Review
Chemistry, Multidisciplinary
Oleksandr S. Liashuk, Vladyslav A. Andriashvili, Andriy O. Tolmachev, Oleksandr O. Grygorenko
Summary: The chemoselective transformations of functionalized sulfonyl fluorides and chlorides have been comprehensively surveyed. Sulfonyl fluorides show excellent selectivity control in their reactions, while sulfonyl chlorides typically react at the SO2Cl moiety except for a few exceptions.
Article
Chemistry, Applied
Luke S. Schembri, Esther Olaniran, Marcus Soderstroem, Bobo Skillinghaug, Luke R. Odell
Summary: This research presents a low temperature and base-free insitu synthesis of diazomethane via a click and release reaction between an enamine and sulfonyl azide. This method can be safely used in organic synthesis and drug discovery programs.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Jose Laxio Arenas, Pascal Retailleau, Jean-Michel Gillet, Nour-Eddine Ghermani, Sandrine Ongeri, Benoit Crousse
Summary: The 5-fluoro triazole amino acid scaffold prepared by halogen exchange was successfully incorporated into peptides. The X-ray diffraction results revealed an important localization of the 5-fluoro triazole motif on one side of the negative potential surface, with the fluorine atom showing a cylindrical shape in its electron density deformation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Alex C. Seastram, Mishra Deepak Hareram, Thomas M. B. Knight, Louis C. Morrill
Summary: An electrochemical method for the azidocyanation of alkenes via 1,4-nitrile migration has been developed. The method is applicable to various alkene containing cyanohydrins and provides access to a broad range of synthetically useful 1,2-azidonitriles. The methodology has also been extended to alkene sulfonylcyanation and the synthesis of a trifunctionalized hexanenitrile.
CHEMICAL COMMUNICATIONS
(2022)
Article
Multidisciplinary Sciences
Yawen You, Qingqing Deng, Yibo Wang, Yanjuan Sang, Guangming Li, Fang Pu, Jinsong Ren, Xiaogang Qu
Summary: This study reports on a DNA-based biocompatible, highly efficient, and precisely targeted copper nanocatalyst, which exhibits excellent catalytic activity and achieves efficient prodrug activation and antitumor effects in cancer cells.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Kian Donnelly, Marcus Baumann
Summary: Microreactors offer excellent reaction control and heat and mass transfer capabilities. Performing chemical reactions under continuous flow conditions allows for increased safety and the utilization of high-energy intermediates. This Synopsis demonstrates the effective use of flow technology in exploiting benzynes, carbenes, and nitrenes in synthetic chemistry programs.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemical Research Methods
Vijay Gulumkar, Antti Aarela, Olli Moisio, Jani Rahkila, Ville Tahtinen, Laura Leimu, Niko Korsoff, Heidi Korhonen, Paivi Poijarvi-Virta, Satu Mikkola, Victor Nesati, Elina Vuorimaa-Laukkanen, Tapani Viitala, Marjo Yliperttula, Anne Roivainen, Pasi Virta
Summary: A 12-armed Buckminster fullerene with azide functional groups was monosubstituted in organic media with cyclooctyne-modified oligonucleotides, leading to the production of molecularly defined monofunctionalized spherical nucleic acids (SNAs). This controlled synthesis scheme allows for one oligonucleotide arm to be functionalized with labels or conjugate groups, while the other arms can remain unmodified or be decorated with different conjugate groups on the outer sphere of the SNAs. Attention was given to the homogeneity and authenticity of the C60-azide scaffold used for assembling the full-armed SNAs.
BIOCONJUGATE CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Frederik Mueggenburg, Sabine Mueller
Summary: This review summarizes the synthetic methods of azide-modified nucleosides and their applications in RNA and DNA functionalization.
Article
Chemistry, Organic
Julian Spils, Thomas Wirth, Boris J. Nachtsheim
Summary: We present a multi-step continuous-flow approach to produce six-membered diaryliodonium salts, with improved scalability and atom economy compared to existing batch methods. Benzyl acetates serve as readily available and cost-effective starting materials in this two-step procedure. An acid-catalyzed Friedel-Crafts alkylation followed by an anodic oxidative cyclization results in a defined set of cyclic iodonium salts, with yield depending on the substrate characteristics.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Abdul Wahab, Ziwei Gao, Jing Gou, Binxun Yu
Summary: Triazole phosphonates are important structural motifs in chemical biology and have gained increasing interest in recent years. A novel method to synthesize triazolyl phosphonates starting from furfuryl phosphonate alcohols and organo-azides using an intermolecular copper-catalyzed cascade reaction was developed. A three-component reaction strategy was realized for rapid access to triazole phosphonates.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Eray Caliskan
Summary: Click chemistry has facilitated the synthesis of polymer compounds. This study successfully synthesized polymer 2 through a chemoselective polymerization reaction, and compared its thermal and dielectric properties with polymer 1.
Article
Chemistry, Applied
Max Roemer, Ian Luck, Nicholas Proschogo
Summary: This paper investigates the synthesis of aryl amines from halobenzenes via copper mediated reactions using sodium azide under mild conditions. The reaction proceeds stepwise through the formation of aryl azides, which are then reduced to amines. The methodology allows for the synthesis of amines from different positions of halobenzenes with electron withdrawing groups. The use of modified stirring bars as heterogeneous catalysts is also demonstrated.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Patrick Pfaff, Felix Anderl, Moritz Fink, Moritz Balkenhohl, Erick M. Carreira
Summary: The study presents a modular approach to novel arylazotriazole photoswitches, with the synthesis of a wide range of organic compounds through copper-catalyzed cycloaddition reactions. These compounds serve as stable intermediates for the synthesis of complex molecules derived from natural products or drugs.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Hiroto Kimura, Kohsuke Aikawa, Takuya Hashimoto
Summary: CuAAC and SuFEx reactions are two important methods for connecting molecules in click chemistry. This study presents a copper-catalyzed aminoazidation reaction using NFC, which attaches both an azide and a fluorosulfonyl group to an alkene in one step. The derivatization of the product through consecutive CuAAC and SuFEx reactions allows rapid diversification of molecular structure.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Hang Han, Bingbin Zhu, Xiaofan Du, Yu Zhu, Chuanming Yu, Xinpeng Jiang
Summary: A novel reaction for the synthesis of 1-azido-3-heteroaryl bicyclo[1.1.1]pentanes via azidoheteroarylation of [1.1.1]propellane is reported. This strategy allows for the direct installation of an azido group, providing an efficient route for synthetic organic chemistry applications.
Article
Virology
Hans Prochnow, Katharina Rox, N. V. Suryanarayana Birudukota, Loreen Weichert, Sven-Kevin Hotop, Philipp Klahn, Kathrin Mohr, Sergej Franz, Dominic H. Banda, Sebastian Blockus, Janine Schreiber, Sibylle Haid, Merel Oeyen, Javier P. Martinez, Roderich D. Suessmuth, Joachim Wink, Andreas Meyerhans, Christine Goffinet, Martin Messerle, Thomas F. Schulz, Andrea Kroeger, Dominique Schols, Thomas Pietschmann, Mark Broenstrup
JOURNAL OF VIROLOGY
(2020)
Review
Infectious Diseases
Philipp Klahn
Article
Infectious Diseases
Yannick Bourgat, Carina Mikolai, Meike Stiesch, Philipp Klahn, Henning Menzel
Summary: The controlled release of antibacterial agents through nanogels has been shown to be effective in managing peri-implant infections. However, the efficacy of the released drug may be hindered by residual linkers. The feasibility of enzyme-triggered drug release has been successfully demonstrated.
Article
Chemistry, Multidisciplinary
Claire Cheyenne Jimidar, Joerg Grunenberg, Bianka Karge, Hazel Leanne Sarah Fuchs, Mark Broenstrup, Philipp Klahn
Summary: This article discusses the development of a novel amino trimethyl lock system for the release of fluorophores, which was successfully applied for imaging H2S in human cells in vitro.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
Mervic D. Kagho, Helen Hintersatz, Andreas Ihle, Haoxuan Zeng, Hedda Schrey, Wera Colisi, Philipp Klahn, Marc Stadler, Clemens Bruhn, Tobias Rueffer, Heinrich Lang, Klaus Banert
Summary: The racemic total synthesis of nitrabirine and its epimer 2-epi nitrabirine was achieved via a six-step route involving biomimetic late-stage heterocyclization. Biological evaluation revealed biofilm dispersal effects against Candida albicans for both compounds, along with moderate antibacterial activities and potent cytotoxic activities for specific derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Analytical
Felix Kaspar, Charity S. G. Ganskow, Lea Eilert, Philipp Klahn, Anett Schallmey
Summary: The report advises against using 5-iodoridine or 5-ethynyluridine as alternative assay reagents in the PUB module due to their lack of an isosbestic point of phosphorolysis under moderately alkaline conditions.
ANALYTICAL CHEMISTRY
(2022)
Review
Chemistry, Organic
Philipp Klahn, Robert Zscherp, Claire C. Jimidar
Summary: Iron is essential for bacterial growth, and bacteria produce and secrete siderophores, such as enterobactin and salmochelins, to ensure their supply of iron. The synthesis and design of these compounds are of great importance for the development of antimicrobial drugs and tools for detecting bacterial infections.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Christian Rohrbacher, Robert Zscherp, Stefanie C. Weck, Philipp Klahn, Christian Ducho
Summary: Overcoming antibiotic resistance requires the development of novel antibacterial agents that target new bacterial cell mechanisms. This study presents a new approach by conjugating a synthetic muraymycin analogue with an enterobactin derivative to enhance cellular uptake and improve antibacterial activity against Gram-negative bacteria.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Christa Kanstrup, Claire C. Jimidar, Josip Tomas, Giuliano Cutolo, Christoph Crocoll, Marie Schuler, Philipp Klahn, Arnaud Tatibouet, Hussam Hassan Nour-Eldin
Summary: Glucosinolate transporters (GTR1/2/3) from the NPF family are crucial for the transport, accumulation, and distribution of glucosinolates. By synthesizing fluorescent glucosinolates, the ability of GTR1/2/3 from Arabidopsis thaliana to import these compounds was investigated. Five out of seven fluorescent glucosinolates were successfully imported by at least one GTR. The uptake mechanism of fluorescent glucosinolates was found to be similar to that of natural glucosinolates.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Medicinal
Lunan Jian, Robert Zscherp, Ulrike Beutling, Xiaofei Shen, Shiyang Xu, Xia Zhang, Mark Broenstrup, Philipp Klahn, Qingxiang Sun
Summary: In this study, four aminoratjadone derivatives were synthesized and two of them, KL1 and KL2, were found to be noncovalent CRM1 inhibitors. The compounds underwent spontaneous hydrolysis in aqueous buffers and the resulting products showed higher activity against CRM1. High-resolution crystal structures revealed the binding mode of these compounds to CRM1 and explained the structure-activity relationships. In cells, KL1 and KL2 localized CRM1 in the nuclear periphery and led to depletion of nuclear CRM1, thereby inhibiting the nuclear export and growth of colorectal cancer cells at submicromolar concentrations. This work lays the foundation for further development of aminoratjadone-based noncovalent CRM1 inhibitors.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Robert Zscherp, Aishi Chakrabarti, Anna P. Lehmann, Hedda Schrey, Hoaxuan Zeng, Wera Collisi, Philipp Klahn
Summary: 6,7-dihydroxycoumarin-5-carboxylates DHCou and 4-Me-DHCou were synthesized via a five-step route, including a propargyl-Claisen rearrangement as a key step. These compounds exhibit antibiofilm activity against Stapylococcus aureus and Candida albicans but lack the cytotoxic activity of parent 6,7-dihydroxycoumarines such as esculetin and 4-methylesculetin.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Oliver Hennrich, Leoni Weinmann, Andreas Kulik, Karen Harms, Philipp Klahn, Jung-Won Youn, Frank Surup, Yvonne Mast
Summary: This study reports a mutasynthesis approach for the derivation of antimicrobial drugs, targeting the phenylglycine residue. Through mutasynthesis with halogenated phenylglycine derivatives, two new natural compounds, 6-chloropristinamycin I and 6-fluoropristinamycin I, were produced. The developed whole-cell biotransformation process demonstrated an advanced level of mutasynthesis.
RSC CHEMICAL BIOLOGY
(2023)
Article
Materials Science, Multidisciplinary
Martin Menzler, Charity S. G. Ganskow, Maximilian Ruschig, Essam Moustafa, Volker Sittinger, Kristina Lachmann, Esther Veronika Wenzel, Giulio Russo, Philipp Klahn, Jan Gaebler
Summary: To control virus pandemics, fast and precise virus detection methods are necessary. Recent studies have shown that electrochemical impedance spectroscopy can accurately and quickly detect viruses. Initial tests using boron-doped diamond as a high-performance electrode material for biosensing showed promising results, although further research and improvement are needed.
C-JOURNAL OF CARBON RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Robert Zscherp, Janetta Coetzee, Johannes Vornweg, Joerg Grunenberg, Jennifer Herrmann, Rolf Mueller, Philipp Klahn
Summary: The design, synthesis, and biological evaluation of the artificial enterobactin analogue Ent(KL) and its fluorophore-conjugates are described in this study. Ent(KL) can promote the growth of Gram-negative pathogens and has a iron binding constant similar to natural enterobactin. The conjugates are recognized by outer membrane siderophore receptors and can deliver molecular cargos to bacterial cells.
Article
Chemistry, Multidisciplinary
Philipp Klahn, Verena Fetz, Antje Ritter, Wera Collisi, Bettina Hinkelmann, Tatjana Arnold, Werner Tegge, Katharina Rox, Stephan Huettel, Kathrin Mohr, Joachim Wink, Marc Stadler, Josef Wissing, Lothar Jaensch, Mark Broenstrup