Article
Chemistry, Organic
Koyo Kazama, Rei Kurokawa, Kei Inoue, Hidenori Kinoshita, Katsukiyo Miura
Summary: One-pot synthesis of siloles from readily available starting materials was proposed. This methodology allows for the preparation of multisubstituted siloles in good to excellent yields with complete regioselectivity. Sequential reactions, including lithiation, silylation, and diisobutylaluminum-hydride-promoted cyclization, enable the efficient formation of the siloles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Nanoscience & Nanotechnology
Yanxin Gao, Min-Jeong Suh, Jae-Hong Kim, Gang Yu
Summary: The development of mixed-linker metal-organic frameworks (MOFs) is an effective strategy to enhance their performance. Integrating TCPP into different Zr-MOFs significantly affects the properties of the synthesized materials. TCPP@PCN-777 demonstrates the largest surface area and the highest O-1(2) generation rate. The loading of TCPP also influences the properties of the synthesized MOFs. The optimized TCPP@MOF, TCPP@PCN-777-30, shows high adsorption capacity and efficient degradation of the model contaminant ranitidine (RND) through both adsorption and photodegradation processes.
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Chemistry, Organic
William D. G. Brittain, Steven L. Cobb
Summary: This work utilizes pentafluoropyridine (PFP) in the deoxyfluorination of carboxylic acids to acyl fluorides and in a one-pot amide bond formation. The method allows for high yields of amides to be readily obtained under mild conditions.
Article
Chemistry, Organic
Jie Ma, Xi Wang, Er-Jun Hao, Zhen Shi, Zhi-Bing Dong
Summary: An efficient synthesis method for 1,2-disubstituted indoles has been developed, providing a straightforward route to the target products from easily accessible starting materials. The protocol offers easy performance, high yield, and a broad substrate scope, indicating its potential synthetic value in the preparation of various biologically or pharmaceutically active compounds.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biotechnology & Applied Microbiology
Shota Karakama, Shin Suzuki, Kuniki Kino
Summary: This paper describes a chemoenzymatic method for the synthesis of DKPs in a general-purpose manner with high efficiency under mild conditions. The method allows the synthesis of over 128 types of DKPs without racemization and achieves efficient intramolecular cyclization reactions by controlling pH. The DKPs obtained using this method will provide deeper insights into their structures and functions in future studies.
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Seiji Ogo, Takeshi Yatabe, Tamon Tome, Riko Takenaka, Yoshihito Shiota, Kenji Kato
Summary: This paper reports a method for the synthesis of H2O2 using a homogeneous catalyst in water, using only H2 and O2 without flammable mixtures or cocatalysts. The catalyst can remove electrons from H2, store them for the reduction of O2, and allow the protonation of the reduced oxygen to form H2O2. The turnover number (TON) is 910 under an H2/O2 (95/5) atmosphere (1.9 MPa) for 12 hours at 23 degrees C, which is the highest among any homogeneous catalysts. Furthermore, a reaction mechanism based on two crystal structures is proposed.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Seiji Ogo, Takeshi Yatabe, Tamon Tome, Riko Takenaka, Yoshihito Shiota, Kenji Kato
Summary: In this study, a homogeneous catalyst is used to synthesize hydrogen peroxide using H2 and O2 in water, eliminating the need for flammable H2/O2 mixtures and cocatalysts. The catalyst is capable of extracting electrons from H2, storing them for the reduction of O2, and then converting the reduced oxygen to H2O2. The catalyst exhibits the highest turnover number (TON) among all homogeneous catalysts.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Alex Manicardi, Atiruj Theppawong, Marleen Van Troys, Annemieke Madder
Summary: 1,4-Dione-containing peptides are generated from the cleavage of 2,5-disubstituted furan-containing systems. The generated electrophilic systems react with a-effect nucleophiles, following a Paal-Knorr-like mechanism, to form macrocyclic peptides after resuspension in water. Detailed investigation of the reaction characteristics was performed on supramolecular coiled-coil systems.
Article
Biophysics
Sachiro Kakinoki, Satoru Nishioka, Yuki Arichi, Tetsuji Yamaoka
Summary: This study describes a simple method for the stable coating of biofunctional peptides on the surface of ePTFE using an anchor sequence. The peptide coating promotes the adhesion of endothelial cells and accelerates the formation of neointima-like tissue in vivo.
COLLOIDS AND SURFACES B-BIOINTERFACES
(2022)
Article
Materials Science, Multidisciplinary
Sina Sabury, Ben LaRiviere, M. Nance Ericson, S. Michael Kilbey
Summary: Direct arylation polymerization (DArP) is an efficient method for synthesizing conjugated polymers, and a one-pot strategy involving DArP and Boc deprotection has been successfully used to synthesize a functional adenine-containing poly(alkylthiophene). By controlling the polymerization temperature, quantitative Boc deprotection can be achieved in 24 hours, reducing purification steps and allowing for the production of higher molecular weight polymer. The resulting adenine-containing polythiophene demonstrates hydrogen bonding abilities and superhydrophobic properties on cellulosic filter paper, highlighting the importance of side-chain engineering for functional material design.
ACS APPLIED POLYMER MATERIALS
(2021)
Article
Chemistry, Multidisciplinary
Ming M. Zhang, Zhen Z. Zhan, Meng Wang, He S. Wang, Guo S. Huang
Summary: A base-mediated strategy was utilized to synthesize 2,4,6-trisubstituted pyrimidines from readily available starting materials. The constructed C-C and C-N bonds under transition metal-free conditions resulted in moderate to good yields. This new protocol involves a multicomponent reaction and enables the construction of 2,4,6-trisubstituted pyrimidines from raw materials without the need for further preparation.
Article
Chemistry, Physical
Laura Faba, Juan Gancedo, Jorge Quesada, Eva Diaz, Salvador Ordonez
Summary: This study explores a combined strategy using acid and basic catalysts to enhance the selectivity and efficiency of acetone transformation into mesitylene. After comparing five representative materials, a double bed of Al-MCM-41 and TiO2 is proposed as the optimal approach, resulting in a significant increase in mesitylene productivity through observed synergistic effects.
Article
Chemistry, Organic
Mengyan Duan, Guodong Hou, Yabiao Zhao, Congjun Zhu, Chuanjun Song
Summary: A facile strategy for synthesis of isoxazoles involving oxidation of propargylamines to oximes followed by CuCl-mediated cyclization has been developed. This protocol allows for construction of isoxazole cores with wide functional group compatibility, and can be successfully scaled up for gram-scale experiments and synthetic applications.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Jun-Jie Wang, Rui-Xue Bai, Mao-Qi Yang, Zheng-Yu Chen, Min-Dan Wang, Qian Zhao, Guo-Qiang Lin, Jian-Guo Fu, Chen-Guo Feng
Summary: The total synthesis of (-)-amathaspiramide A was achieved through the efficient construction of a chiral aza-spirobicyclic core using the aldol addition/transamidification cascade. The scope of the efficient construction methodology was investigated, and configuration adjustment via an asymmetric protonation process was identified as a vital step to obtain the correct stereochemistry.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Nilay Kanova, Buse Aysen Dundar, Yilmaz Kelgokmen, Metin Zora
Summary: A one pot two step protocol has been developed for the synthesis of 2-acetyl-1H-pyrroles from N-propargylic beta-enaminones. The method is general, providing a diverse range of products with good to high yields and tolerating various functional groups. This operationally easy method offers a rapid access to functionalized 2-acetyl-1H-pyrroles with potential pharmacological interest.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Plant Sciences
Inmaculada Yruela, Carlos Moreno-Yruela, Christian A. Olsen
Summary: This review provides a comprehensive revision of plant histone deacetylase (HDA) phylogeny and translates recent lessons from other organisms. The evolution of HDAs is correlated with a gain of structural ductility/disorder, similar to other proteins. The authors highlight Brassicaceae-specific HDAs and key mutations affecting the catalytic activity of individual HDAs.
TRENDS IN PLANT SCIENCE
(2021)
Editorial Material
Biochemistry & Molecular Biology
Maria Duca, Dennis Gillingham, Christian Adam Olsen, Gianluca Sbardella, Philip R. Skaanderup, Mario van der Stelt, Boris Vauzeilles, Olalla Vazquez, Yves P. Auberson
Summary: The EFMC is a federation of learned societies in Europe, focusing on the dynamic field spanning chemical biology and medicinal chemistry. The organization aims to drive the development of new drug candidates through the design, synthesis, and optimization of biologically active molecules.
Article
Chemistry, Multidisciplinary
Bengt H. Gless, Benjamin S. Bejder, Fabrizio Monda, Martin S. Bojer, Hanne Ingmer, Christian A. Olsen
Summary: Research has shown that pentameric AIPs presumed to contain thiolactone structures can readily rearrange into homodetic cyclopeptides, leading to implications for a better understanding of cross-species communication in bacteria and potentially guiding the discovery of peptide ligands to disrupt their function.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Multidisciplinary Sciences
Carlos Moreno-Yruela, Di Zhang, Wei Wei, Michael Baek, Wenchao Liu, Jinjun Gao, Daniela Dankova, Alexander L. Nielsen, Julie E. Bolding, Lu Yang, Samuel T. Jameson, Jiemin Wong, Christian A. Olsen, Yingming Zhao
Summary: Lysine L-lactylation is a newly discovered histone modification that is stimulated under conditions of high glycolysis. Through systematic evaluation of histone deacetylases (HDACs), HDAC1-3 and SIRT1-3 were identified as delactylases for this modification. This study provides important insights into the regulatory mechanisms of histone lactylation.
Article
Chemistry, Multidisciplinary
Nima Rajabi, Tobias N. Hansen, Alexander L. Nielsen, Huy T. Nguyen, Michael Baek, Julie E. Bolding, Oskar O. Bahlke, Sylvester E. G. Petersen, Christian R. O. Bartling, Kristian Stromgaard, Christian A. Olsen
Summary: In this study, potent small molecule inhibitors targeting SIRT5 were developed, which showed selective growth inhibition of leukemia cells in culture. This work demonstrates that masked isosteres of carboxylic acids can serve as viable chemical motifs for the development of inhibitors targeting mitochondrial enzymes, with potential applications beyond the sirtuin field.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Medicinal
Carlos Moreno-Yruela, Christian A. Olsen
Summary: This study highlights the importance of thorough kinetic investigation in the development of selective HDAC probes. Potent inhibitors of HDACs 1-3 often display slow-binding kinetics, and this study compares the potencies and selectivities of slow-binding inhibitors measured by discontinuous and continuous assays.
ACS MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Andreas H. Laustsen, Bengt H. Gless, Timothy P. Jenkins, Maria Meyhoff-Madsen, Johanna Bjartun, Andreas S. Munk, Saioa Oscoz, Julian Fernandez, Jose Maria Gutierrez, Bruno Lomonte, Brian Lohse
Summary: The study identified a new peptide (JB006) through phage display technology that can bind to and neutralize the toxic effects of myotoxin II, offering potential for developing inhibitors that can neutralize this toxin.
Article
Chemistry, Multidisciplinary
Julie E. Bolding, Pablo Martin-Gago, Nima Rajabi, Luke F. Gamon, Tobias N. Hansen, Christian R. O. Bartling, Kristian Stromgaard, Michael J. Davies, Christian A. Olsen
Summary: This study demonstrates the use of aryl fluorosulfate electrophiles as covalent inhibitors targeting SIRT5, providing a potential avenue for the development of drug candidates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Bengt H. Gless, Sabrina H. Schmied, Benjamin S. Bejder, Christian A. Olsen
Summary: Thioesters are energy-rich functional groups that can react in an aqueous medium due to their hydrolytic stability at neutral pH. This study investigates the reactivity of thioesters mimicking acyl-coenzyme A (CoA) species and S-acylcysteine modifications, as well as aryl thioesters used in chemical protein synthesis. The researchers developed a fluorogenic assay to directly measure the reaction rate between thioesters and nucleophiles, and found differences in the acylation ability of acetyl- and succinyl-CoA mimics. Furthermore, the study revealed the impact of tris-(2-carboxyethyl)phosphine (TCEP) on native chemical ligation reaction conditions, including potentially harmful hydrolysis side reactions.
Article
Oncology
Dongqing Yan, Anca Franzini, Anthony D. Pomicter, Brayden J. Halverson, Orlando Antelope, Clinton C. Mason, Jonathan M. Ahmann, Anna Senina, Nadeem A. Vellore, Courtney L. Jones, Matthew S. Zabriskie, Hein Than, Michael J. Xiao, Alexandria van Scoyk, Ami B. Patel, Phillip M. Clair, William L. Heaton, Shawn C. Owen, Joshua L. Andersen, Christina M. Egbert, Julie A. Reisz, Angelo D'Alessandro, James E. Cox, Kevin C. Gantz, Hannah M. Redwine, Siddharth M. Iyer, Jamshid S. Khorashad, Nima Rajabi, Christian A. Olsen, Thomas O'Hare, Michael W. Deininger
Summary: SIRT5 is crucial for the survival and growth of AML cells, regardless of genotype, by controlling key metabolic pathways. Inhibiting SIRT5 activity is detrimental to AML cells but well tolerated by healthy hematopoietic cells, making it a potential therapeutic target for AML.
BLOOD CANCER DISCOVERY
(2021)
Article
Biochemistry & Molecular Biology
Alexander L. Nielsen, Nima Rajabi, Norio Kudo, Kathrine Lundo, Carlos Moreno-Yruela, Michael Baek, Martin Fontenas, Alessia Lucidi, Andreas S. Madsen, Minoru Yoshida, Christian A. Olsen
Summary: SIRT2 is a protein deacylase enzyme that influences diverse biological functions in the cell, making it a potential drug target for neurodegenerative diseases and cancer. Researchers have developed a series of chemical probes with potent inhibitory effects on SIRT2-mediated deacetylation and demyristoylation, providing a foundation for future therapeutic development.
RSC CHEMICAL BIOLOGY
(2021)
Article
Biochemistry & Molecular Biology
Kathrin S. Troelsen, Michael Baek, Alexander L. Nielsen, Andreas S. Madsen, Nima Rajabi, Christian A. Olsen
Summary: The study developed a strategy for selectively inhibiting SIRT3 in cells by incorporating mitochondria-targeting peptide sequences into inhibitor structures, demonstrating excellent mitochondrial localization in HeLa cells and target engagement through a cellular thermal shift assay. This selective inhibition showed increased acetylation of the documented SIRT3 target MnSOD in cells, indicating potential for further investigation of SIRT3 as a drug target.
RSC CHEMICAL BIOLOGY
(2021)
Article
Biochemical Research Methods
Carlos Moreno-Yruela, Christian A. Olsen
Summary: Histone deacetylases (HDACs) are enzymes that cleave post-translational e-N-acyllysine modifications. A high-throughput screening protocol is described to identify deacylase activities, with careful optimization of continuous enzyme assays to determine kinetic parameters efficiently. These techniques can aid in inhibitor assay design and provide fundamental understanding of HDAC biochemistry.