Synthesis and Self-Assembly of Amphiphilic Chiral Poly(amino acid) Star Polymers

Skey, Jared; Willcock, Helen; Lammens, Mieke; Prez, Filip Du; O’Reilly, Rachel K.

doi:10.1021/ma101019g

Cited by 49 publications

(45 citation statements)

References 57 publications

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“…15. [203,587] 357 [357] 358 [582] 356 [239] 353 [222] 352 [222] 354 [236] 355 [427] 359 [170] 360 [533] 368 [292] 366 [486] 367 [423] 369 [58] 370 [383] 371 [245,246] 372 [464] AMPS Ϫ ϩ ϩ Ϫ ϩ ϩ Ϫ 363 [245,246] 361 [328] 362 [328] 364 [289] 365 [383] Ϫ Fig. 8.…”

Section: Monomers With Reactive Functionalitymentioning

confidence: 99%

Living Radical Polymerization by the RAFT Process – A Third Update

2012

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This paper provides a third update to the review of reversible deactivation radical polymerization (RDRP) achieved with thiocarbonylthio compounds (ZC(¼S)SR) by a mechanism of reversible addition-fragmentation chain transfer ( Chem. 2009Chem. , 62, 1402. This review cites over 700 publications that appeared during the period mid 2009 to early 2012 covering various aspects of RAFT polymerization which include reagent synthesis and properties, kinetics and mechanism of polymerization, novel polymer syntheses, and a diverse range of applications. This period has witnessed further significant developments, particularly in the areas of novel RAFT agents, techniques for end-group transformation, the production of micro/nanoparticles and modified surfaces, and biopolymer conjugates both for therapeutic and diagnostic applications.

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Section: Monomers With Reactive Functionalitymentioning

confidence: 99%

Living Radical Polymerization by the RAFT Process – A Third Update

2012

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“…We have recently reported that the phenylalanine methyl ester amino acid polymer can be utilized as a substrate for chiral enhancement due to the increased interaction between opposite enantiomers. (34) In this work we wanted to explore this interaction further using our new water soluble phenylalanine polymer (PAP). We proposed that at low pH when the PAP block is hydrophobic, there should be a stronger interaction with the opposite enantiomer compared to at high pH when the polymer is hydrophilic.…”

Section: Scheme 1 Synthesis Of Amphiphilic Diblock 2 Using Raft Polymmentioning

confidence: 99%

pH-Responsive Chiral Nanostructures

Willcock

Ieong

et al. 2011

Aust. J. Chem.

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There is great current interest in the design of robust synthetic polymers for the preparation of novel functional, well-defined, biocompatible and tailorable materials for a range of applications. In this work we have used reversible addition fragmentation chain transfer (RAFT) polymerization to prepare chiral and responsive amphiphilic block copolymers (based on polyphenylalanine acrylamide) which can be assembled at different pHs to form well-defined nanostructures, whose morphology and size were explored using TEM, DLS and SLS measurements and stability by fluorescence and NMR spectroscopy. 2The application of these chiral and responsive nanostructures in the resolution of hydrophilic racemic amino acids has also been explored.

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“…54,55 Amphiphilic star block copolymers containing phenylalanine methyl esters were synthesized and their potential use in enantiomer separation was investigated. 56 Block copolymers comprising poly(acrylic acid) and poly(N-acryloyl-(L)-phenylalanine), as well as the L-and D-leucine analogs, were used to prepare shell cross-linked micelles. 57,58 Finally, the same team developed several strategies to prepare polymeric nanoreactors based on a L-proline-based monomer; such nanoreactors were shown to efficiently catalyze aldol reactions.…”

Section: Introductionmentioning

confidence: 99%

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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Synthesis and Self-Assembly of Amphiphilic Chiral Poly(amino acid) Star Polymers

Cited by 49 publications

References 57 publications

Living Radical Polymerization by the RAFT Process – A Third Update

Living Radical Polymerization by the RAFT Process – A Third Update

pH-Responsive Chiral Nanostructures

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

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