Orthogonal Click Postfunctionalization of Alternating Copolymers Prepared by Nitroxide‐Mediated Polymerization

Tesch, Matthias; Kudruk, Sergej; Letzel, Matthias C.; Studer, Armido

doi:10.1002/chem.201605639

Cited by 15 publications

(3 citation statements)

References 81 publications

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“…The dihydrotetrazine 17 was prepared from ethyl diazoacetate ( 5 ) . Breaking the symmetry of dihydrotetrazine 17 succeeded via base-promoted transesterification using azidopropanol to furnish 18 in good yield. The addition of molecular sieves turned out to be essential in terms of scavenging developing methanol.…”

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confidence: 99%

Copper-Free Click Reaction Sequence: A Chemoselective Layer-by-Layer Approach

Meinecke

Koert

2019

Org. Lett.

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An additive-free chemoselective ligation of dual clickable building blocks is demonstrated. The challenge of balancing reactivity and stability was achieved by employing a small, electron-deficient tetrazine bearing an azido group and an enol ether functionalized cyclooctyne. The chemoselective sequence of strain-promoted azide−alkyne cycloaddition (SPAAC) and inverse-electron-demand Diels−Alder (IEDDA) reaction is demonstrated with a cholic acid derived triazide as a molecular surface model for layer-by-layer synthesis.

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confidence: 99%

Copper-Free Click Reaction Sequence: A Chemoselective Layer-by-Layer Approach

Meinecke

Koert

2019

Org. Lett.

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“…Before the reaction, 1:1 (v/v) H 2 O/ t BuOH, DMF, and H 2 O were degassed by means of freeze–pump–thaw cycles, and all processes were conducted under Ar. To perform the reaction, the following stock solutions were prepared: (1) diazidopeptide 14 or 15 in H 2 O/ t BuOH (1/1, v/v), (2) dialkyne linker 16 or 17 in H 2 O/ t BuOH (1/1, v/v) or DMF, (3) CuSO 4 ·5H 2 O in H 2 O, (4) tris(3-hydroxypropyltriazolylmethyl)amine (THPTA) , in H 2 O, and (5) sodium ascorbate in H 2 O. A stock solution of the dialkyne linker (1.0–1.1 equiv) was added dropwise to the stock solution of diazidopeptide (1.0 equiv).…”

Section: Methodsmentioning

confidence: 99%

Structure-Based Identification of Potent Lysine-Specific Demethylase 1 Inhibitor Peptides and Temporary Cyclization to Enhance Proteolytic Stability and Cell Growth-Inhibitory Activity

et al. 2021

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Peptides are attractive drug candidates, but their utility is greatly limited by their inherent susceptibility to proteolytic degradation and their inability to pass through the cell membrane. Here, we employ a strategy of temporary cyclization to develop a cell-active lysine-specific demethylase 1 (LSD1/KDM1A) inhibitor peptide. We first identified a highly potent LSD1-inhibitory linear peptide, with the assistance of X-ray crystal structure data of inhibitor peptide-bound LSD1·CoREST. The peptide was converted to a redox-activatable cyclic peptide incorporating cell-penetrating peptide (CPP), expecting selective activation under intracellular reducing conditions. The cyclic peptide moiety exhibited enhanced stability to protease and was converted to the linear, unmodified LSD1 inhibitor peptide under reducing conditions. The cyclic peptide with CPP inhibited the proliferation of human acute myeloid leukemia cells (HL-60) in the low micromolar concentration range.

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“…Then, the alternating radical copolymerization of VAc with MAF-TBE was also reported using MAMA-SG1-mediated NMP (Scheme 8). 40 Tesch et al 41 prepared a novel alternating copolymer based on 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) and [(6trimethylsilyl)-hex-5-yn-1-yl]vinyl ether (THVE) via NMP. In 2020, Peltekoff et al 42 produced poly(pentafluorostyrene-ranmethyl methacrylate) copolymers via NMP to develop original dielectric polymers.…”

Section: Synthesis Via Reversible Deactivation Radical Polymerization...mentioning

confidence: 99%

Well-Defined Fluorinated Copolymers: Current Status and Future Perspectives

et al. 2021

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Well-defined fluoropolymers exhibit unique properties such as excellent oil and water repellency, satisfactory thermal stability, low refractive index, and low surface energy.The origin of these properties is attributed to the presence of strong electronegative and low polarizable Fluorine atom in the backbone of such polymers which leads to a strong C F bond (with a high bond dissociation energy of 485 kJ mol −1 ). Due to these features, these polymers have found applications as functional coatings, thermoplastics, biomedical items, separators and binders for Li-ion batteries, fuel cell membranes, piezoelectric devices, high quality wires and cables, etc. Usually, fluoropolymers are synthesized by conventional radical (co)polymerization of fluoroalkenes which leads to the production of (co)polymers with ill-defined end group, uncontrolled molar mass, and high dispersity values. In the last two decades, significant developments of various reversible deactivation radical polymerization (RDRP) techniques have helped the design of macromolecular architectures (including block, graft, star, dendrimers) on demand. However, for relevant new applications, well-defined fluoropolymers with well-defined macromolecular architectures (e.g. block copolymers as thermoplastic elastomers and electroactive polymers or graft copolymers for fuel cell membranes) are required.Several RDRP methods developed in the last couple of decades have paved the way for the synthesis of (co)polymers with well-defined molar mass, dispersity, chain end-functionality and

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Orthogonal Click Postfunctionalization of Alternating Copolymers Prepared by Nitroxide‐Mediated Polymerization

Cited by 15 publications

References 81 publications

Copper-Free Click Reaction Sequence: A Chemoselective Layer-by-Layer Approach

Copper-Free Click Reaction Sequence: A Chemoselective Layer-by-Layer Approach

Structure-Based Identification of Potent Lysine-Specific Demethylase 1 Inhibitor Peptides and Temporary Cyclization to Enhance Proteolytic Stability and Cell Growth-Inhibitory Activity

Well-Defined Fluorinated Copolymers: Current Status and Future Perspectives

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