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Click chemistry

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https://www.readbyqxmd.com/read/28430422/gauging-donor-acceptor-properties-and-redox-stability-of-chelating-click-derived-triazoles-and-triazolylidenes-a-case-study-with-rhenium-i-complexes
#1
Lisa Suntrup, Sinja Klenk, Johannes Klein, Sebastian Sobottka, Biprajit Sarkar
Bidentate ligands containing at least one triazole or triazolylidene (mesoionic carbene, MIC) unit are extremely popular in contemporary chemistry. One reason for their popularity is the similarities as well as differences in the donor/acceptor properties that these ligands display in comparison to their pyridine or other N-heterocyclic carbene counterparts. We present here seven rhenium(I) carbonyl complexes where the bidentate ligands contain combinations of pyridine/triazole/triazolylidene. These are the first examples of rhenium(I) complexes with bidentate 1,2,3-triazol-5-ylidene-containing ligands...
April 21, 2017: Inorganic Chemistry
https://www.readbyqxmd.com/read/28429685/interlayer-crosslinked-micelles-prepared-from-star-shaped-copolymers-via-click-chemistry-for-sustained-drug-release
#2
Xiaojin Zhang, Hongquan Wang, Yu Dai
To balance the stability and the particle size of polymeric micelles, star-shaped copolymers Hx-yne-N3-PEG containing both alkynyl and azido groups were synthesized from hyperbranched 2,2-bismethylolpropionic acid polyester (H20 with 16 hydroxyl, H30 with 32 hydroxyl, H40 with 64 hydroxyl) to develop interlayer-crosslinked micelles by click chemistry. The results of dynamic light scattering indicate that the crosslinking could enhance the stability of polymeric micelles. The crosslinked micelles are regular nanosized (approximately 20 nm) spheres observed by a transmission electron microscope...
April 21, 2017: Nanotechnology
https://www.readbyqxmd.com/read/28429026/n-difluoromethyl-triazole-as-a-constrained-scaffold-in-peptidomimetics
#3
M Mamone, R S B Gonçalves, F Blanchard, G Bernadat, S Ongeri, T Milcent, B Crousse
The N-difluoromethyl triazolo-β-aza-ε-amino acid present in the core of peptides led to constrained conformations due to CH-F and NH-F interactions. Pseudotetrapeptides were obtained in excellent yields directly by click chemistry between azidodifluoroacetamides and alkynes, both linked to an amino acid. This work demonstrates that the N-difluoromethyltriazole scaffold can induce extended structures to β-strand mimics.
April 21, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28426192/profiling-cellular-substrates-of-lysine-acetyltransferases-gcn5-and-p300-with-orthogonal-labeling-and-click-chemistry
#4
Zhen Han, Chau-Wen Chou, Xiangkun Yang, Michael G Bartlett, Y George Zheng
p300 and GCN5 are two representative histone/lysine acetyltransferase (HAT/KAT) enzymes in mammalian cells. It was recently reported that they possess multiple acyltransferase activities including acetylation, propionylation, and butyrylation of the -amino group of lysine residues of histones and non-histone protein substrates. Although thousands of acetylated substrates and acetylation sites have been identified by mass spectrometry-based proteomic screening, our knowledge about protein acylation, especially the causative connection between individual KAT members and their substrates remain limited...
April 20, 2017: ACS Chemical Biology
https://www.readbyqxmd.com/read/28426149/click-chemistry-mediated-rapid-microbubble-catching-for-acute-thrombus-ultrasound-molecular-imaging
#5
Tuantuan Wang, Chuxiao Yuan, Bingyang Dai, Yang Liu, Mingxi Li, Zhenqiang Feng, Qing Jiang, Zhihong Xu, Ningwei Zhao, Ning Gu, Fang Yang
Bioorthogonal coupling chemistry has been studied as one significant advantage for molecular imaging as it offers rapid, efficient, and strong binding, which may also benefit in stability, production, and chemical conjugation. The inverse-electron-demand Diels-Alder reaction between s-tetrazine and trans-cyclooctene (TCO) is an example of a highly selective and rapid bioorthogonal coupling reaction to be used successfully to prepare targeted molecular imaging probes. Herein, based on a two-step pretargeting bioorthogonal chemistry, we report a fast and reliable highly sensitive approach to achieve activated-platelet-specific CD62p targeted thrombus ultrasound molecular imaging...
April 20, 2017: Chembiochem: a European Journal of Chemical Biology
https://www.readbyqxmd.com/read/28425464/metabolic-labelling-of-the-carbohydrate-core-in-bacterial-peptidoglycan-and-its-applications
#6
Hai Liang, Kristen E DeMeester, Ching-Wen Hou, Michelle A Parent, Jeffrey L Caplan, Catherine L Grimes
Bacterial cells are surrounded by a polymer known as peptidoglycan (PG), which protects the cell from changes in osmotic pressure and small molecule insults. A component of this material, N-acetyl-muramic acid (NAM), serves as a core structural element for innate immune recognition of PG fragments. We report the synthesis of modifiable NAM carbohydrate derivatives and the installation of these building blocks into the backbone of Gram-positive and Gram-negative bacterial PG utilizing metabolic cell wall recycling and biosynthetic machineries...
April 20, 2017: Nature Communications
https://www.readbyqxmd.com/read/28417588/a-scalable-and-versatile-synthesis-of-oxime-based-hormone-dimers-and-gels-for-sustained-release
#7
Christopher W Bennett, Joe Collins, Zeyun Xiao, Daniel Klinger, Luke A Connal
Well-defined steroid hormone dimers and organogels were produced via a facile and scalable synthesis using oxime click chemistry. The versatile synthetic procedure extends to a wide range of hormones and linker groups exemplified here through the synthesis of cortisol- and progesterone-dimers linked via hydrophobic, hydrophilic or functional groups. This method was also extended to the synthesis of cortisone-based organogels. Owing to the dynamic nature of the oxime bond, the hormone-based materials are degradable via acidic hydrolysis and transoximination representing new materials for the controlled release of steroid hormones...
April 18, 2017: Chemistry, An Asian Journal
https://www.readbyqxmd.com/read/28414900/precision-templated-bottom-up-multiprotein-nanoassembly-through-defined-click-chemistry-linkage-to-dna
#8
Gabriella Marth, Andrew M Hartley, Samuel C Reddington, Lauren L Sargisson, Marlène Parcollet, Katherine E Dunn, D Dafydd Jones, Eugen Stulz
We demonstrate an approach that allows attachment of single-stranded DNA (ssDNA) to a defined residue in a protein of interest (POI) so as to provide optimal and well-defined multicomponent assemblies. Using an expanded genetic code system, azido-phenylalanine (azF) was incorporated at defined residue positions in each POI; copper-free click chemistry was used to attach exactly one ssDNA at precisely defined residues. By choosing an appropriate residue, ssDNA conjugation had minimal impact on protein function, even when attached close to active sites...
April 20, 2017: ACS Nano
https://www.readbyqxmd.com/read/28411638/approaches-for-conjugating-tailor-made-polymers-to-proteins
#9
Matthew Paeth, Jacob Stapleton, Melissa L Dougherty, Henry Fischesser, Jerry Shepherd, Matthew McCauley, Rebecca Falatach, Richard C Page, Jason A Berberich, Dominik Konkolewicz
A series of methods are outlined for attaching functional polymers to proteins. Polymers with good control over structure, functionality, and composition can be created using reversible addition-fragmentation chain transfer (RAFT) polymerization. These polymers can be covalently linked to enzymes and proteins using either the "grafting-to" approach, where a preformed polymer is attached to the protein surface, or the "grafting-from" approach, where the polymer is grown from the protein surface. Methods for grafting-to, or attaching the RAFT chain transfer agent to the protein surface outlined include the commonly used carbodiimide/activated ester (EDC/NHS) coupling...
2017: Methods in Enzymology
https://www.readbyqxmd.com/read/28400608/development-of-mixed-metal-metal-organic-polyhedra-networks-colloids-and-mofs-and-their-pharmacokinetic-applications
#10
Nazir Ahmad, Hussein A Younus, Adeel H Chughtai, Kristof Van Hecke, Muhammad Danish, Zhang Gaoke, Francis Verpoort
The coordination networking of discrete metal-organic polyhedra (MOPs) involving different ligands as well as metals is a challenging task due to the features of limited solubility and chemical stability of these polyhedra. An unusual approach, ligand-oriented polyhedral networking via click chemistry and further metal coordination is reported here. An alkyne decorated Cu(II)-MOP self-catalyzes the regioselective click reaction (1,3-dipolar cycloaddition) using azide-functionalized ligands under unconventional reaction conditions...
April 11, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28399460/molecular-imaging-based-on-metabolic-glycoengineering-and-bioorthogonal-click-chemistry
#11
REVIEW
Hong Yeol Yoon, Heebeom Koo, Kwangmeyung Kim, Ick Chan Kwon
Metabolic glycoengineering is a powerful technique that can introduce various chemical groups to cellular glycan by treatment of unnatural monosaccharide. Particularly, this technique has enabled many challenging trials for molecular imaging in combination with click chemistry, which provides fast and specific chemical conjugation reaction of imaging probes to metabolically-modified live cells. This review introduces recent progress in molecular imaging based on the combination of these two cutting-edge techniques...
April 4, 2017: Biomaterials
https://www.readbyqxmd.com/read/28398751/ligand-characteristics-important-to-avidity-interactions-of-multivalent-nanoparticles
#12
Ming-Hsin Li, Hong Zong, Pascale R Leroueil, Seok Ki Choi, James R Baker
Multivalent interactions involve the engagement of multiple ligand-receptor pairs and are important in synthetic biology as design paradigms for targeted nanoparticles (NPs). However, little is known about the specific ligand parameters important to multivalent interactions. We employed a series of oligonucleotides as ligands conjugated to dendrimers as nanoparticles, and used complementary oligonucleotides on a functionalized SPR surface to measure binding. We compared the effect of ligand affinity to ligand number on the avidity characteristics of functionalized NPs...
April 11, 2017: Bioconjugate Chemistry
https://www.readbyqxmd.com/read/28396548/click-chemistry-facilitated-structural-diversification-of-nitrothiazoles-nitrofurans-and-nitropyrroles-enhances-antimicrobial-activity-against-giardia-lamblia
#13
Wan Jung Kim, Keith Korthals, Suhua Li, Christine Le, Jaroslaw Kalisiak, K Barry Sharpless, Valery V Fokin, Yukiko Miyamoto, Lars Eckmann
Giardia lamblia is an important and ubiquitous cause of diarrheal disease. The primary agents in the treatment of giardiasis are nitroheterocyclic drugs, particularly the imidazoles metronidazole and tinidazole, and the thiazole, nitazoxanide. Although these drugs are generally effective, treatment failures occur in up to 20% of cases and resistance has been demonstrated in vivo and in vitro. Prior work had suggested that side chain modifications of the imidazole core can lead to effective new 5-nitroimidazole drugs that can combat nitro drug resistance, but the full potential of nitroheterocycles other than imidazole to yield effective new antigiardial agents has not been explored...
April 10, 2017: Antimicrobial Agents and Chemotherapy
https://www.readbyqxmd.com/read/28394504/systematic-identification-of-the-protein-substrates-of-udp-galnac-polypeptide-n-acetylgalactosaminyltransferase-t1-t2-t3-using-a-human-proteome-microarray
#14
Zhijue Xu, Xing Li, Shumin Zhou, Wenxian Xie, Jing Wang, Li Cheng, Sheng Wang, Shujuan Guo, Zhaowei Xu, Xin Cao, Menghui Zhang, Biao Yu, Hisashi Narimatsu, Sheng-Ce Tao, Yan Zhang
O-GalNAc glycosylation is the initial step of the mucin-type O-glycosylation. In humans, it is catalyzed by a family of 20 homologous UDP-GalNAc:polypeptide N-acetylgalactosaminyltransferases (ppGalNAc-Ts). So far, there is very limited information on their protein substrate specificities. In this study, we developed an on-chip ppGalNAc-Ts assay which could rapidly and systematically identify the protein substrates of each ppGalNAc-T. In detail, we utilized a human proteome microarray as the protein substrates and UDP-GalNAz as the nucleotide sugar donor for click chemistry detection...
April 10, 2017: Proteomics
https://www.readbyqxmd.com/read/28391052/bio-orthogonal-conjugation-and-enzymatically-triggered-release-of-proteins-within-multi-layered-hydrogels
#15
Chen Guo, Heejae Kim, Elisa M Ovadia, Christine M Mourafetis, Mingrui Yang, Wilfred Chen, April M Kloxin
Hydrogels are facile architectures for the controlled presentation of proteins with far-reaching applications, from fundamental biological studies in three-dimensional culture to new regenerative medicine and therapeutic delivery strategies. Here, we demonstrate a versatile approach for spatially-defined presentation of engineered proteins within hydrogels through i) immobilization using bio-orthogonal strain-promoted alkyne-azide click chemistry and ii) dynamic proteasedriven protein release using exogenously applied enzyme...
April 5, 2017: Acta Biomaterialia
https://www.readbyqxmd.com/read/28387405/supramolecular-chemistry-of-pillar-n-arenes-functionalised-by-a-copper-i-catalysed-alkyne-azide-cycloaddition-click-reaction
#16
T Kakuta, T Yamagishi, T Ogoshi
Since we discovered pillar[n]arenes in 2008, many chemists have developed a strong interest in pillar[n]arene chemistry because of the many advantages associated with these materials, including their facile and high yielding synthesis, versatile functionality, planar chirality and unique host-guest properties. In this feature article, we discuss recent advances in the field of supramolecular chemistry based on the use of pillar[n]arenes as substrates for copper(i)-catalysed alkyne-azide cycloaddition (CuAAC) "click" chemistry...
April 7, 2017: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/28385214/dual-crosslinked-chondroitin-sulfate-injectable-hydrogel-formed-via-continuous-diels-alder-da-click-chemistry-for-bone-repair
#17
Xiao Bai, Shaoyu Lü, Zhen Cao, Boli Ni, Xin Wang, Piao Ning, Dongyang Ma, Hua Wei, Mingzhu Liu
In the present work, a thermosensetive copolymer with a low gelation concentration under 37°C, F127@ChS (F127 crosslinked chondroitin sulfate) was synthesized via DA click chemistry between F127-AMI (maleimido terminated F127) and ChS-furan (furfurylamine grafted chondroitin sulfate). Then, dual crosslinked hydrogels were prepared based on F127@ChS and PEG-AMI (maleimido terminated polyethylene glycol). The physical crosslinking of F127@ChS affords the hydrogel fast gelation behavior, while in situ DA click reaction occurred between F127@ChS and PEG-AMI affords the hydrogel system covalent crosslinking...
June 15, 2017: Carbohydrate Polymers
https://www.readbyqxmd.com/read/28382823/tandem-oligonucleotide-probe-annealing-and-elongation-to-discriminate-viral-sequence
#18
Maria Taskova, Jesper Uhd, Laura Miotke, Matthew Kubit, John Bell, Hanlee P Ji, Kira Astakhova
New approaches for genomic DNA/RNA detection are in high demand in order to provide controls for existing enzymatic technologies and to create alternatives for emerging applications. In particular, there is an unmet need in rapid, reliable detection of short RNA regions which could open up new opportunities in transcriptome analysis, virology, and other fields. Herein, we report for the first time a "click" chemistry approach to oligonucleotide probe elongation as a novel approach to specifically detect a viral sequence...
April 7, 2017: Analytical Chemistry
https://www.readbyqxmd.com/read/28382203/clickin-a-flexible-protocol-for-quantifying-mitochondrial-uptake-of-nucleobase-derivatives
#19
Kurt Hoogewijs, Andrew M James, Robin A J Smith, Frank Abendroth, Michael J Gait, Michael P Murphy, Robert N Lightowlers
There is an increasing interest in targeting molecules to the mitochondrial matrix. Many proteins are naturally imported through the translocase complexes found in the outer and inner mitochondrial membranes. One possible means for importing molecules is therefore to use a mitochondrial pre-protein as a vector and assess what forms of molecules can be attached to the pre-protein as cargo. A major difficulty with this approach is to ensure that any chimaeric molecule does indeed access the mitochondrial matrix and does not merely associate with the mitochondrial membranes...
April 6, 2017: Interface Focus
https://www.readbyqxmd.com/read/28380333/synthesis-and-characterization-of-a-biocompatible-chitosan-based-hydrogel-cross-linked-via-click-chemistry-for-controlled-drug-release
#20
O Guaresti, C García-Astrain, T Palomares, A Alonso-Varona, A Eceiza, N Gabilondo
A chemically cross-linked chitosan-based hydrogel was successfully synthesized through Diels-Alder (DA) reaction and characterized. The final product was obtained after different steps; on the one hand, furan-modified chitosan (Cs-Fu) was synthesized by the reaction of furfural with the free amino groups of chitosan. On the other hand, highlighting the novelty of the present research, maleimide-functionalized chitosan (Cs-AMI) was prepared by the reaction of a maleimide-modified aminoacid with the amino groups of chitosan through amide coupling...
April 2, 2017: International Journal of Biological Macromolecules
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