Synthesis and reactions of cysteine-based telechelic polymers

Kudo, Hiroto; Sanda, Fumio; Endo, Takeshi

doi:10.1002/1099-0518(20010101)39:1<23::aid-pola30>3.0.co;2-4

Cited by 3 publications

(3 citation statements)

References 22 publications

(6 reference statements)

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“…80 However, in principle this functional group offers facile post-polymerization functionalization of polymers via thiol-ene and thiol-yne chemistries. This approach was recently exploited to functionalize polybutadiene, 81 and also to prepare new polyphosphoester-based micelles.…”

Section: 79mentioning

confidence: 99%

“…78,79 Amongst the various amino acids, cysteine has been only seldom used for the side chain functionalization of polymers, presumably because its thiol group impairs radical polymerization unless masked. 80 However, in principle this functional group offers facile post-polymerization functionalization of polymers via thiol-ene and thiol-yne chemistries. This approach was recently exploited to functionalize polybutadiene, 81 and also to prepare new polyphosphoester-based micelles.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterization of poly(amino acid methacrylate)-stabilized diblock copolymer nano-objects

et al. 2015

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International audienceAmino acids constitute one of Nature's most important building blocks. Their remarkably diverse properties (hydrophobic/hydrophilic character, charge density, chirality, reversible cross-linking etc.) dictate the structure and function of proteins. The synthesis of artificial peptides and proteins comprising main chain amino acids is of particular importance for nanomedicine. However, synthetic polymers bearing amino acid side-chains are more readily prepared and may offer desirable properties for various biomedical applications. Herein we describe an efficient route for the synthesis of poly(amino acid methacrylate)-stabilized diblock copolymer nano-objects. First, either cysteine or glutathione is reacted with a commercially available methacrylate-acrylate adduct to produce the corresponding amino acid-based methacrylic monomer (CysMA or GSHMA). Well-defined water-soluble macromolecular chain transfer agents (PCysMA or PGSHMA macro-CTAs) are then prepared via RAFT polymerization, which are then chain-extended via aqueous RAFT dispersion polymerization of 2-hydroxypropyl methacrylate. In situ polymerization- induced self-assembly (PISA) occurs to produce sterically-stabilized diblock copolymer nano-objects. Although only spherical nanoparticles could be obtained when PGSHMA was used as the sole macro-CTA, either spheres, worms or vesicles can be prepared using either PCysMA macro-CTA alone or binary mixtures of poly(glycerol monomethacrylate) (PGMA) with either PCysMA or PGSHMA macro-CTAs. The worms formed soft free-standing thermo-responsive gels that undergo degelation on cooling as a result of a worm-to-sphere transition. Aqueous electrophoresis studies indicate that all three copolymer morphologies exhibit cationic character below pH 3.5 and anionic character above pH 3.5. This pH sensitivity corresponds to the known behavior of the poly(amino acid methacrylate) steric stabilizer chains

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Section: 79mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of poly(amino acid methacrylate)-stabilized diblock copolymer nano-objects

et al. 2015

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“…Poly(sulfinyl acrylate)s exhibit some biological activity (366,367). Membranes bearing sulfoxide moieties are permeable, particularly to polar compounds (368)(369)(370). Aliphatic polysulfoxides having sulfoxide groups in the main chain can be used as novel polymeric oxidizing reagents, compatibilizers, and polymer solvents.…”

Section: Polysulfoxidesmentioning

confidence: 99%

Sulfur‐Containing Polymers

Kultys

2010

Encyclopedia of Polymer Science and Technology

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Sulfur-containing polymers, when considering their structure, make up a complex group of macromolecular compounds of varied and often remarkable features that determine their versatile applications.The presence of sulfur atoms in polymer structure, depending on the kind of functional group, can improve some important properties, such as mechanical, electrical, and optical, and then adhesion to metals, resistance to heat, chemicals, radiation, and bacteria, biocompatibility, and so on. These are their more important functional groups: sulfide -S-, polysulfide -S n -, sulfonyl -SO 2 -, sulfinyl -SO-, sulfo -SO 3 H, as well as some organic groups containing sulfur atoms, such as thioester -Sulfur-containing polymers can be used as high performance engineering plastics, chemically stable ion-exchange membranes in electromembrane processes, proton-conducting electrolytes, as well as optical, optoelectronic, and photochemical materials. Some polymers are employed in biomedical applications, for example, sulfopolymers as biomembranes and blood-compatible materials, and polysulfates and polysulfonates as antithrombotic or antiviral agents. The presence of sulfur, particularly in the form of disulfide bridges, plays an important role in biopolymers.The purpose of this review is mainly to present recent advances in the area of sulfur-containing polymers that may not yet have commercial applications. Nevertheless, older but still significant material has been included at the beginning of the discussion of each class. Poly(monosulfide)sPolymers containing a monosulfide linkage in both the main chain and the pendent group are the subject of many detailed studies. A few reviews of the synthesis and properties of all types of polymers have been published (1-4); like the one covering polymer with sulfur in the main chain that appeared in 1992 (3). Polysulfides with controlled and well-defined structures can be easily prepared. Nevertheless, the only commercial poly(monosulfide) is Ryton [Philips Petroleum Co., poly(thio-1,4-phenylene) more frequently referred to as poly(p-phenylene sulfide) or poly(phenylene sulfide) (PPS)].

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Synthesis and property of novel amino acid‐based polymers by self‐polyaddition of monomers containing both oxetanyl and carboxyl groups

Kudo

Ohshiro

Atsumi

et al. 2011

J. Polym. Sci. A Polym. Chem.

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A new synthetic strategy for polymers containing amino acids in the main chain was developed. Monomers N-oxetanylalanine (N-Oxe-Ala-COOH), N-oxetanylglutamic acid (N-Oxe-Glu-COOH), and N-oxetanyllysine (N-Oxe-Lys-COOH) containing both oxetanyl and carboxyl groups were synthesized, and self-polyaddition and self-copolyaddition of these monomers afforded the corresponding polymers containing amino acids in the main chain [poly( Ox Ala), poly( Ox Lys), poly ( Ox Glu), poly( Ox Ala-co-Ox Glu), poly( Ox Glu-co-Ox Lys), and poly ( Ox Ala-co-Ox Lys)] with molecular weight in the range of 920-6620, in satisfactory yields. The physical properties, such as solubility, glass transition temperature, and thermal stability, were consistent with the amount of carboxyl groups at the chain ends. Biodegradability of the polymers was examined by the biochemical oxygen demand method; the decomposition ratios of poly( Ox Ala) and poly( Ox Ala-co-Ox Glu) were about 60%, whereas that of poly( Ox Glu) was nearly 100% after 28 days.

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Synthesis and reactions of cysteine-based telechelic polymers

Cited by 3 publications

References 22 publications

Synthesis and characterization of poly(amino acid methacrylate)-stabilized diblock copolymer nano-objects

Synthesis and characterization of poly(amino acid methacrylate)-stabilized diblock copolymer nano-objects

Sulfur‐Containing Polymers

Synthesis and property of novel amino acid‐based polymers by self‐polyaddition of monomers containing both oxetanyl and carboxyl groups

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