Article
Chemistry, Multidisciplinary
Anett Hauser, Eleftheria Poulou, Fabian Mueller, Peter Schmieder, Christian P. R. Hackenberger
Summary: The cover of this issue features an image of a phospho-lysine peptide mimic, reflecting a phosphorylated lysine but not identical. Visit the website 10.1002/chem.202003947 for the full article.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Organic
Raffaella Bucci, Francesca Foschi, Camilla Loro, Emanuela Erba, Maria Luisa Gelmi, Sara Pellegrino
Summary: This review emphasizes the recent advances in the design and synthesis of cyclic turn mimics, focusing on their ability to induce gamma-, beta-, and alpha-turns in peptidomimetics.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xinxin Tang, Raj K. Tak, Hidetoshi Noda, Masakatsu Shibasaki
Summary: We report the stereoselective synthesis of remotely decorated, trisubstituted beta-prolines via Rh-catalyzed C-H amination. The method works well in the presence of various functionalities, with carboxylic acids in the products serving as gateways for diverse downstream transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yi-Ming Shi, Jan J. Crames, Laura Czech, Kenan A. J. Bozhuyuk, Yan-Ni Shi, Merle Hirschmann, Stefanie Lamberth, Peter Claus, Nicole Paczia, Christian Ruckert, Jorn Kalinowski, Gert Bange, Helge B. Bode
Summary: This study reveals the biosynthetic potential of a widespread benzobactin gene cluster and identifies the acyl AMP-ligase responsible for the last cyclization step. Genome mining of Pseudomonas chlororaphis uncovered the presence of the gene cluster in different bacterial species, highlighting the regulatory mechanisms and structural diversity of benzobactin biosynthesis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Zachary P. Sercel, Alexander W. Sun, Brian M. Stoltz
Summary: Enantioenriched gem-disubstituted 4-imidazolidinones were prepared in high yield and high enantioselectivity through Pd-catalyzed decarboxylative asymmetric allylic alkylation. A rapid synthetic route starting from 2-thiohydantoin was developed, and the orthogonality of the protecting groups used for nitrogen-rich products was demonstrated, indicating potential applications in drug design.
Article
Nanoscience & Nanotechnology
Gulcihan Gulseren, Aytul Saylam, Antoine Marion, Salih Ozcubukcu
Summary: The introduction of fullerene nanocatalysts into biocatalysis represents a novel approach to mimic enzymatic activity, offering potential for the design of high-efficiency artificial nanocatalysts through self-assembled nanostructures.
ACS APPLIED MATERIALS & INTERFACES
(2021)
Article
Chemistry, Applied
Xuexian Cui, Wen-Chao Geng, Huifeng Jiang, Bian Wu
Summary: Photobiocatalytic cascade is a green synthesis method that efficiently converts biobased feedstocks using the unique reactivity of photocatalysis and biocatalysis. It can modify N-heterocycles with keto acids synthesized from natural amino acids, leading to the synthesis of various important N-heterocyclic derivatives.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Plant Sciences
Dulamini Ekanayake, Bruno Perlatti, Dale C. Swenson, Kadri Poldmaa, Gerald F. Bills, James B. Gloer
Summary: The genus Sphaerostilbella includes fungi that colonize basidiomata of wood-inhabiting fungi, including important forest pathogens. Studies of a isolate collected on the foothills of Himalayas, closely related to S. broomeana isolates from Europe, led to the identification of a new cyclic octapeptide along with related analogues and dioxopiperazines.
JOURNAL OF NATURAL PRODUCTS
(2021)
Article
Chemistry, Multidisciplinary
Ruth Aizen, Zohar A. Arnon, Or Berger, Antonella Ruggiero, Dor Zaguri, Noam Brown, Evgeny Shirshin, Inna Slutsky, Ehud Gazit
Summary: Nucleobase crystals have unique fluorescence properties in the visible spectrum, unlike their monomeric counterparts. Additionally, some nucleobases exhibit a red edge excitation shift, which is uncommon in the field of organic supramolecular materials and may have implications in therapeutic and materials science.
NANOSCALE ADVANCES
(2023)
Article
Chemistry, Multidisciplinary
Johannes Grosskopf, Manuel Plaza, Roger Jan Kutta, Patrick Nuernberger, Thorsten Bach
Summary: 2,5-Diketopiperazines are cyclic dipeptides with a wide range of applications, and their enantioselective preparation can be achieved through photochemical deracemization, allowing for stereochemical editing at a single position while maintaining other stereogenic centers unaffected. The chiral benzophenone catalyst in combination with irradiation at lambda=366 nm enables the establishment of configuration at the stereogenic carbon atom C6 at will.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Infectious Diseases
Rohith Gattu, Sanjay S. Ramesh, Siddaram Nadigar, D. Channe Gowda, Suhas Ramesh
Summary: Peptide-based drugs are gaining momentum in drug discovery, while small molecules-based drugs have been important in drug development for decades. Bridging the gap between peptides and small molecules can be achieved through conjugation chemistry, resulting in attractive benefits and overcoming drawbacks. Molecular hybridization has emerged as a promising approach in medicinal chemistry. This review presents over 125 examples of peptide-small molecule conjugates with therapeutic applications in infectious diseases from 2000 to 2022, showcasing their potential.
Article
Chemistry, Multidisciplinary
Rui Chang, Yubing Pang, Juntao Ye
Summary: This study reports a photoinduced approach for hydroarylation of unactivated olefins using 4-hydroxycoumarins as the arylating reagent. The key to the success of this reaction is the conversion of nucleophilic 4-hydroxycoumarins into electrophilic carbon radicals through photocatalytic arene oxidation. This method not only overcomes the polarity-mismatch issue encountered under ionic conditions but also allows for a broad substrate scope and inhibits side reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Tsukasa Tawatari, Ritsuki Kato, Riku Kudo, Kiyosei Takasu, Hiroshi Takikawa
Summary: In this study, we report on the intramolecular (3+2) cycloaddition reactions between ynamides and benzyne. These reactions involve the formation of two bonds and are facilitated by using benzyne precursors containing a chlorosilyl group. The intermediate indolium ylide in these reactions exhibits both nucleophilic and electrophilic properties at its C2 atom.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yi Gong, Cai Wang, Feng Zhou, Kui Liao, Xi-Yu Wang, Ying Sun, Yan-Xue Zhang, Zhi Tu, Xin Wang, Jian Zhou
Summary: This study presents the first highly selective kinetic resolution of racemic alpha-chiral azides through Cu-catalyzed azide-alkyne cycloaddition (CuAAC). Newly developed pyridine-bisoxazoline (PYBOX) ligands bearing a C4 sulfonyl group enabled effective kinetic resolution and asymmetric CuAAC of racemic azides derived from privileged scaffolds such as indanone, cyclopentenone, and oxindole, leading to alpha-tertiary 1,2,3-triazoles with high to excellent ee values. DFT calculations and control experiments revealed that the C4 sulfonyl group decreased the Lewis basicity of the ligand and increased the electrophilicity of the copper center for better recognition of azides, while also functioning as a shielding group to enhance the efficacy of the chiral pocket of the catalyst.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Wenlong Ding, Chao Liu, Yulin Chen, Jiayu Gu, Chengzhu Fang, Linzhen Hu, Long Zhang, Ying Yuan, Xin-Hua Feng, Shixian Lin
Summary: Protein lipidation, which is important in regulating biological pathways and the pharmaceutical industry, can be synthesized post-translationally. This study presents a computational approach for designing lipidation mimics that mimic the properties of natural lipidation. The researchers also created a system for incorporating these lipidation mimics into proteins, showing their utility in various applications.
NATURE CHEMICAL BIOLOGY
(2023)
Article
Chemistry, Inorganic & Nuclear
Mark Edgar, Mark R. J. Elsegood, Pingchuan Liu, Christopher R. Miles, Martin B. Smith, Shimeng Wu
Summary: This article describes the one-step synthesis of a novel bicyclic diphosphane with good air/solution stability and bridging ligand capability. Various complexes can be formed by reacting this compound with different metal complexes. The structures of these compounds were determined by single crystal X-ray studies.
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Peter De'Ath, Mark R. J. Elsegood, Noelia M. Sanchez-Ballester, Martin B. Smith
Summary: The solid-state behavior of two series of isomeric, phenol-substituted, aminomethylphosphines, as the free ligands and bound to Pt-II, have been extensively studied using single crystal X-ray crystallography, and the corresponding complexes have been successfully synthesized and characterized. Single crystal X-ray structures have been determined for the compounds, revealing various intra- or intermolecular hydrogen contacts leading to different packing arrangements.
Article
Chemistry, Multidisciplinary
Tom D. D'Arcy, Mark R. J. Elsegood, Benjamin R. Buckley
Summary: The highly enantioselective organocatalytic tandem o-HPD-[4+2] reaction described offers a practical method for the synthesis of complex scaffolds. This approach utilizes a chiral oxaziridinium organocatalyst to afford dearomatized products in high enantioselectivity, demonstrating its potential for gram-scale applications.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Optics
Yiwei Liu, Xiaoyu Mao, Xiaohui Wang, Jie Bai, Jun Zhang, Xing Feng, Md. Monarul Islam, Mark R. J. Elsegood, Chuan-Zeng Wang, Takehiko Yamato
Summary: This study synthesized a series of novel pyrene-based hexaarylbenzene molecules and fully characterized them. The experimental results showed that these compounds exhibited tunable emission colors and narrow emission spectra in films, demonstrating clear aggregation-induced emission characteristics. In addition, computational analysis revealed that electronic communication played a crucial role in lowering the quantum yield of these compounds.
JOURNAL OF LUMINESCENCE
(2022)
Article
Chemistry, Multidisciplinary
Christopher A. Halliwell, Sandra E. Dann, Jesus Ferrando-Soria, Felix Plasser, Keith Yendall, Enrique Ramos-Fernandez, Mark R. J. Elsegood, Antonio Fernandez, Goran T. Vladisavljevie
Summary: In this study, a hydrogen-bonded organic framework with hierarchical porosity was reported, and the crystal size could be controlled in a single step. The hierarchical porosity was used for the co-recognition of molecular species and microparticles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Yi Gong, Fei Chen, Jethro Beamish-Cook, Mark R. J. Elsegood, Max Derbyshire, Oliver Rowe, Carl Redshaw
Summary: A series of compounds with different structures were synthesized through solvothermal reactions, which exhibited porous 3D frameworks and could be used as polymerization catalysts. It was found that the choice of solvent and ligands affected both the structure and activity of the products.
Article
Chemistry, Organic
Gazalah S. Mohammed Elgadi, Mark R. J. Elsegood, Miheal Patel, Paulo. A. Netz, Tiag o E. de Oliveira, Marc C. Kimber
Summary: A new family of naphthalenoid C2 symmetric clefts has been synthesized in four steps, resulting in the formation of three C2 symmetric clefts and a rare non-symmetric example. Stereoselective reduction of carbonyl groups at C-8 and C-16 then allows for the generation of cleft molecules with hydrogen bonding potential. Through the use of single-crystal X-ray and computational analysis, the cleft angle of the dione has been determined.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Mark R. J. Elsegood, William Clegg, Carl Redshaw
Summary: The interaction between [VO(OiPr)(3)] and 6-bis(o-hydroxyaryl)pyridine, 2,6-{HOC(Ph)(2)CH2}(2)(NC5H3), LH2, resulted in the formation of [VO(OiPr)L] (1) with high yield. The reaction between LNa2, generated in-situ from LH2 and NaH, and [VCl3(THF)(3)] led to the isolation of [VL2] (2) with cis-pyridyl nitrogen atoms. In the case of [VCl2(TMEDA)(2)], a regioisomer 3.2THF with trans-pyridyl nitrogen atoms was obtained.
Article
Chemistry, Physical
Samuel P. Wallbridge, Stuart Archer, Mark R. J. Elsegood, Jonathan L. Wagner, Jamieson K. Christie, Sandra E. Dann
Summary: Experimental methods showed that ZIF-8 material has a maximum saturation adsorption capacity of 0.36 g g(-1) for n-butanol from aqueous solution. The presence of hydrogen bonding between adsorbed butanol molecules and the formation of butanol clusters were confirmed by DRIFTS. Molecular dynamics simulations revealed the formation of intermolecular hydrogen bonding between the butanol molecules, with an average hydrogen-bond coordination number of 0.9.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Chemistry, Multidisciplinary
Henry J. S. Banks, Josef W. A. Frese, Mark R. J. Elsegood, Carl Redshaw
Summary: In this study, different combinations of organomagnesium reagents and zinc bromide were used to synthesize mixed-metal calix[4]arene systems. These systems showed intriguing molecular structures and were capable of ring opening polymerization of ε-caprolactone under different conditions, producing mixtures of low and high molecular weight products with varying end groups.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Inorganic & Nuclear
Tian Xing, Josef W. A. Frese, Max Derbyshire, Mollie A. Glenister, Mark R. J. Elsegood, Carl Redshaw
Summary: The study synthesized six different structures of zinc calix[4]arene complexes and investigated their structures and activities. These complexes showed activity in the ring opening polymerization of epsilon-caprolactone.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Multidisciplinary
Tian Xing, Max Derbyshire, Mark R. J. Elsegood, Carl Redshaw
Summary: Mixed-metal calix[8]arene systems can be obtained by reacting different combinations of group V alkoxides or tungsten oxyalkoxide salts with p-tert-butylcalix[8]areneH(8) ((LH8)-H-8). These systems exhibit intriguing molecular structures and can undergo ring opening polymerisation of epsilon-caprolactone under N-2, air, or as melts, predominantly yielding low molecular weight products.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Anna Ignaszak, Nigel Patterson, Connor O'Brien, Allison True, Mark R. J. Elsegood, Timothy J. Prior, Carl Redshaw
Summary: Heterometallic cobalt p-tert-butylcalix[6 and 8]arenes have been synthesized and analyzed for their complex structures and electrochemical properties. The results show promising potential for their application due to their good electrochemical activity.
Article
Materials Science, Multidisciplinary
Stephanie Montanaro, Piotr Pander, Jai-Ram Mistry, Mark R. J. Elsegood, Simon J. Teat, Andrew D. Bond, Iain A. Wright, Daniel G. Congrave, Marc K. Etherington
Summary: A critical challenge in thermally activated delayed fluorescence (TADF) is to achieve rapid and efficient electronic transitions with a narrow singlet-triplet energy gap (Delta E-ST) in a single luminophore. This study demonstrates that homoconjugation can be utilized as a viable design strategy to address this challenge. By fusing multiple luminophores across a shared triptycene core, a TADF-active iptycene with homoconjugation was produced, leading to synergistic improvements in photoluminescence quantum yield, singlet decay rate, delayed fluorescence lifetime, and intersystem crossing rate, while narrowing the Delta E-ST. This enhancement is rationalized through TD-DFT calculations considering spin-orbit coupling. The facile synthesis, ubiquity of the pyrazine motif in state-of-the-art TADF materials, and the overall performance enhancement suggest great potential for generality.
JOURNAL OF MATERIALS CHEMISTRY C
(2022)
Article
Chemistry, Physical
Tian Xing, Timothy J. Prior, Mark R. J. Elsegood, Nina V. Semikolenova, Igor E. Soshnikov, Konstantin Bryliakov, Kai Chen, Carl Redshaw
Summary: The synthesis of a series of complexes containing selenophenoxybenzothiazole dyes and their activities in catalyzing ring-opening polymerization reactions were studied. Different structures of complexes were obtained through various chemical reactions, and a positive influence of electron-withdrawing substituents on catalytic activity was observed. These systems showed moderate to good conversions for epsilon-Cl, delta-VL, and co-polymerization, with higher activity observed in the presence of certain electron-withdrawing substituents.
CATALYSIS SCIENCE & TECHNOLOGY
(2021)
