Dual pH and temperature responsive helical copolymer libraries with pendant chiral leucine moieties

Bauri, Kamal; Pant, Shashank; Roy, Saswati Ghosh; De, Priyadarsi

doi:10.1039/c3py00434a

Cited by 62 publications

(58 citation statements)

References 62 publications

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“…26 The amino acid based vinyl monomer Boc-Leu-HEMA was synthesized by coupling reaction of Boc-L-Leu-OH with HEMA in the presence of DCC and DMAP following the previously reported procedure. 27 Solvents such as hexanes, acetone, diethyl ether, tetrahydrofuran (THF), methanol (MeOH), dimethyl sulfoxide (DMSO), etc. were purified by standard procedures.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of amino acid based covalently cross-linked polymeric gels using tetrakis(hydroxymethyl) phosphonium chloride as a cross-linker

Vaish

Roy

2015

Polymer

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Section: Methodsmentioning

confidence: 99%

Synthesis of amino acid based covalently cross-linked polymeric gels using tetrakis(hydroxymethyl) phosphonium chloride as a cross-linker

Vaish

Roy

2015

Polymer

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“…The previously mentioned processes are commonly known as the temperature directed morphology transformation (TDMT) or the polymerizationinduced thermal self-assembly (PITSA). [60][61][62][63] So the coating of chiral materials on different nanostructures generates a single entity which will combine the intriguing properties of both chiral materials and nanostructures. 22 Supramolecularly self-assembled nanostructures covered with bioactive building blocks have been actively explored as promising materials in the field of biotechnology.…”

Section: Introductionmentioning

confidence: 99%

Polymerization-induced self-assembly driving chiral nanostructured materials

et al. 2015

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To prepare chiral nanostructures coated with bioactive molecules, a side-chain amino acid containing macromolecular chain transfer agent (macroCTA), poly(Boc-L-alanine methacryloyloxyethyl ester) (PBLAEMA), has been used as the steric stabilizer for the reversible addition-fragmentation chain transfer (RAFT) mediated dispersion polymerization of benzyl methacrylate (BzMA) in methanol at 65°C. Gel permeation chromatography (GPC) analysis confirmed an efficient and well-controlled block copolymerization. A full spectrum of morphologies spanning spherical micelles, worm like micelles, fibres and vesicles could be attained by tuning (i) the length of the solvophobic block and (ii) the total solid content at which the block copolymerization is performed. Interestingly, a purely fibre phase morphology formed a thermoresponsive gel at room temperature above a critical fibre entanglement concentration, which underwent degelation upon heating because of the morphological transformation from anisotropic fibre to isotropic sphere. In actual fact, twisted nano-fibres have been formed through the hierarchical selfassembling of polymerization induced self-assembly (PISA) generated macromolecules in the gel state.Circular dichroism (CD) spectroscopy was used to elucidate chiroptical properties. Additionally, a high demanding wrinkle surface has been constructed preliminarily from this copolymer dispersion solution.Successful Boc-group expulsion facilitates the disassembly of vesicles to either worms or spheres with an appreciable cationic character below pH 7.0 as revealed by aqueous electrophoresis studies. Though the creation of nano-objects through PISA is well-known, fabricating chiral nanostructures with reactive handles and their hierarchical self-organization to have functional architectures is a less explored area. In this present work we were able to hybridize PISA, chirality and hierarchical self-assembling. † Electronic supplementary information (ESI) available: GPC chromatograms, CD spectra, 1 H NMR spectrum and DLS size distributions of various block copolymers. See

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“…Hydrophobic amino acid side chains, such as those of leucine and isoleucine, have been used to add LCST behaviour to polymers. [49,50] Coupling isopropyl amine to an aspartic acid monomer has also achieved an LCST response. [12] Recently, many zwitterionic amino acid functional polymers have been synthesized; however, their UCST response is rarely reported.…”

Section: Temperature Responsementioning

confidence: 99%

Amino Acid Functional Polymers: Biomimetic Polymer Design Enabling Catalysis, Chiral Materials, and Drug Delivery

2016

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Amino acids are the natural building blocks for the world around us. Highly functional, these small molecules have unique catalytic properties, chirality, and biocompatibility. Imparting these properties to surfaces and other macromolecules is highly sought after and represents a fast-growing field. Polymers functionalized with amino acids in the side chains have tunable optical properties, pH responsiveness, biocompatibility, structure and self-assembly properties. Herein, we review the synthesis of amino acid functional polymers, discuss manipulation of available strategies to achieve the desired responsive materials, and summarize some exciting applications in catalysis, chiral particles, and drug delivery.

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Dual pH and temperature responsive helical copolymer libraries with pendant chiral leucine moieties

Cited by 62 publications

References 62 publications

Synthesis of amino acid based covalently cross-linked polymeric gels using tetrakis(hydroxymethyl) phosphonium chloride as a cross-linker

Synthesis of amino acid based covalently cross-linked polymeric gels using tetrakis(hydroxymethyl) phosphonium chloride as a cross-linker

Polymerization-induced self-assembly driving chiral nanostructured materials

Amino Acid Functional Polymers: Biomimetic Polymer Design Enabling Catalysis, Chiral Materials, and Drug Delivery

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