Synthesis and chiro-optical properties of copolymers from N-Boc-O-methacryloyl-(S)-serine benzhydryl ester and methyl methacrylate

Bush, Stephen M.; North, Michael; Sellarajah, Shane

doi:10.1016/s0032-3861(97)10004-0

Cited by 18 publications

(8 citation statements)

References 27 publications

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“…[20][21][22][23][24][25][26][27][28][29] North et al prepared various methacrylates based on serine and serine dior tripeptides. [30][31][32][33] Controlled polymerization techniques have also been used in this context. 34,35 For example, ring-opening metathesis polymerization (ROMP) was successfully employed to prepare a range of amino acid-functionalized homopolymers and block copolymers.…”

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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Section: Introductionmentioning

confidence: 99%

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

et al. 2015

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“…Thus, Endo and co-workers reported the polymer maintained a linear backbone structure with α-helix-shaped branches. Similar work by North et al involved the synthesis of a variety of serine-based amino acid branched polymers by radical polymerization, which differ from those of Endo and co-workers since the amino acid functionality is attached to the acrylate through the alcohol of the serine side chain . In addition, monomers bearing dipeptides and tripeptides attached through the acid and amine of the serine unit, respectively, were prepared …”

Section: Introductionmentioning

confidence: 99%

Amino Acid and Dipeptide Functionalized Polyolefins

Hopkins

Wagener

2003

Macromolecules

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N-protected amino acid and dipeptide branched, chiral polyolefins have been prepared using acyclic diene metathesis polycondensation chemistry. The polymerizations were performed in THF using Grubbs' second-generation catalyst. The polymers bearing CBz-protected amino acids and dipeptides are semicrystalline with melt transitions of up to 150 °C, whereas the polymers bearing BOC-protected amino acids and dipeptides are primarily amorphous with the exception of the di-BOC-protected lysine polymer, which is semicrystalline.

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“…[3] Polymerization of a serine-bearing monomer with acid-labile protecting groups on both the amine and carboxylic acid functionality, yielded a polymer that could be easily deprotected (10b). [134] The copolymerization with methyl methacrylate showed a nonlinear increase in optical activity, with up to 35 % chiral monomer incorporation, followed by a decrease in optical activity down to a negative rotation at 70 % chiral monomer incorporation. The optical activity of a model compound was negative as well, which suggests the positive optical rotation observed was due to asymmetric induction along the backbone of the polymer, and the negative optical activity observed was due to the presence of the serine unit.…”

Section: Chiral Polyolefins Bearing Branched Amino Acidsmentioning

confidence: 96%