Article
Chemistry, Multidisciplinary
Yang Gao, Benxiang Zhang, Laura Levy, Hai-Jun Zhang, Chi He, Phil S. Baran
Summary: This article reports the first enantioselective decarboxylative Negishitype alkylations of alpha-oxy carboxylic acids via the intermediacy of redox-active esters (RAEs). The transformation enables the radical-based retrosynthesis of seemingly trivial enantiopure dialkyl carbinols. The article discusses the history of such couplings, the retrosynthetic ramifications, general conditions development, and showcases various applications that demonstrate its simplification effect on synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Review
Chemistry, Multidisciplinary
Sharbil J. Firsan, Vilvanathan Sivakumar, Thomas J. Colacot
Summary: Monoligated palladium(0) species, L1Pd(0), are the most active catalytic species in cross-coupling reactions. Highly active but unstable L1Pd(0) catalysts can be generated from stable precatalysts. The size of the ligand plays a crucial role in the formation of L1Pd(0), and it can be precisely formed from the precatalyst using various technologies.
Article
Chemistry, Multidisciplinary
Shuo Yang, Wei-Tao Jiang, Bin Xiao
Summary: The study focused on tertiary cyclopropyl carbagermatranes obtained through zinc-mediated decarboxylation, which showed efficient reactivity in palladium-catalyzed cross-coupling reactions. They also exhibited orthogonal reactivity with boron reagents, acting as robust nucleophiles for the synthesis of tertiary cyclopropane and efficient intermediates for quaternary center formation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Multidisciplinary Sciences
Benxiang Zhang, Jiayan He, Yang Gao, Laura Levy, Martins S. Oderinde, Maximilian D. Palkowitz, T. G. Murali Dhar, Michael D. Mandler, Michael R. Collins, Daniel C. Schmitt, Philippe N. Bolduc, Teyu Chen, Sebastian Clementson, Nadia Nasser Petersen, Gabriele Laudadio, Cheng Bi, Yu Kawamata, Phil S. Baran
Summary: Modern retrosynthetic analysis in organic chemistry is a method that guides the design of synthetic routes based on the polar relationships between functional groups. This approach assigns charges to functional groups and disconnects bonds between them. It has applications in undergraduate curriculum and synthetic methods, but requires careful considerations to overcome selectivity and oxidation state issues. In this study, a radical-based Ni/Ag-electrocatalytic cross-coupling of substituted carboxylic acids was reported, enabling a simplified approach to accessing complex molecular architectures.
Article
Chemistry, Organic
Lvyin Zheng, Xiaoya Zhuo, Yihan Wang, Xiaoying Zou, Yumei Zhong, Wei Guo
Summary: N,N-disubstituted hydrazides are important pharmaceutical scaffolds in organo-pharmaceutical chemistry. This study reports an efficient method for the synthesis of N,N-disubstituted hydrazides and their bromides from N,N-disubstituted hydrazines and aldehydes through a photoredox-catalytic cross-dehydrogenative coupling reaction. The method offers mild reaction conditions, high regioselectivity, and good functional group tolerance.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Multidisciplinary
Runjhun Tandon, Nitin Tandon, Shripad M. Patil
Summary: Nanocatalysis is an emerging research area that combines the advantages of homogeneous and heterogeneous catalysis. Magnetically recoverable nanocatalysts offer a larger surface area and higher efficiency, leading to improved reaction yields and atom economy.
Article
Chemistry, Physical
Ziyin Kong, Weipeng Hu, James P. P. Morken
Summary: A Pt-catalyzed hydrosilylation reaction of (Z)-1,2-diborylethylene leads to the formation of a 1,2-diboryl-1-silylalkane, which can be used in catalytic cross-coupling reactions. Depending on the catalyst and the reaction conditions, the coupling can occur at either the α or β position relative to the silane center.
Article
Chemistry, Multidisciplinary
Gyumin Kang, Sunkyu Han
Summary: In this study, we successfully synthesized dimeric high-oxidation-state securinega alkaloid Flueggeacosine B via two synthetic routes. The second-generation synthesis was more streamlined and a new reaction was developed to provide a direct pathway for the synthesis of compounds with a conjugated dicarbonyl moiety.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Nanoscience & Nanotechnology
Hongxiao Duan, Lingyan Liang, Zhendong Wu, Hengbo Zhang, Lu Huang, Hongtao Cao
Summary: Optoelectronic synaptic devices with novel channel layers containing p-type CsPbBr3 nanoparticles in an IGZO film show improved visible-light photosensitivity and synaptic plasticity compared to pure IGZO counterparts. The composite device exhibits versatile synaptic behavior under low light stimuli and can imitate complex biological behaviors through gate bias control. This work discusses the band alignment between IGZO and NPs, as well as the excitation and decay processes of intrinsic and photoinduced carriers.
ACS APPLIED MATERIALS & INTERFACES
(2021)
Article
Chemistry, Multidisciplinary
Muriel Durandetti
Summary: The direct formation of C-C bonds catalyzed by nickel complexes has become an important research topic in the past fifty years, and has recently seen a resurgence as a new area in nickel chemistry. This paper provides a summary of the use of nickel complexes in catalysis and highlights the evolution of the authors' own research.
Article
Materials Science, Multidisciplinary
Kezhen Qi, Chunqiang Zhuang, Manjie Zhang, Peyman Gholami, Alireza Khataee
Summary: This review highlights the application of sonochemical synthesis in the preparation of photocatalysts and discusses the sonochemical degradation of pollutants. The progress and future perspective of sonochemical synthesis are summarized, calling for more attention to the research on sonochemical synthesis of materials and promoting its commercialization.
JOURNAL OF MATERIALS SCIENCE & TECHNOLOGY
(2022)
Review
Chemistry, Multidisciplinary
Siqi Sun, Min Lu, Xupeng Gao, Zhifeng Shi, Xue Bai, William W. Yu, Yu Zhang
Summary: 0D perovskites have drawn considerable attention for their unique properties derived from isolated metal halide octahedra or clusters. This review comprehensively analyzes their crystal and electronic structure, as well as properties like large bandgaps, high exciton binding energy, and broad emission spectra from self-trapped excitons with large Stokes shifts. Additionally, synthetic methods and emerging applications in LEDs, solar cells, and detectors are discussed, providing an outlook for future research.
Article
Chemistry, Physical
Souvagya Biswas, Kendra R. Dewese, Balaram Raya, T. RajanBabu
Summary: This study investigates the reactions between ethylene and (E)-2-trialkylsilyloxy-1,3-dienes and their 2-acetoxy derivatives. It is found that using cobalt as the catalyst, the reaction is best conducted at room temperature with methylene chloride as the solvent. Furthermore, it is discovered that two commercially available chiral ligands in combination with cobalt have a significant impact on the regio- and enantioselectivities of the products.
Article
Polymer Science
Qingyi Lu, Dongkui Zhang, Feng Xu, Guohang He, Junning Qian, Jiangbin Xia
Summary: In this study, a novel star-shaped porous fluorescent polyaminocarbazole material was successfully synthesized through chemical oxidation polymerization. The material exhibited a large surface area, high environmental stability, and excellent sensitivity towards metal ions, making it promising for chemical sensors.
EUROPEAN POLYMER JOURNAL
(2022)
Article
Chemistry, Physical
Youxiang Jin, Hao Wen, Feiyan Yang, Decai Ding, Chuan Wang
Summary: In this study, a cross-electrophile strategy was successfully applied to synthesize multisubstituted allenes. Nickel-catalyzed reductive cross-coupling between propargyl carbonates and organoiodides provided a method to prepare tri- or tetrasubstituted allenes without the need for pregenerated organometallics. Furthermore, propargyl carbonates were found to be suitable allenylating agents in nickel-catalyzed asymmetric reductive aryl-allenylation, leading to the formation of chiral benzene-fused cyclic compounds with a quaternary allenyl-substituted stereogenic center in a highly enantioselective manner.
Article
Chemistry, Multidisciplinary
Stephen J. Walsh, Soleilmane Omarjee, Friederike M. Dannheim, Dominique-Laurent Couturier, Dorentina Bexheti, Lee Mendil, Gemma Cronshaw, Toby Fewster, Charlotte Gregg, Cara Brodie, Jodi L. Miller, Richard Houghton, Jason S. Carroll, David R. Spring
Summary: The development of divinylpyrimidine (DVP) reagents for the synthesis of antibody-drug conjugates (ADCs) with in vivo efficacy and tolerability is reported. Detailed structural characterization of the synthesized ADCs was first conducted, followed by in vitro and in vivo evaluation of the ADCs' ability to safely and selectively eradicate target-positive tumors.
CHEMICAL COMMUNICATIONS
(2022)
Correction
Chemistry, Multidisciplinary
Bee Ha Gan, Josephine Gaynord, Sam M. Rowe, Tomas Deingruber, David R. Spring
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Organic
Martin Bargum, Mikkel Krell-Jorgensen, Martin Nielsen, Katrine Qvortrup, Luca Laraia
Summary: This article reports a microfluidic system for photochemical cycloadditions fabricated using silicon micro processing technologies. The optimized system enables the completion of a range of photochemical reactions in just a few minutes using high power UV-LEDs and triplet photosensitizers. The feasibility of performing photochemistry in microflow in an academic research environment is demonstrated, and a reaction leading to a novel scaffold and its mechanistic proposal are reported.
Article
Infectious Diseases
Hannah Ryan, Patrik G. Flammer, Rebecca Nicholson, Louise Loe, Ben Reeves, Enid Allison, Christopher Guy, Ines Lopez Doriga, Tony Waldron, Don Walker, Claas Kirchhelle, Greger Larson, Adrian L. Smith
Summary: This study investigates the prevalence of worm infections in different periods using human burial samples from archaeological sites in England. The results show that the prevalence rates of worm infections varied over time, with significant reductions in some locations during the industrial period. These findings help us understand the factors influencing worm infections in past populations and provide important historical context for controlling worm infections in modern times.
PLOS NEGLECTED TROPICAL DISEASES
(2022)
Article
Biochemistry & Molecular Biology
Cecilia Rossetti, Luca Laraia
Summary: This study systematically investigated the roles of oxysterols in regulating human physiology. It was found that the site of oxidation has a profound impact on target selectivity, with each oxysterol possessing a unique set of target proteins. Additionally, the study revealed that the targets are clustered in pathways related to vesicular transport and phosphoinositide metabolism.
ACS CHEMICAL BIOLOGY
(2022)
Article
Chemistry, Medicinal
Radu Costin Bizga Nicolescu, Zoe R. Maylin, Francisco Javier Perez-Areales, Jessica Iegre, Hardev S. Pandha, Mohammad Asim, David R. Spring
Summary: This study reports the synthesis and biological characterization of a novel class of compounds covalently linking enzalutamide and EPI-001, which show significant improvement in cell killing potency towards prostate cancer cells compared to current therapies. The most promising compounds exhibit toxicity exclusively through androgen receptor mediated pathways, setting the basis for hybrid AR inhibitors combining EPI-001 and enzalutamide into a single molecule.
Article
Biochemistry & Molecular Biology
Thomas Whitmarsh-Everiss, Zhou Wang, Cecilie Hauberg Hansen, Laura Depta, Elisa Sassetti, Oliver Rafn Dan, Axel Pahl, Sonja Sievers, Luca Laraia
Summary: Combining natural product fragments to design new scaffolds with unprecedented bioactivity is an effective strategy for discovering useful compounds for tools and potential therapeutics. However, the choice of fragments to couple and the biological screens to use still remain unanswered questions. In this study, by combining a primary fragment containing the A/B ring system of estradiol with nine different secondary fragments, compounds that modulated four different phenotypes were identified. The use of unbiased morphological profiling with a cell-painting assay also revealed additional phenotypes that were not previously known. The discovery of a variety of biologically active compounds demonstrates the value of recombining natural product fragments with phenotypic screening for rapid compound identification.
Article
Chemistry, Multidisciplinary
Mikkel Krell-Jorgensen, Habiburrahman Zulfikri, Magnus Grage Bonnevie, Frederik Simonsen Bro, Asmus Ougaard Dohn, Luca Laraia
Summary: We report bistable indole-containing hemithioindigos (HTIs) with one-way quantitative photoswitching properties. A mechanism involving isomer-specific excited state intramolecular proton transfer (ESIPT) is proposed based on calculations. We also developed a thermally bistable oligomer-inspired bipyrrole-containing HTI that exhibits large band separation and bidirectional near-quantitative photoisomerization in the near-infrared, bio-optical window.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Nicola Ashman, Jonathan D. Bargh, Stephen J. Walsh, Ryan D. Greenwood, Arnaud Tiberghien, Jason S. Carroll, David R. Spring
Summary: Antibody-drug conjugates with peroxide-cleavable arylboronic acid linkers are developed to target cancer cells with high levels of reactive oxygen species (ROS). These linkers can rapidly release drugs in the presence of hydrogen peroxide while remaining stable in plasma. The peroxide-cleavable ADCs targeting HER2 and PD-L1 exhibit potent cytotoxicity in vitro.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Medicinal
Ruwei Yao, Anders A. A. Jensen, Hogan P. P. Bryce-Rogers, Katrine Schultz-Knudsen, Libin Zhou, Nicklas P. P. Hovendal, Henrik Pedersen, Mariusz Kubus, Trond Ulven, Luca Laraia
Summary: The recombination of natural product fragments is an important strategy for discovering bioactive compounds. We synthesized a compound library enriched in spirocyclic ring fusions using alkaloid-inspired scaffolds. The library exhibited excellent drug-like properties and targeted screening led to the identification of hits with significant agonist or antagonist activity against specific serotonin and dopamine receptors. Optimization of one of these hits resulted in a promising lead compound with high selectivity as a dual 5-HT2B/C antagonist.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Paul Brear, Claudia De Fusco, Eleanor L. Atkinson, Jessica Iegre, Nicola J. Francis-Newton, Ashok R. Venkitaraman, Marko Hyvonen, David R. Spring
Summary: This study describes the development of a series of CK2 alpha allosteric inhibitors through iterative cycles of X-ray crystallography and enzymatic assays, in addition to both fragment growing and fragment merging design strategies. The lead fragment developed, fragment 8, exhibits high ligand efficiency and successful engagement with CK2 alpha in cells.
RSC MEDICINAL CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Nicola Ashman, Jonathan D. Bargh, David R. Spring
Summary: Traditional antibody-drug conjugates (ADCs) require internalisation into cancer cells, but this approach has limitations. Recent research has shown that extracellular release of drugs upon binding to poorly-internalising antigens or other tumoral components can overcome these limitations. This new approach has the potential to expand the range of cancer targets and improve treatment efficacy.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Abigail R. Hanby, Stephen J. Walsh, Andrew J. Counsell, Nicola Ashman, Kim T. Mortensen, Jason S. Carroll, David R. Spring
Summary: In this study, a methodology for the dual-functionalisation of IgG antibodies is developed using disulfide rebridging divinylpyrimidine technology combined with bicyclononyne and methylcyclopropene handles for sequential SPAAC and IEDDA reactions. This strategy is advantageous as it does not require metal catalysis and avoids the need for purification between functionalisation steps.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Friederike M. Dannheim, Stephen J. Walsh, Carolina T. Orozco, Anders Hojgaard Hansen, Jonathan D. Bargh, Sophie E. Jackson, Nicholas J. Bond, Jeremy S. Parker, Jason S. Carroll, David R. Spring
Summary: This study reports a novel method for generating antibody conjugates with modular cargo loading using a new class of disulfide rebridging linkers. The approach allows all four interchain disulfides in an IgG1 antibody to be bridged with a single linker molecule by reacting with eight cysteine residues. Modulation of cargo loading can be achieved in a quick and selective manner by modifying the antibody with the linker in a 1 : 1 ratio and derivatizing the linker with varying numbers of payload attachment handles.
Article
Chemistry, Multidisciplinary
Eleanor L. Atkinson, Jessica Iegre, Claudio D'Amore, Paul Brear, Mauro Salvi, Marko Hyvonen, David R. Spring
Summary: In this study, an iterative cycle of enzymatic assays, X-ray crystallography, molecular modelling and cellular assays was used to develop a functionalisable chemical probe for the investigation of CK2α/β PPI. The lead peptide, P8C9, showed successful binding to CK2α at the PPI site, and it was found to be easily synthesizable and functionalisable. The peptide also exhibited high stability in serum and had potential for further optimization.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
