is used to co-align at hird one.T he newly introduced boronic ester exchange chemistry is compatible with stacka nd string exchange without interference from the orthogonal hydrazone and disulfide exchange.T he functional relevance of surface architectures with three different dynamic covalent bonds is exemplified with the detection of polyphenol natural products, such as epigallocatechin gallate,i nc ompetition experiments with alizarin red. These results describe synthetic strategies to create functional systems of unprecedented sophistication with regardtod ynamic covalent chemistry.

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Section: Entries 3-8)supporting

confidence: 91%

Complex Functional Systems with Three Different Types of Dynamic Covalent Bonds

Zhang

Matile

2015

Angewandte Chemie

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“…Accordingly, to extend the utility of sulfur‐containing macromolecules, polymers containing disulfide bonds have been synthesized. Due to the dynamic nature of the covalent disulfide bond, polydisulfides have been applied as adaptable, self‐sorting, and self‐healing materials . Furthermore, these polymers potentially are candidates for biomedical applications as polymeric gene or drug carrier systems by virtue of their inherent degradability under redox conditions (e.g., by glutathione).…”

Section: Chemistrymentioning

confidence: 99%

Sulfur Chemistry in Polymer and Materials Science

Mutlu

Ceper

et al. 2018

Macromol. Rapid Commun.

258

220

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The ORCID identification number(s) for the author(s) of this article can be found under https://doi.org/10.1002/marc.201800650. ChemistryBefore moving to the recent advances within the last 5 years in the diverse applications of sulfur chemistry in polymer and Sulfur-Containing PolymersSulfur and its functional groups are major players in an area of exciting research taking place in modern polymer and materials science, both in academia and industry. In fact, manifold sulfur-based reactions that are both exceptionally versatile as well as tremendously useful have been implemented, and further utilized for the design and preparation of polymeric materials that lead to a plethora of applications ranging from medicine to optics and nanotechnology to separation science. Hence, within this review, an overview of strategies and developments used over the last 5 years to reinforce the importance of the sulfur functional group in modern polymer and materials science is presented. In particular, many important references in the primary literature of sulfur chemistry are referred to, including thiol-ene, thiol-yne, thiol-Michael addition, disulfide cross-linking, and thiol-disulfide exchange, among others, by explaining and illustrating the important principles. Last but not least, the grand aim to underpin the importance of sulfur in modern polymer and materials science is achieved by presenting selected examples in diverse fields and postulating the respective potential for real-world applications. he is now a full professor at KIT.sulfur atoms, and tetraphenylethene-bearing di(alkyl bromide) (Scheme 3). The yield of the polymerization was dependent on the di(alkyl bromide) monomer; the longer spacer between the aromatic moiety and the reactive bromide end groups Scheme 1. The discussion henceforth focuses on the synthesis of polymers possessing the depicted sulfur functional groups. Scheme 2.Representative examples of polythioethers prepared via A) the nucleophilic substitution reaction between an electrophilic dihalide with nucleophilic derivatives of dithiols under alkaline conditions; B) the thiol-ene/yne addition reaction between AA and BB type monomers (i.e., dithiols and dienes/diynes); and C) radical or ionic ring-opening of sulfurcontaining strained rings.Scheme 3. The thiol-bromo polymerization of conformationally fixed monomers to provide multifunctional polymers. [19] Macromol. Rapid Commun. 2019, 40, 1800650 Scheme 4. The regioselective selective nucleophilic aromatic substitution between thiol and fluorinated aromatic compounds, the para-fluorothiol reaction (PFTR).Scheme 5. Synthesis of a linear polymer via PFTR-reaction. [21]

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“…Polymerization of cyclic cationic disulfides by thiol‐disulfide exchange is another method of synthesis of bioreducible polycations, which includes reactions directly involving sulfur. A prototypical example of such reaction is the ring opening polymerization of lipoic acid or similar cyclic disulfides like asparagusic acid . Historically, probably the first example of a bioreducible polycation prepared by this method has been described by Balakirev et al The authors prepared a cationic derivative of lipoic acid, which was polymerized by opening the 1,2‐dithiolane ring using a thiol‐containing peptide or a reducing agent dithiothreitol.…”

Section: Synthesis Of Bioreducible Polycationsmentioning

confidence: 99%

Bioreducible Polycations in Nucleic Acid Delivery: Past, Present, and Future Trends

Oupický

2014

Macromolecular Bioscience

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Polycations that are degradable by reduction of disulfide bonds are developed for applications in delivery of nucleic acids. This paper surveys methods of synthesis of bioreducible polycations and discusses current understanding of the mechanism of action of bioreducible polyplexes. Emphasis is placed on the relationship between the biological redox environment and toxicity, trafficking, transfection activity, and in vivo behavior of bioreducible polycations and polyplexes.

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Comparison of Lipoic and Asparagusic Acid for Surface‐Initiated Disulfide‐Exchange Polymerization

Cited by 36 publications

References 46 publications

Complex Functional Systems with Three Different Types of Dynamic Covalent Bonds

Complex Functional Systems with Three Different Types of Dynamic Covalent Bonds

Sulfur Chemistry in Polymer and Materials Science

Bioreducible Polycations in Nucleic Acid Delivery: Past, Present, and Future Trends

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