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Helmut Schlaad - One of the best experts on this subject based on the ideXlab platform.
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Synthesis of polysarcosine from air and moisture stable N-phenoxycarbonyl-N-methylglycine assisted by tertiary amine base
Polymer Chemistry, 2016Co-Authors: Afroditi Doriti, Sarah M. Brosnan, Steffen M. Weidner, Helmut SchlaadAbstract:Polysarcosine (Mn = 3650–20 000 g mol−1, Đ ∼ 1.1) was synthesized from the air and moisture stable N-phenoxycarbonyl-N-methylglycine. Polymerization was achieved by in situ transformation of the urethane precursor into the corresponding N-methylglycine-N-Carboxyanhydride, when in the presence of a non-nucleophilic tertiary amine base and a primary amine initiator.
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Primary ammonium/tertiary amine-mediated controlled ring opening polymerisation of amino acid N-Carboxyanhydrides.
Chemical communications (Cambridge England), 2015Co-Authors: Charlotte D Vacogne, Helmut SchlaadAbstract:Stable commercial primary ammonium chlorides were combined with tertiary amines to initiate the controlled ring opening polymerisation of amino acid N-Carboxyanhydrides to yield polypeptides with defined end group structure, predetermined molar mass and narrow molar mass distribution.
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primary ammonium tertiary amine mediated controlled ring opening polymerisation of amino acid n carboxyanhydrides
Chemical Communications, 2015Co-Authors: Charlotte D Vacogne, Helmut SchlaadAbstract:Stable commercial primary ammonium chlorides were combined with tertiary amines to initiate the controlled ring opening polymerisation of amino acid N-Carboxyanhydrides to yield polypeptides with defined end group structure, predetermined molar mass and narrow molar mass distribution.
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synthesis of nearly monodisperse polystyrene polypeptide block copolymers via polymerisation of n carboxyanhydrides
Chemical Communications, 2003Co-Authors: Ivaylo Dimitrov, Helmut SchlaadAbstract:Primary amine hydrochlorides promote a well-controlled ring-opening polymerisation of Z-L-lysine-N-Carboxyanhydride in DMF at 40–80 °C; the polystyrene–poly(Z-L-lysine) block copolymers synthesised exhibit a very narrow molecular weight distribution, close to a Poisson distribution.
Timothy J. Deming - One of the best experts on this subject based on the ideXlab platform.
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Controlled Synthesis of Phosphorylcholine Derivatives of Poly(serine) and Poly(homoserine)
Journal of the American Chemical Society, 2015Co-Authors: Ilya Yakovlev, Timothy J. DemingAbstract:We report methods for the synthesis of polypeptides that are fully functionalized with desirable phosphorylcholine, PC, groups. Because of the inherent challenges in the direct incorporation of the PC group into α-amino acid N-Carboxyanhydride (NCA) monomers, we developed a synthetic approach that combined functional NCA polymerization with efficient postpolymerization modification. While poly(l-phosphorylcholine serine) was found to be unstable upon synthesis, we successfully prepared poly(l-phosphorylcholine homoserine) with controlled chain lengths and found these to be water-soluble with disordered chain conformations.
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Soluble, Clickable Polypeptides from Azide-Containing N-Carboxyanhydride Monomers
ACS Macro Letters, 2013Co-Authors: Allison J. Rhodes, Timothy J. DemingAbstract:We report a method for the synthesis of soluble, well-defined, azide-functionalized polypeptides via living polymerization of new azide-containing amino acid N-Carboxyanhydride (NCA) monomers. Homo and diblock azidopolypeptides were prepared with controlled segment lengths using (PMe3)4Co initiator and were subsequently modified by reaction with functional alkyne reagents. The azide groups were found to be quantitatively converted to the corresponding triazole derivatives, and the functionalized polymers were obtained in high yield. This methodology provides a facile and straightforward method for preparation of functional and side-chain reactive, high molecular weight polypeptides.
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Ring-Opening Polymerization of Amino Acid N -Carboxyanhydrides
Polymer Science: A Comprehensive Reference, 2012Co-Authors: Timothy J. DemingAbstract:This chapter summarizes methods for the synthesis of polypeptides by ring-opening polymerization. Traditional and recently improved methods for polymerization of α-amino acid N -carboxyanhydrides (NCAs) are described. Use of these methods and strategies for the preparation of block and branched copolypeptides are also presented, as well as analysis of the synthetic scope of different approaches. Finally, strategies for obtaining highly functional polypeptides in pure form are detailed.
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Glycopolypeptides via living polymerization of glycosylated-L-lysine N-Carboxyanhydrides.
Journal of the American Chemical Society, 2010Co-Authors: Jessica R. Kramer, Timothy J. DemingAbstract:The preparation of new glycosylated-l-lysine-N-Carboxyanhydride (glyco-K NCA) monomers is described. These monomers employ C-linked sugars and amide linkages to lysine for improved stability without sacrificing biochemical properties. Three glyco-K NCAs were synthesized, purified, and found to undergo living polymerization using transition metal initiation. These are the first living polymerizations of glycosylated NCAs and were used to prepare well-defined, high molecular weight glycopolypeptides and block and statistical glycocopolypeptides. This methodology solves many long-standing problems in the direct synthesis of glycopolypeptides from N-Carboxyanhydrides relating to monomer synthesis, purification, and polymerization and gives polypeptides with 100% glycosylation. These long chain glycopolypeptides have potential to be good mimics of natural high molecular weight glycoproteins.
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Living polymerization of α-amino acid-N-Carboxyanhydrides
Journal of Polymer Science Part A: Polymer Chemistry, 2000Co-Authors: Timothy J. DemingAbstract:This article reviews recent developments in the polymerization of α-amino acid- N-Carboxyanhydrides (NCAs) to form polypeptides. Traditional methods used to polymerize these monomers are described, and limitations in the utility of these systems for the preparation of polypeptides with controlled molecular weights and narrow molecular weight distributions are discussed. The development of transition-metal-based initiators, which activate the monomers to form covalent active species, permits the formation of polypeptides via the living polymerization of NCAs. In these systems, polymer molecular weights are controlled by monomer-to-initiator stoichiometry, polydispersities are low, and block copolypeptides can be prepared. The scope and limitations of these initiators and their key features and mode of operation are described in detail in this highlight. © 2000 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 38: 3011–3018, 2000
Colin Bonduelle - One of the best experts on this subject based on the ideXlab platform.
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Amphiphilic Nucleobase-Containing Polypeptide Copolymers—Synthesis and Self-Assembly
Polymers, 2020Co-Authors: Michel Nguyen, Sébastien Lecommandoux, Khalid Ferji, Colin BonduelleAbstract:Nucleobase-containing polymers are an emerging class of building blocks for the self-assembly of nanoobjects with promising applications in nanomedicine and biology. Here we present a macromolecular engineering approach to design nucleobase-containing polypeptide polymers incorporating thymine that further self-assemble in nanomaterials. Diblock and triblock copolypeptide polymers were prepared using sequential ring-opening polymerization of γ-Benzyl-l-glutamate N-Carboxyanhydride (BLG-NCA) and γ-Propargyl-l-glutamate N-Carboxyanhydride (PLG-NCA), followed by an efficient copper(I)-catalyzed azide alkyne cycloaddition (CuAAc) functionalization with thymidine monophosphate. Resulting amphiphilic copolymers were able to spontaneously form nanoobjects in aqueous solutions avoiding a pre-solubilization step with an organic solvent. Upon self-assembly, light scattering measurements and transmission electron microscopy (TEM) revealed the impact of the architecture (diblock versus triblock) on the morphology of the resulted nanoassemblies. Interestingly, the nucleobase-containing nanoobjects displayed free thymine units in the shell that were found available for further DNA-binding.
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Aqueous Ring-Opening Polymerization-Induced Self-Assembly (ROPISA) of N-Carboxyanhydrides
Angewandte Chemie International Edition, 2020Co-Authors: Chloé Grazon, Sébastien Lecommandoux, Pedro Salas-ambrosio, Emmanuel Ibarboure, Alix Buol, Elisabeth Garanger, Mark Grinstaff, Colin BonduelleAbstract:We report the first aqueous ring‐opening polymerization (ROP) of N‐carboxyanhydrides (NCA) using α‐amino‐poly(ethylene oxide) macroinitiator to protect NCA monomers from hydrolysis through spontaneous in situ self‐assembly (ISA). This ROPISA process affords well‐defined amphiphilic diblock copolymers that simultaneously form original needle‐like nano‐objects.
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aqueous ring opening polymerization induced self assembly ropisa of n carboxyanhydrides
Angewandte Chemie, 2020Co-Authors: Chloé Grazon, Sébastien Lecommandoux, Emmanuel Ibarboure, Alix Buol, Elisabeth Garanger, Mark Grinstaff, Pedro Salasambrosio, Colin BonduelleAbstract:Reported here is the first aqueous ring-opening polymerization (ROP) of N-Carboxyanhydrides (NCAs) using α-amino-poly(ethylene oxide) as a macroinitiator to protect the NCA monomers from hydrolysis through spontaneous in situ self-assembly (ISA). This ROPISA process affords well-defined amphiphilic diblock copolymers that simultaneously form original needle-like nanoparticles.
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Aqueous Ring‐Opening Polymerization Induced Self‐Assembly (ROPISA) of N‐carboxyanhydrides
Angewandte Chemie (International ed. in English), 2019Co-Authors: Chloé Grazon, Sébastien Lecommandoux, Emmanuel Ibarboure, Alix Buol, Elisabeth Garanger, Mark Grinstaff, Pedro Salas‐ambrosio, Colin BonduelleAbstract:Reported here is the first aqueous ring-opening polymerization (ROP) of N-Carboxyanhydrides (NCAs) using α-amino-poly(ethylene oxide) as a macroinitiator to protect the NCA monomers from hydrolysis through spontaneous in situ self-assembly (ISA). This ROPISA process affords well-defined amphiphilic diblock copolymers that simultaneously form original needle-like nanoparticles.
Sébastien Lecommandoux - One of the best experts on this subject based on the ideXlab platform.
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Amphiphilic Nucleobase-Containing Polypeptide Copolymers—Synthesis and Self-Assembly
Polymers, 2020Co-Authors: Michel Nguyen, Sébastien Lecommandoux, Khalid Ferji, Colin BonduelleAbstract:Nucleobase-containing polymers are an emerging class of building blocks for the self-assembly of nanoobjects with promising applications in nanomedicine and biology. Here we present a macromolecular engineering approach to design nucleobase-containing polypeptide polymers incorporating thymine that further self-assemble in nanomaterials. Diblock and triblock copolypeptide polymers were prepared using sequential ring-opening polymerization of γ-Benzyl-l-glutamate N-Carboxyanhydride (BLG-NCA) and γ-Propargyl-l-glutamate N-Carboxyanhydride (PLG-NCA), followed by an efficient copper(I)-catalyzed azide alkyne cycloaddition (CuAAc) functionalization with thymidine monophosphate. Resulting amphiphilic copolymers were able to spontaneously form nanoobjects in aqueous solutions avoiding a pre-solubilization step with an organic solvent. Upon self-assembly, light scattering measurements and transmission electron microscopy (TEM) revealed the impact of the architecture (diblock versus triblock) on the morphology of the resulted nanoassemblies. Interestingly, the nucleobase-containing nanoobjects displayed free thymine units in the shell that were found available for further DNA-binding.
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Aqueous Ring-Opening Polymerization-Induced Self-Assembly (ROPISA) of N-Carboxyanhydrides
Angewandte Chemie International Edition, 2020Co-Authors: Chloé Grazon, Sébastien Lecommandoux, Pedro Salas-ambrosio, Emmanuel Ibarboure, Alix Buol, Elisabeth Garanger, Mark Grinstaff, Colin BonduelleAbstract:We report the first aqueous ring‐opening polymerization (ROP) of N‐carboxyanhydrides (NCA) using α‐amino‐poly(ethylene oxide) macroinitiator to protect NCA monomers from hydrolysis through spontaneous in situ self‐assembly (ISA). This ROPISA process affords well‐defined amphiphilic diblock copolymers that simultaneously form original needle‐like nano‐objects.
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aqueous ring opening polymerization induced self assembly ropisa of n carboxyanhydrides
Angewandte Chemie, 2020Co-Authors: Chloé Grazon, Sébastien Lecommandoux, Emmanuel Ibarboure, Alix Buol, Elisabeth Garanger, Mark Grinstaff, Pedro Salasambrosio, Colin BonduelleAbstract:Reported here is the first aqueous ring-opening polymerization (ROP) of N-Carboxyanhydrides (NCAs) using α-amino-poly(ethylene oxide) as a macroinitiator to protect the NCA monomers from hydrolysis through spontaneous in situ self-assembly (ISA). This ROPISA process affords well-defined amphiphilic diblock copolymers that simultaneously form original needle-like nanoparticles.
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Aqueous Ring‐Opening Polymerization Induced Self‐Assembly (ROPISA) of N‐carboxyanhydrides
Angewandte Chemie (International ed. in English), 2019Co-Authors: Chloé Grazon, Sébastien Lecommandoux, Emmanuel Ibarboure, Alix Buol, Elisabeth Garanger, Mark Grinstaff, Pedro Salas‐ambrosio, Colin BonduelleAbstract:Reported here is the first aqueous ring-opening polymerization (ROP) of N-Carboxyanhydrides (NCAs) using α-amino-poly(ethylene oxide) as a macroinitiator to protect the NCA monomers from hydrolysis through spontaneous in situ self-assembly (ISA). This ROPISA process affords well-defined amphiphilic diblock copolymers that simultaneously form original needle-like nanoparticles.
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Polypeptide Nanoparticles Obtained from Emulsion Polymerization of Amino Acid N-Carboxyanhydrides
Journal of the American Chemical Society, 2019Co-Authors: Jaco Jacobs, Sébastien Lecommandoux, Emmanuel Ibarboure, Dražen Pavlović, Hannah Prydderch, Mohammad-amin Moradi, Johan Heuts, Andreas HeiseAbstract:Polypeptide nanoparticles were obtained by the miniemulsion polymerization of S-(o-nitrobenzyl)-l-cysteine (NBC) N-Carboxyanhydride (NCA). Through process optimization, reaction conditions were identified that allowed the polymerization of the water sensitive NCA to yield nanoparticles of about 220 nm size. Subsequent UV-irradiation of the nanoparticle emulsions caused the in situ removal of the nitrobenzyl group and particle cross-linking through disulfide bond formation accompanied by the shrinkage of the particles.
Charlotte D Vacogne - One of the best experts on this subject based on the ideXlab platform.
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Primary ammonium/tertiary amine-mediated controlled ring opening polymerisation of amino acid N-Carboxyanhydrides.
Chemical communications (Cambridge England), 2015Co-Authors: Charlotte D Vacogne, Helmut SchlaadAbstract:Stable commercial primary ammonium chlorides were combined with tertiary amines to initiate the controlled ring opening polymerisation of amino acid N-Carboxyanhydrides to yield polypeptides with defined end group structure, predetermined molar mass and narrow molar mass distribution.
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primary ammonium tertiary amine mediated controlled ring opening polymerisation of amino acid n carboxyanhydrides
Chemical Communications, 2015Co-Authors: Charlotte D Vacogne, Helmut SchlaadAbstract:Stable commercial primary ammonium chlorides were combined with tertiary amines to initiate the controlled ring opening polymerisation of amino acid N-Carboxyanhydrides to yield polypeptides with defined end group structure, predetermined molar mass and narrow molar mass distribution.
