Article
Chemistry, Organic
Tanveer Ahmad, Feng Gao, Jing Li, Zhenfeng Zhang, Tao Song, Qianjia Yuan, Wanbin Zhang
Summary: TBAJ-587, an analogue of bedaquiline (BDQ), exhibits high bacterial potency, low toxicity, and improved pharmacokinetic profile compared to the parent molecule. The first asymmetric synthesis of TBAJ-587 using a synergistic Li/Li bimetallic system is reported, achieving a yield of 90% and an enantiomeric ratio of 80:20. This efficient synthesis method can be scaled up for clinical drug production.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Yin-Xia Sun, Wen-Yu Han, Zhe-Peng Deng, Yi-Gang Sun, Yue-Hui Jia, Yu Sun, Shu-Zhen Zhang
Summary: A multifunctional fluorescent sensor Zn-MOF was prepared by hydrothermal reaction, and it exhibited high selectivity and sensitivity to detect HSO4 or Glu/Asp by Turn Off the emission. Furthermore, the in situ generated [Zn-MOF + Glu/Asp] system was used for the relay detection of Arg/Lys without separation and purification, with a new fluorescence Turn On signal under the same conditions. The sensing process showed outstanding cost-saving, rapid responsiveness, and recyclability in aqueous solution.
INORGANICA CHIMICA ACTA
(2023)
Article
Environmental Sciences
Adeel ur Rehman, Abdulrab Abdulwahab, Asrajjit Kaur, Muhammad Saad Khan, Dzulkarnain B. Zaini, AzmiB. M. Shariff, Bhajan Lal
Summary: This study investigates the effect of Diethylene glycol (DEG) and Glycine (Gly) mixtures on the formation of carbon dioxide hydrates through experimental and modeling methods. The findings suggest that the mixture can inhibit hydrate formation at certain concentrations, with the best results observed at 15 wt% concentration of DEG and Gly. Additionally, a freezing point model is applied to predict hydrate data, and the results show satisfactory agreement with experimental results.
Article
Chemistry, Multidisciplinary
Liang Wei, Chun-Jiang Wang
Summary: Azomethine ylides are important intermediates for the construction of chiral N-containing compounds. Through synergistic catalysis and azomethine ylide chemistry, novel catalytic systems have been developed to convert readily available azomethine ylides into high-valued molecules. The synergistic catalyst system shows enhanced catalytic efficiency and chiral induction ability compared to traditional mono-catalysis, and can be applied in the synthesis of bioactive compounds and natural products.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Miaolin Ke, Yuyan Yu, Longwu Sun, Xinzhi Li, Qianqian Cao, Xiao Xiao, Fener Chen
Summary: A synergistic palladium/copper catalysis for the asymmetric allylic alkylation of vinylethylene carbonates with aldimine esters has been developed for the synthesis of alpha-quaternary (Z)-trisubstituted allylic amino acids under mild conditions. This methodology demonstrates broad substrate compatibility with yields up to 87% and up to 94% ee. The facile scale-up and straightforward conversion to 1,2,3,5-tetrasubstituted pyrrole and 1,2,5,6-tetrahydropyridine bearing chiral quaternary carbon centers confirm the synthetic utility of this method.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Ling Zhao, Yicong Luo, Junzhe Xiao, Xiaohong Huo, Shengming Ma, Wanbin Zhang
Summary: The stereodivergent synthesis of allene compounds with adjacent chiralities has been achieved through Pd/Cu-catalyzed dynamic kinetic asymmetric alkylation. The matched reactivity of a bimetallic catalytic system allows for a smooth reaction of racemic aryl-substituted allenylic acetates with sterically crowded aldimine esters. Various chiral non-natural amino acids with a terminal allenyl group can be easily synthesized with high yields and excellent diastereo- and enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Nanoscience & Nanotechnology
Lihui Liu, Ruimin Dong, Honggang Ge, Junxian Piao, Yun Wang, Shuling Li, Wei Shen, Kun Cao, Shufen Chen
Summary: This research demonstrates that interfacial engineering of the hole transport layer is a reliable strategy for enhancing the device efficiency and operation stability of blue perovskite light-emitting diodes (PeLEDs).
ACS APPLIED MATERIALS & INTERFACES
(2022)
Article
Pharmacology & Pharmacy
Karen Perez-Carreon, Luz Maria Martinez, Marcelo Videa, Jorge Cruz-Angeles, Jimena Gomez, Emilio Ramirez
Summary: This study determined the effective molar ratio of arginine and lysine to folic acid (FA) that maximized solubility using conductimetric titration. Binary formulations were prepared, resulting in an amorphous system with significantly increased solubility and morphology dependent on the preparation method. These findings are important for enhancing solubility and scaling purposes.
Article
Chemistry, Organic
Fan Wu, Zhiming Li, Chao Fu, Guan Wang, Changwu Zheng, Xiaoyu Wu
Summary: The asymmetric α-allylation of α-aryl-substituted 2-acetylimidazoles using Ni/Pd catalysts was successfully developed. The reaction involves the activation of the enolate of an acetyl imidazole by a nickel-bisoxazoline complex, followed by a reaction with a π-allylpalladium electrophile generated from an allyl alcohol derivative using a palladium-based catalyst. The broad substrate scope and the gram-scale reaction demonstrated the utility of this method.
Article
Chemistry, Multidisciplinary
Zhen Yu, Dale F. Kreitler, Yin Ting T. Chiu, Ruiwen Xu, Austin T. Bruchs, Craig A. Bingman, Samuel H. Gellman
Summary: Peptide engineering has successfully delivered drugs for various human diseases. While side chain alteration is a common strategy, the modification of peptide backbone has received less attention. This study demonstrates that rational and coordinated side chain modification and backbone extension can engineer new and favorable contacts between target proteins and synthetic peptide ligands. These findings support the synergy between backbone and side chain modification in ligands of the parathyroid hormone receptor-1, motivating the adoption of coordinated modifications to enhance peptide ligand engagement with target proteins.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Yin Yuan, Junfeng Yang, Junliang Zhang
Summary: In this study, a Cu-catalyzed enantioselective decarboxylative cyanation method via the merger of photocatalysis and electrochemistry was reported. This method provides an efficient and straightforward approach for decarboxylative coupling, eliminating the need for stoichiometric chemical oxidants or substrate prefunctionalization. Mechanistic insight on enantioselectivity control was obtained through DFT calculations.
Article
Chemistry, Physical
Md Sajjadur Rahman, Ranen Roy, Cynthia Montoya, Mohammad A. Halim, Douglas E. Raynie
Summary: Amino acid-based deep eutectic solvents (AADESs) were formulated and their interactions were investigated using FT-IR, 1H NMR spectroscopy, and mass spectrometry. Glu-Gly was found to form ester impurities, but they were negligible according to mass spectrometry. TGA showed that both DESs could be used up to 150-160 degrees C. PCA helped visualize the spectroscopic outcomes. Glu-Gly was more efficient for lignin depolymerization.
JOURNAL OF MOLECULAR LIQUIDS
(2022)
Article
Chemistry, Physical
Haizatul Hafizah Hussain, Hazlina Husin
Summary: Gas hydrates solid deposition in pipelines has caused critical flow assurance issues, especially in the transportation of hydrocarbons. Mechanical and chemical methods can be used to mitigate gas hydrate occurrences, with the latter being found more feasible. Ionic liquids and amino acids have dual function capabilities in inhibiting hydrates, and their synergistic performances were investigated in this research. Experimental testing for the unlimited number of cationic and anionic combinations of AACILs is time-consuming and costly, so a pre-screening approach was used to study their potential using COSMO-RS software. Among 91 studied synergistic AACILs, choline aspartate showed the highest performance as a hydrate inhibitor.
JOURNAL OF MOLECULAR LIQUIDS
(2021)
Article
Agriculture, Multidisciplinary
Rocio Gutierrez-Escobar, Maria Jose Aliano-Gonzalez, Almudena Marrufo-Curtido, Maria Jesus Jimenez-Hierro, Belen Puertas, Emma Cantos-Villar
Summary: The effectiveness of various preservatives in protecting Verdejo white wines was investigated in this study. The results showed that the stilbene-enriched extract preserved the wines from malolactic fermentation and maintained their quality parameters, but affected their color. Synergistic effects between the stilbene extract and glutathione were found for oxidation processes. The content of amino acids and biogenic amines was minimally affected by the treatments, and the quality or safety of the wines was not compromised. However, after 12 months of ageing, wines treated with sulfur dioxide showed the highest score in the sensory analysis. The implications of this study for maintaining the quality of free sulfur dioxide white wines are discussed.
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
(2023)
Article
Food Science & Technology
Peizi Sun, Xuedi Zhang, Xiang Ren, Zhiqi Cao, Yanfen Zhao, Hao Man, Dongmei Li
Summary: The effect of basic amino acid (L-arginine, L-lysine, and L-histidine) pretreatment on the quality of canned Antarctic krill was evaluated in this study. It was found that L-lysine pretreatment significantly improved the texture, water-holding capacity, color, and reduced oxidative damage of krill meat. In addition, sensory evaluation indicated that L-lysine-treated canned Antarctic krill had a better flavor and texture compared to other canned products. Overall, L-lysine shows potential as a regulatory strategy for enhancing the quality of canned Antarctic krill.
FOOD AND BIOPROCESS TECHNOLOGY
(2023)
Article
Biochemistry & Molecular Biology
Keisuke Tomohara, Nao Ohashi, Takeru Nose
Article
Multidisciplinary Sciences
Xiaohui Liu, Keitaro Suyama, Takeru Nose, Miki Shimohigashi, Yasuyuki Shimohigashi
Summary: The study reports the dual action of bisphenol compounds on ER alpha and ER beta receptors, with the bisphenol E analogs exhibiting enhanced agonist/antagonist activities due to an electrostatic halogen bond. Bisphenol C (BPC) is found to be a bifunctional ER alpha-agonist and ER beta-antagonist, with high ER alpha activity and inhibitory activity against ER beta. The intensified receptor interaction of BPC is attributed to the presence of an n-pi-pi-n conjugation system mediated through the >C = CCl2 double bond.
Article
Chemistry, Multidisciplinary
Keitaro Suyama, Mika Mawatari, Daiki Tatsubo, Iori Maeda, Takeru Nose
Summary: Elastin and elastin-like peptides (ELPs) are potential base materials for drug-delivery systems and metal-scavenging agents due to their characteristics. Studies have shown that branching ELPs may have advantageous properties in biomaterials compared to their linear counterparts. The multimerization of short ELPs via NTA is a useful strategy to obtain thermoresponsive molecules.
Article
Cell Biology
H. Ongun Onaran, Tommaso Costa
Summary: This review discusses the theoretical and experimental foundations for assessing agonism in GPCRs, emphasizing the importance of separating efficacy from affinity in understanding agonism and identifying ligands with true bias of efficacy for unraveling the conformational space that determines the complex functional chemistry of GPCRs.
CELLULAR SIGNALLING
(2021)
Article
Biochemistry & Molecular Biology
Masaki Iwamoto, Takahiro Masuya, Mari Hosose, Koki Tagawa, Tomoka Ishibashi, Keitaro Suyama, Takeru Nose, Eiji Yoshihara, Michael Downes, Ronald M. Evans, Ayami Matsushima
Summary: Bisphenol derivatives were found to act as coactivator-binding inhibitors (CBIs) affecting ERβ signaling, providing critical insights for future drug development based on ER signaling and revealing their potential as endocrine disruptors.
JOURNAL OF BIOLOGICAL CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Daisuke Asai, Naoko Inoue, Makiko Sugiyama, Tsugumi Fujita, Yutaka Matsuyama, Xiaohui Liu, Ayami Matsushima, Takeru Nose, Tommaso Costa, Yasuyuki Shimohigashi
Summary: This study verifies the importance of the position of benzene hydrogen atoms in activating the receptor, finding that benzene-hydrogen atoms at the ortho and meta positions, rather than the para position, play a crucial role in CH/pi interaction.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Article
Pharmacology & Pharmacy
Biswaranjan Pani, Seungkirl Ahn, Paula K. Rambarat, Shashank Vege, Alem W. Kahsai, Andrew Liu, Bruno N. Valan, Dean P. Staus, Tommaso Costa, Robert J. Lefkowitz
Summary: Carvedilol is a first-choice agent for heart failure treatment with unique pharmacological properties, and compound-6 (cmpd-6) displays exclusive positive cooperativity with carvedilol among other fi-blockers. This cooperative effect enhances the binding affinity of carvedilol for the fi2-adrenergic receptor, potentially improving the efficacy of biased beta blockers and other GPCR therapeutics.
MOLECULAR PHARMACOLOGY
(2021)
Article
Multidisciplinary Sciences
Shogo Sumiyoshi, Keitaro Suyama, Daiki Tatsubo, Naoki Tanaka, Keisuke Tomohara, Suguru Taniguchi, Iori Maeda, Takeru Nose
Summary: In this study, a peptide-based heavy metal scavenging agent was developed by introducing a metal-binding sequence to a short elastin-like peptide (ELP). The agent showed strong self-assembling ability and metal binding affinity, and could be readily recycled by treatment with acidic solution.
SCIENTIFIC REPORTS
(2022)
Article
Biochemistry & Molecular Biology
Keitaro Suyama, Marin Shimizu, Iori Maeda, Takeru Nose
Summary: ELPs, inspired by natural elastin, are thermoresponsive biopolymers ideal for drug delivery carriers. Fn analogs, modified by replacing Phe residues, show significant changes in temperature responsiveness. Aromatic amino acids play important roles in self-assembly of Fn analogs, and the N-terminal residue enhances their self-assembling ability.
Article
Biochemistry & Molecular Biology
Naoki Tanaka, Keitaro Suyama, Keisuke Tomohara, Iori Maeda, Takeru Nose
Summary: Elastin-like peptides (ELPs) exhibit reversible phase transitions triggered by temperature changes, making them useful for various applications. Short ELPs, which can be easily obtained by chemical synthesis, have advantages over long ELPs as they can incorporate different amino acids and affect the temperature-responsive behavior. This study investigated branched short ELP analogs and demonstrated that multimerization of F1 or F2 can obtain molecules capable of coacervation. These temperature-responsive molecules can serve as easy-to-synthesize peptide tags to confer temperature responsiveness to other molecules, aiding the development of temperature-responsive biomaterials.
JOURNAL OF PEPTIDE SCIENCE
(2023)
Article
Multidisciplinary Sciences
Keisuke Tomohara, Nao Ohashi, Tatsuya Uchida, Takeru Nose
Summary: Plant extracts can be used as substrates for chemical engineering to synthesize artificial molecules with natural product-like structures. This method allows for efficient conversion in complex media and exhibits good selectivity and reproducibility. The study also discovered that some of the synthesized molecules exhibit promising inhibitory activity towards protease.
SCIENTIFIC REPORTS
(2022)
Article
Multidisciplinary Sciences
Shogo Sumiyoshi, Keitaro Suyama, Naoki Tanaka, Takumi Andoh, Akihiko Nagata, Keisuke Tomohara, Suguru Taniguchi, Iori Maeda, Takeru Nose
Summary: This study synthesized truncated elastin-like peptide (ELP) analogues by shortening the amino acid sequence and found that the coacervation ability of truncated ELPs is affected by the amino acid sequence rather than the peptide chain length. Among the novel truncated ELP analogues, the 16-mer (FPGV)4 exhibited stronger coacervation ability than the 25-mer (FPGVG)5, and it could also capture Cd2+. These findings suggest that the 16-mer (FPGV)4 composed of proteinogenic amino acids can serve as a new biomaterial with minimal environmental impact.
SCIENTIFIC REPORTS
(2022)
Article
Multidisciplinary Sciences
Keitaro Suyama, Hitoshi Kesamaru, Takashi Okubo, Kazumi Kasatani, Keisuke Tomohara, Ayami Matsushima, Takeru Nose
Summary: Halogenated flame retardants, such as tetrabromobisphenol A (TBBPA), have been found to have adverse effects on human health. However, the risks posed by degraded TBBPA and its derivatives have been largely overlooked. In this study, it was found that degraded TBBPA derivatives exhibited strong cytotoxicity and could induce cell death. Additionally, the growth of Escherichia coli was inhibited in the presence of dehalogenated TBBPA and related compounds. These findings highlight the importance of monitoring the release of halogenated BPA derivatives from flame-retardant-containing products, as they can have adverse effects on human health.
Article
Biochemistry & Molecular Biology
Kohei Yoshida, Keitaro Suyama, Shin Matsushita, Iori Maeda, Takeru Nose
Summary: In this study, efficient preparation of ELPs was investigated using a liquid-phase synthesis method with a hydrophobic benzyl alcohol support (HBA-tag). Short ELPs were successfully obtained in high yield and purity, and their temperature-dependent response was assessed, revealing a reversible phase transition. These findings provide evidence for the potential mass production of ELPs using this approach.
JOURNAL OF PEPTIDE SCIENCE
(2023)