Article
Chemistry, Multidisciplinary
Guoxiu Wang, Wenjuan Lv, Congjie Pan, Hongli Chen, Xingguo Chen
Summary: A novel chiral COF, DA-TD COF, was synthesized and used as a chiral stationary phase for open-tubular capillary electrochromatography, showing excellent enantioseparation efficiency and stability. The enantioseparation mechanism was also studied in this work.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Medicinal
Rada Bunthawong, Uthaiwan Sirion, Arthit Chairoungdua, Kanoknetr Suksen, Pawinee Piyachaturawat, Apichart Suksamrarn, Rungnapha Saeeng
Summary: Two new series of andrographolide analogues were designed and synthesized from natural andrographolide, showing different cytotoxicity against cancer cells. Compounds with formyl group exhibited selective activity on P-388 cell line. Computational studies revealed the importance of specific functional groups in cytotoxicity.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Physical
Sumit S. Bhawal, Puthusserickal A. Hassan, Santosh L. Gawali, Sandeep R. Patil, Vishal N. Patil, Shehnaz H. Solanki, Dhana Lakshmi Manyala, Dharmesh S. Varade
Summary: In this study, the synthesis and interfacial properties of choline cholate (CC) and choline deoxy cholate (CDC) surfactants prepared through salt metathesis reaction were reported. The experiments showed that both CC and CDC formed well-defined micelles and exhibited good foamability in the presence of CTAB. The findings of this study are of great importance for the formulation design of pharmaceutical and personal care products.
JOURNAL OF MOLECULAR LIQUIDS
(2022)
Article
Chemistry, Multidisciplinary
Zeshi Li, Luca Unione, Lin Liu, Yifei Lang, Robert P. de Vries, Raoul J. de Groot, Geert-Jan Boons
Summary: O-acetylation of sialic acids plays a role in various coronaviruses and influenza viruses, but different viruses exhibit distinct requirements for O-acetylation, and ester-to-amide perturbation can result in decreased or loss of binding. Molecular modeling studies suggest that binding specificity is governed by the complementarity between acetyl moieties of sialosides and hydrophobic patches of the lectin.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Martin Jaeger Pedersen, Christian Marcus Pedersen
Summary: A method for introducing dimethylphenylsilyl at the 4-position in carbohydrates has been developed, showing higher reactivity compared to the corresponding 4-deoxy-analogue. The introduction of a C-Si increases the relative reactivity by a modest factor of around two.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Olga Michalak, Marcin Cybulski, Wojciech Szymanowski, Agnieszka Gornowicz, Marek Kubiszewski, Kinga Ostrowska, Piotr Krzeczynski, Krzysztof Bielawski, Bartosz Trzaskowski, Anna Bielawska
Summary: A series of new derivatives of ursolic acid (UA) were designed and synthesized by substituting various amino acids (AAs) or dipeptides (DP) at the C-3 position of the steroid skeleton. These conjugates exhibited cytotoxic activity against hormone-dependent and triple-negative breast cancer cells. Mechanistic studies revealed the activation of apoptotic pathways for some compounds and the induction of autophagy for others. Additionally, the synthesized compounds showed potential as anticancer agents based on their ADME properties and molecular docking to the estrogen receptor.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Organic
Piotr Dudzinski, Wibke S. Husstedt, Andrej Matsnev, Joseph S. Thrasher, Guenter Haufe
Summary: The steric hindrance of the SF5 group hindered the [3,3]-sigmatropic rearrangement reactions. The use of 1-SF5-alk-1-en-3-ols failed to successfully incorporate the 1-SF5-substituted 1,2-double bond in Johnson-Claisen, ester enolate-Claisen, and Ireland-Claisen rearrangements.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Yuling Mei, Nan Jiang, Yu Yang, Wan Zhang, Saifeng Qiu, Hong Guo, Jianbo Zhang
Summary: A convenient protocol for the beta-stereoselective synthesis of 2-deoxy- C -arylglycosides has been developed, involving one-step reaction using I (2) /Et (3) SiH. The approach is applicable to a wide range of naphthol moieties and was demonstrated to be effective in the synthesis of 5-aza analogues of aquayamycin.
Article
Biochemistry & Molecular Biology
Urszula Bachor, Agnieszka Lizak, Remigiusz Bachor, Marcin Maczynski
Summary: Hybrid peptides composed of alpha and beta-amino acids have potential as therapeutic agents. Therefore, the development of new unnatural amino acids and methods for their incorporation is important. In this study, we investigated the application of 5-amino-3-methyl-isoxazole-4-carboxylic acid (AMIA) in solid phase peptide synthesis. The results show that this unnatural beta-amino acid can be used in synthesizing a new class of bioactive peptides.
Article
Chemistry, Multidisciplinary
Yixuan Zhou, Kuo-Shiang Liao, Shiou-Ting Li, Chung-Yi Wu
Summary: This article presents a facile and scalable route for synthesizing di-azido sugars and explores the dependency pattern between solvent and protecting groups. It also introduces a chemical synthetic strategy for pseudaminic acid precursors and discusses the configuration of nonulosonic acid precursors.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Michael K. F. Mohr, Raspudin Saleem-Batcha, Nicolas V. Cornelissen, Jennifer N. Andexer
Summary: Chemical modification of small molecules is crucial for pharmaceutical development, and S-adenosyl-L-methionine (SAM) analogues are used by methyltransferases (MTs) for selective derivatisation of various molecules. There is a need for l-methionine analogues for the synthesis of SAM analogues, which are mostly unavailable commercially. In this study, we investigated the substrate scope of ScOAHS from Saccharomyces cerevisiae for the production of l-methionine analogues, and successfully synthesized nine different analogues with modifications on the thioether residue. Combining ScOAHS with an established MT-dependent three-enzyme alkylation cascade further enhanced the conversion rate, indicating the beneficial effect of in situ production of l-methionine analogues.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Yanzhi Zhang, Yibo Wang, Guangjun Xie, Junyang Chen, Ankang Hu, Runmei Wang, Tianchen He, Dilawo Duolikun, Haiying Sun
Summary: Efficient methods for synthesizing three dipeptide mimetics with diazabicycloalkanone amino acid scaffolds were developed, with compound 3 serving as a key intermediate for a clinical staged IAP inhibitor. Compared to reported methods, the new method is more efficient and suitable for large scale preparation.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Mickey Vinodh, Fatemeh H. Alipour, Talal F. Al-Azemi
Summary: Urea-functionalized anion receptors based on brominated functionalized pillar[5]arenes were synthesized and their binding affinity towards halide anions was investigated using 1H NMR titration and isothermal titration calorimetry (ITC). The structure of the receptor and the nature of the anionic guest affected the complexation behavior, with the synthesized receptors showing high selectivity towards fluoride and forming a 1:2 host-to-guest complex. The anion receptor based on the 1,3-alternate pillar[5]arene regioisomer exhibited the highest affinity towards fluorine anions, while no significant interactions were observed with larger bromine anions. Diffusion-ordered spectroscopy (DOSY), ITC, and dynamic light scattering (DLS) measurements demonstrated the formation of a self-assembled supramolecular polymer driven by hydrogen bonds in solution.
Article
Chemistry, Multidisciplinary
Farhad Sedighi Pashaki, Mohammad Nikpassand
Summary: Fe3O4@SiO2@Tannic acid was used as a catalyst to successfully synthesize high-yield 5-amino-pyrazole-4-carbonitrile compounds with short reaction times and easy recyclability for multiple cycles. These structures were confirmed by H-1 NMR, C-13 NMR, FTIR spectra, and elemental analyses.
FRONTIERS IN CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Hongquan Zhang, Chunxi Wen, Bingting Li, Xinlin Yan, Yangrong Xu, Jialin Guo, Shi Hou, Jiajia Chang, Song Li, Junhai Xiao
Summary: Radiotherapy is an essential treatment for brain tumors, but radioresistance caused by the non-sensitivity of tumor cells in hypoxic areas can reduce its effectiveness. This study designed and synthesized novel compounds that increase the oxygen concentration within tumors to enhance the sensitivity to radiation. In vitro experiments demonstrated that certain compounds effectively improved oxygen-releasing properties compared to the positive control, and safety evaluation indicated their low cytotoxicity. Furthermore, animal studies confirmed the radiosensitization effect of one compound on orthotopically transplanted glioblastoma.
Article
Chemistry, Organic
Daniel Wiegmann, Anatol P. Spork, Giuliana Niro, Christian Ducho
Article
Microbiology
Zheng Cui, Xia-Chang Wang, Xiaodong Liu, Anke Lemke, Stefan Koppermann, Christian Ducho, Jorgen Rohr, Jon S. Thorson, Steven G. van Lanen
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY
(2018)
Article
Chemistry, Medicinal
Lina Y. El-Sharkawy, Rowaida A. El-Sakhawy, Mohammad Abdel-Halim, Kevin Lee, Gary A. Piazza, Christian Ducho, Rolf W. Hartmann, Ashraf H. Abadi
ARCHIV DER PHARMAZIE
(2018)
Article
Chemistry, Organic
Ruth Linder, Christian Ducho
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Kristin Leyerer, Stefan Koppermann, Christian Ducho
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Biochemistry & Molecular Biology
Anna Heib, Giuliana Niro, Stefanie C. Weck, Stefan Koppermann, Christian Ducho
Article
Biochemical Research Methods
Abed Saady, Melissa Wojtyniak, Eli Varon, Verena Boettner, Noa Kinor, Yaron Shav-Tal, Christian Ducho, Bilha Fischer
BIOCONJUGATE CHEMISTRY
(2020)
Article
Biochemistry & Molecular Biology
Melissa Wojtyniak, Boris Schmidtgall, Philine Kirsch, Christian Ducho
Article
Chemistry, Multidisciplinary
Giuliana Niro, Stefanie C. Weck, Christian Ducho
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Review
Biochemistry & Molecular Biology
Manuel Hawner, Christian Ducho
Article
Chemistry, Medicinal
Katrin Voos, Esther Schoenauer, Alaa Alhayek, Joerg Haupenthal, Anastasia Andreas, Rolf Mueller, Rolf W. Hartmann, Hans Brandstetter, Anna K. H. Hirsch, Christian Ducho
Summary: Microbial infections pose a significant threat to public health, and the rise in resistance calls for urgently needed new antibiotics. The zinc metalloprotease collagenase H (ColH) from Clostridium histolyticum is a virulence factor that catalyses tissue damage, making it an attractive target for new antivirulence agents. A phosphonate motif as a zinc-binding group showed promising activity against ColH, improved selectivity, and higher stability, making it a promising candidate for future drug development.
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
Chemistry, Medicinal
Reem K. Fathalla, Matthias Engel, Christian Ducho
Summary: 8-Anilinonaphthalene-1-sulfonic acid (ANS) is a fluorescent probe commonly used to detect conformational changes in proteins. This study discovered that ANS can inhibit the activity of various isoforms of MurA and identified a more potent ANS analog. These findings highlight the potential of targeting the ANS binding pocket for the development of antibiotics.
ARCHIV DER PHARMAZIE
(2023)
Article
Chemistry, Organic
Kristin Leyerer, Stefan Koppermann, Christian Ducho
Article
Chemistry, Multidisciplinary
Boris Schmidtgall, Arne Kuepper, Melissa Meng, Tom N. Grossmann, Christian Ducho
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
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)
