- Click-Functionalization of a Poly(Tetrazine-co-Fluorene)-Conjugated Polymer with a Series of trans-Cyclooctene Derivatives
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A soluble poly(tetrazine) polymer was prepared via Suzuki polycondensation of 3,6-bis(5-bromofuran-2-yl)-1,2,4,5-tetrazine and a fluorene diboronate derivative. It can undergo efficient and quantitative post-polymerization inverse-electron-demand Diels–Al
- Kardelis, Vladimir,Denk, Maria M.,Adronov, Alex
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Read Online
- A far-red hybrid voltage indicator enabled by bioorthogonal engineering of rhodopsin on live neurons
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Membrane potential is a key aspect of cellular signalling and is dynamically regulated by an array of ion-selective pumps and channels. Fluorescent voltage indicators enable non-invasive optical recording of the cellular membrane potential with high spati
- Chen, Peng R.,Lin, Chang,Liu, Shuzhang,Luo, Huixin,Peng, Luxin,Xu, Yongxian,Zeng, Xiangmei,Zheng, Huangtao,Zou, Peng
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- Fluorescent prodrug for specific marker tumor cells as well as preparation method and application thereof
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The fluorescent prodrug is characterized in that the fluorescent prodrug comprises a compound represented by the formula (I) and/or a compound represented by the formula (II). The preparation method comprises the following steps: carrying out light-shield
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Paragraph 0050; 0056
(2021/09/01)
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- A Bioorthogonal Click Chemistry Toolbox for Targeted Synthesis of Branched and Well-Defined Protein–Protein Conjugates
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Bioorthogonal chemistry holds great potential to generate difficult-to-access protein–protein conjugate architectures. Current applications are hampered by challenging protein expression systems, slow conjugation chemistry, use of undesirable catalysts, or often do not result in quantitative product formation. Here we present a highly efficient technology for protein functionalization with commonly used bioorthogonal motifs for Diels–Alder cycloaddition with inverse electron demand (DAinv). With the aim of precisely generating branched protein chimeras, we systematically assessed the reactivity, stability and side product formation of various bioorthogonal chemistries directly at the protein level. We demonstrate the efficiency and versatility of our conjugation platform using different functional proteins and the therapeutic antibody trastuzumab. This technology enables fast and routine access to tailored and hitherto inaccessible protein chimeras useful for a variety of scientific disciplines. We expect our work to substantially enhance antibody applications such as immunodetection and protein toxin-based targeted cancer therapies.
- Baalmann, Mathis,Bitsch, Sebastian,Deweid, Lukas,Ilkenhans, Nadja,Kolmar, Harald,Neises, Laura,Schneider, Hendrik,Werther, Philipp,Wilhelm, Jonas,Wolfring, Martin,Wombacher, Richard,Ziegler, Michael J.
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supporting information
p. 12885 - 12893
(2020/06/02)
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- Paclitaxel prodrug, preparation method and application thereof
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The invention provides a paclitaxel prodrug, a preparation method and application thereof. Compared with a chemotherapeutic drug paclitaxel (PTX), the paclitaxel prodrug (TCO-PTX) provided by the invention has the advantages that a drug active site of pac
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Paragraph 0061; 0066
(2020/09/23)
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- Synthesis of Functionalized N-Acetyl Muramic Acids to Probe Bacterial Cell Wall Recycling and Biosynthesis
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Uridine diphosphate N-acetyl muramic acid (UDP NAM) is a critical intermediate in bacterial peptidoglycan (PG) biosynthesis. As the primary source of muramic acid that shapes the PG backbone, modifications installed at the UDP NAM intermediate can be used to selectively tag and manipulate this polymer via metabolic incorporation. However, synthetic and purification strategies to access large quantities of these PG building blocks, as well as their derivatives, are challenging. A robust chemoenzymatic synthesis was developed using an expanded NAM library to produce a variety of 2-N-functionalized UDP NAMs. In addition, a synthetic strategy to access bio-orthogonal 3-lactic acid NAM derivatives was developed. The chemoenzymatic UDP synthesis revealed that the bacterial cell wall recycling enzymes MurNAc/GlcNAc anomeric kinase (AmgK) and NAM α-1 phosphate uridylyl transferase (MurU) were permissive to permutations at the two and three positions of the sugar donor. We further explored the utility of these derivatives in the fluorescent labeling of both Gram (-) and Gram (+) PG in whole cells using a variety of bio-orthogonal chemistries including the tetrazine ligation. This report allows for rapid and scalable access to a variety of functionalized NAMs and UDP NAMs, which now can be used in tandem with other complementary bio-orthogonal labeling strategies to address fundamental questions surrounding PG's role in immunology and microbiology.
- Demeester, Kristen E.,Liang, Hai,Jensen, Matthew R.,Jones, Zachary S.,D'Ambrosio, Elizabeth A.,Scinto, Samuel L.,Zhou, Junhui,Grimes, Catherine L.
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supporting information
p. 9458 - 9465
(2018/07/21)
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- Novel Super-Resolution Imaging Compositions and Methods Using Same
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The invention provides compositions that may be used for imaging intracellular structures. The invention further provides methods of imaging intracellular structures. In certain embodiments, the compositions of the invention include trans-cyclooctene-containing ceramide lipids and tetrazine-containing rhodamine-related dyes.
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- UNNATURAL AMINO ACIDS COMPRISING A CYCLOOCTYNYL OR TRANS-CYCLOOCTENYL ANALOG GROUP AND USES THEREOF
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The present invention relates to unnatural amino acids comprising a cyclooctynyl or trans-cyclooctenyl analog group and having formula (I) or an acid or base addition salt thereof. The invention also relates to the use of said unnatural amino acids, kits and processes for preparation of polypeptides that comprise one or more than one cyclooctynyl or trans-cyclooctenyl analog group. These polypeptides can be covalently modified by in vitro or in vivo reaction with compounds comprising an azide, nitrile oxide, nitrone, diazocarbonyl or 1,2,4,5-tetrazine group.
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- Super-resolution imaging of the Golgi in live cells with a bioorthogonal ceramide probe
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We report a lipid-based strategy to visualize Golgi structure and dynamics at super-resolution in live cells. The method is based on two novel reagents: a trans-cyclooctene-containing ceramide lipid (Cer-TCO) and a highly reactive, tetrazine-tagged near-IR dye (SiR-Tz). These reagents assemble via an extremely rapid "tetrazine-click" reaction into Cer-SiR, a highly photostable "vital dye" that enables prolonged live-cell imaging of the Golgi apparatus by 3D confocal and STED microscopy. Cer-SiR is nontoxic at concentrations as high as 2 μM and does not perturb the mobility of Golgi-resident enzymes or the traffic of cargo from the endoplasmic reticulum through the Golgi and to the plasma membrane.
- Erdmann, Roman S.,Takakura, Hideo,Thompson, Alexander D.,Rivera-Molina, Felix,Allgeyer, Edward S.,Bewersdorf, Joerg,Toomre, Derek,Schepartz, Alanna
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p. 10242 - 10246
(2015/03/31)
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- Preparation of small-molecule microarrays by trans-cyclooctene tetrazine ligation and their application in the high-throughput screening of protein-protein interaction inhibitors of bromodomains
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Fast and efficient: A library of trans-cyclooctene (TCO)-modified small molecules were immobilized on tetrazine-functionalized glass slides by using the fastest bioorthogonal reaction known. The resulting small-molecule microarray was screened against a variety of human bromodomains to identify protein-protein interaction inhibitors. Copyright
- Zhang, Chong-Jing,Tan, Chelsea Y. J.,Ge, Jingyan,Na, Zhenkun,Chen, Grace Y. J.,Uttamchandani, Mahesh,Sun, Hongyan,Yao, Shao Q.
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p. 14060 - 14064
(2014/01/06)
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- Amino acids for diels-alder reactions in living cells
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Under tension: A set of genetically encoded unnatural amino acids can be used for biocompatible site-specific labeling of proteins with fluorogenic dyes. The new compounds have norbornene and trans-cyclooctene units that react with tetrazine derivatives i
- Plass, Tilman,Milles, Sigrid,Koehler, Christine,Szymański, J?drzej,Mueller, Rainer,Wie?ler, Manfred,Schultz, Carsten,Lemke, Edward A.
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supporting information; experimental part
p. 4166 - 4170
(2012/06/01)
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- Diels-alder cycloaddition for fluorophore targeting to specific proteins inside living cells
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The inverse-electron-demand Diels-Alder cycloaddition between trans-cyclooctenes and tetrazines is biocompatible and exceptionally fast. We utilized this chemistry for site-specific fluorescence labeling of proteins on the cell surface and inside living m
- Liu, Daniel S.,Tangpeerachaikul, Anupong,Selvaraj, Ramajeyam,Taylor, Michael T.,Fox, Joseph M.,Ting, Alice Y.
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supporting information; experimental part
p. 792 - 795
(2012/03/07)
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