Article
Chemistry, Multidisciplinary
Shibing Zheng, Dongjie Shi, Tianjiang Sun, Letian Zhang, Weijia Zhang, Yixin Li, Zhenbo Guo, Zhanliang Tao, Jun Chen
Summary: In this study, a hydrogen bond network (HBN) was proposed to suppress the solubility of high-capacity small organic materials. The H-bond formation between H and O in PTO-NH2 molecule resulted in a transverse two-dimensional extension and longitudinal pi-pi stacking structure. The HBN structure enhanced active site utilization, cycle stability, and rate performance of PTO-NH2.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Applied
Shuhan Feng, Jianyong Yi, Youchuan Ma, Jinfeng Bi
Summary: The morphology of ice crystals in amidated pectin gels with different crosslink strengths was investigated. Increasing the degree of amidation resulted in shorter homogalacturonan regions in pectin chains. Highly amidated pectin formed a faster gelation rate and a stronger gel micro-network through hydrogen bonds. Lower degree of amidation led to the formation of smaller ice crystals in frozen gels, indicating that a weaker cross-linked gel micro-network effectively inhibited crystallization. Lyophilized gel scaffolds with high crosslink strength displayed fewer pores, high porosity, lower specific surface area, and greater mechanical strength after sublimation. The study suggests that the microstructure and mechanical properties of freeze-dried pectin porous materials can be controlled by adjusting the crosslink strength of pectin chains through amidation in the homogalacturonan regions.
Article
Chemistry, Multidisciplinary
Daniel A. Decato, Asia Marie S. Riel, James H. May, Vyacheslav S. Bryantsev, Orion B. Berryman
Summary: This paper experimentally quantifies a Hydrogen Bond-Enhanced Halogen Bond (HBeXB) for the first time, showing that electron-rich halogen bond donors are strengthened most by an adjacent hydrogen bond, and stronger hydrogen bond donors enhance the halogen bond the most. X-ray crystal structures and F-19 NMR titrations support the findings, laying the foundation for future studies on hydrogen bonds and halogen bonds in close proximity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Sihao Li, Caimei Gong, Yuyang Zhang, Shizhang Fu, Zhongping Wang, Yan Lu, Siyi Gu, Xiaoqing Liu, Li Wang
Summary: The modulation effects of Cu2+/Fe3+ ions on the hydrogen-bonded structure of TATB on a HOPG surface have been investigated. The self-assembled structures of TATB molecules formed by metal-ligand coordination bonds can be effectively adjusted by regulating the concentration of metal ions in a mixed solution, leading to the diversity of molecular architectures dominated by coordination bonds.
Article
Biochemistry & Molecular Biology
Laura J. J. Voigt, Katie E. E. Tucker, Paul M. M. Zelisko
Summary: In this work, the natural hydrogen bonding capacity of thymine was used to produce silicone polymer systems that can be cross-linked by hydrogen bonds. These thymine-modified polymers displayed thermal absorptions and releases, indicative of bond breaking and reformation, and showed the ability to be recycled and remolded through heating and cooling.
Article
Chemistry, Multidisciplinary
Wenqi Hu, Hexu Zhang, Peng Cheng, Lan Chen, Zhi Chen, Svetlana Klyatskaya, Mario Ruben, Johannes V. Barth, Kehui Wu, Yi-Qi Zhang
Summary: By combining surface-confined reactions with supramolecular self-assembly, simple molecular precursors can be transformed into higher-level tectons to generate complex tessellations with unique properties. Using low-temperature scanning tunneling microscopy, efficient chemical reactions converting EP precursors into BPE-Ag complexes were confirmed, leading to the formation of three distinct types of nanoporous supramolecular architectures with BPE-Ag dimers as the basic units.
Article
Chemistry, Multidisciplinary
Li Chen, Jingshuang Dang, Juan Du, Changwei Wang, Yirong Mo
Summary: Recent research has explored the sensitivity of intrinsic bond strengths to external electric fields (EEFs) by examining noncovalent bonds. It was found that X-bonds primarily responded to EEFs due to changes in covalency, while H-bonds were mainly influenced by steric effects. Additionally, X-bonds were more sensitive to EEFs compared to H-bonds, with the key difference lying in charge transfer interactions. Phenylboronic acid was studied as a smart linker in EEFs, demonstrating switchable sensitivity in response to EEFs.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Multidisciplinary
Vijayanath Elakkat, Eskedar Tessema, Chia-Her Lin, Xiaoping Wang, Huan-Cheng Chang, You-Ning Zheng, Yu-Cheng Huang, Zhong-Yun Gurumallappa, Zhong-Yun Zhang, Ka Long A. Chan, Hening A. S. Rahayu, Joseph S. Francisco, Norman Lu
Summary: To understand the effect of non-covalent weak interactions on molecules, we investigated different types of weak interactions in fluorinated chiral zinc complexes, including improper H-bonding, tetrel bonds, and halogen bonds. High resolution neutron diffraction studies revealed elongation and shortening of the methylene carbon-hydrogen bond due to tetrel bonds and improper H-bond interactions, respectively. We demonstrated how multiple weak interactions can cumulatively affect the C-H bond and offset its elongation through formation of an improper H-bond. Non-covalent interaction and electrostatic potential analysis investigations confirmed the nature of these interactions using density functional theory (DFT) and related calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Materials Science, Ceramics
Mohammad Rasoul Javadi Sigaroodi, Esmaeil Poursaeidi, Javad Rahimi, Yousef Yousefi Jamalabad
Summary: The effect of heat treatment, growth of TGO layer, oxidation of bond coat, and the presence of two bond coats on the thermal shock resistance of TBC were investigated experimentally. TGO oxide layers were created through two-time heat treatment, and thermal shock tests were performed on samples with different bond coat configurations. The results showed that the use of two bond coats and a thin TGO layer had a positive effect on TBC performance. The presence of two bond coats increased the shock resistance by an average of 37.2%. 12-hour heat treatment led to a 14.0% and 17.4% increase in shock resistance for samples with HVOF/APS/APS layer and APS/APS layer, respectively. 24-hour heat treatment decreased the performance of samples with two bond coats and one bond coat by 6.7% and 10.2%, respectively.
JOURNAL OF THE EUROPEAN CERAMIC SOCIETY
(2023)
Review
Polymer Science
Hui-Qing Peng, Wenping Zhu, Wu-Jie Guo, Qingyun Li, Shixiang Ma, Christophe Bucher, Bin Liu, Xiaofan Ji, Feihe Huang, Jonathan L. Sessler
Summary: Supramolecular polymers are self-assembled structures formed through noncovalent interactions, exhibiting reversibility, responsiveness, and stability. They have diverse applications in various fields. This review focuses on the determinants and driving forces of supramolecular polymer construction, highlighting the influence of different noncovalent interactions on their structure and function. Understanding these connections contributes to further advancements in this field.
PROGRESS IN POLYMER SCIENCE
(2023)
Article
Chemistry, Physical
Andre Nicolai Petelski, Silvana Carina Pamies, Maria Josefina Veronica Marquez, Gladis Laura Sosa, Nelida Maria Peruchena
Summary: This study computationally investigates how to improve the binding strength of melamine (M) supramolecules through covalent modifications. The research provides molecular tools for the rational design of emerging materials based on uneven hydrogen-bonded arrangements.
Article
Chemistry, Multidisciplinary
Eva Korytiakova, Ewelina Kaminska, Markus Mueller, Thomas Carell
Summary: The synthesis of a fluorinated fdC feeding probe allowed for the study of direct deformylation to F-dC, providing insights into the Tdg-independent removal process. The research demonstrated deformylation occurring in both stem cells and different somatic cell types. Additionally, active demethylation was investigated in a non-dividing neurogenin-inducible system of iPS cells differentiating into bipolar neurons.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Andrey V. Marchenko, Valery A. Ozeryanskii, Oleg P. Demidov, Alexander S. Antonov, Elena Yu. Tupikina, Alexander F. Pozharskii
Summary: The lithiation reaction of 2,7-disubstituted derivatives of 1,8-bis(dimethylamino)naphthalene (DMAN) bearing OMe, NMe2, and SMe groups was studied. It was found that OMe groups facilitate the selective dual beta-lithiation of the naphthalene moiety, while NMe2 groups allow only monolithiation due to decreased acidity and conformational immobilization. SMe groups do not undergo ring lithiation but undergo deprotonation. The synthesis of previously unknown 2,3,6,7-tetrasubstituted DMANs was achieved, providing the first opportunity to study the double buttressing effect (BE) version.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Marjan Sebghati, Atekeh Tarahhomi, Marjan Sadat Bozorgvar, Dan G. Dumitrescu, Arie van der Lee
Summary: The study investigated the crystalline forms of tris(pyridin-2-yl)phosphoric triamide both as a metal complex and purely organic pseudopolymorphs. Compound 1 represents a unique example of a chelate phosphoric triamide complex.
Article
Chemistry, Multidisciplinary
Chang-Qiu Guo, Chuan-Jun Lu, Li-Wen Zhan, Peng Zhang, Qi Xu, Jia Feng, Ren-Rong Liu
Summary: This study reports a new catalyst that successfully catalyzes the enantioselective coupling reaction between quinone esters and anilines, resulting in the formation of N-aryl quinone atropisomers with a unique intramolecular hydrogen bond. This method has the potential to be used for the synthesis of structurally diverse secondary amine atropisomers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Pharmacology & Pharmacy
Pedro Azalim, Fernando M. do Monte, Mariana Manzano Rendeiro, Xiaofan Liu, George A. O'Doherty, Carlos Frederico Fontes, Suzana Guimaraes Leitao, Luis Eduardo M. Quintas, Francois Noel
BIOCHEMICAL PHARMACOLOGY
(2020)
Article
Chemistry, Organic
Sugyeom Kim, Yu Li, Lin Lin, Peyton R. Sayasith, Ariel T. Tarr, Eric B. Wright, Sharia Yasmin, Deborah A. Lannigan, George A. O'Doherty
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Yu Li, Zachary M. Sandusky, Rajender Vemula, Qi Zhang, Bulan Wu, Shinji Fukuda, Mingzong Li, Deborah A. Lannigan, George A. O'Doherty
Review
Medical Laboratory Technology
Thea Brennan-Krohn, Roman Manetsch, George A. O'Doherty, James E. Kirby
TRANSLATIONAL RESEARCH
(2020)
Article
Chemistry, Multidisciplinary
Ehesan U. Sharif, Pei Shi, George A. O'Doherty
Summary: Two unnatural regioisomeric glycosylated Gilvocarcin analogues were proposed as model compounds to study the biosynthetic origin of Gilvocarcins and the proposed O- to C-glycoside migration in the evolution of Angucycline antibiotics. The analogue with weak antibiotic activity compared to Gilvocarcin M was synthesized using a regio-divergent synthetic pathway with a Mitsunobu-like invertive cyclictolization reaction to install the carbasugar motif.
ISRAEL JOURNAL OF CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Jessica Martins de Moura Valadares, Sumit O. Bajaj, Hongyan Li, Hua-Yu L. Wang, Simone Cavalcante Silva, Israel Jose Pereira Garcia, Duane Gischewiski Pereira, Pedro Azalim, Luis Eduardo Menezes Quintas, Francois Noel, Vanessa Faria Cortes, George Augustine O'Doherty, Leandro Augusto Barbosa
Summary: This study assessed the cytotoxic potential of novel digitoxigenin derivatives in cancer cells, showing higher cytotoxicity and selectivity in tumor cells compared to non-tumor cells. The derivatives were also found to modulate specific ATPases in a manner that suggests their importance in the cytotoxic effect on cancer cells.
JOURNAL OF CELLULAR BIOCHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Caitlyn L. Mills, Pengcheng Yin, Becky Leifer, Lori Ferrins, George A. O'Doherty, Penny J. Beuning, Mary Jo Ondrechen
Summary: This study investigates the functional characterization of eight structural genomics proteins from the Crotonase superfamily and uses the SALSA method for functional annotation. It is found that most of these proteins exhibit hydrolase activity in addition to their expected enoyl CoA hydratase activity.
ACS CHEMICAL BIOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Karol R. Francisco, Yu Li, Brent Lindquist-Kleissler, Jiamin Zheng, Yalan Xing, George A. O'Doherty
Summary: A one pot alkylative carboxylation reaction of 2-acetylfuran was developed for the synthesis of methyl beta-ketoesters. The beta-keto-ester product was used for the asymmetric synthesis of a C-7 pyranone precursor for a Pd-glycosylation reaction, with the ultimate goal of synthesizing natural products containing pyran rings, such as Aspergillide C.
JOURNAL OF CO2 UTILIZATION
(2021)
Article
Chemistry, Organic
Yanping Wang, George A. O'Doherty
Summary: An asymmetric approach for the total synthesis of the polyketide natural product EBC-23 is reported, involving a convergent strategy and a late-stage Claisen-like enolate/acid chloride coupling. The key 1,3-diketone intermediate was successfully established, and further transformations led to the synthesis of EBC-23.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Lisa Ngu, Debarpita Ray, Samantha S. Watson, Penny J. Beuning, Mary Jo Ondrechen, George A. O'Doherty
Summary: A diastereoselective synthesis of the beta-anomer of glycinamide ribonucleotide (beta-GAR) has been developed with a high overall yield. The synthetic beta-GAR demonstrated remarkable resistance to anomerization in both solution and solid state.
Article
Chemistry, Multidisciplinary
Yalan Xing, George A. O'Doherty
Summary: An asymmetric approach for synthesizing aspergillide-C has been developed, using asymmetric Noyori transfer hydrogenations to prepare the key fragments and establishing their absolute stereochemistry. The fragments were then coupled using a specific catalyzed reaction to form a protected variant of aspergillide-C.
Review
Chemistry, Multidisciplinary
Sugyeom Kim, Jeremy Oiler, Yalan Xing, George A. O'Doherty
Summary: The development and application of asymmetric synthesis of oligosaccharides from achiral starting materials are reviewed in this article. This approach involves the use of asymmetric catalysis to synthesize optically pure furan alcohols, in combination with Achmatowicz oxidative rearrangement for the synthesis of various pyranones. Additionally, diastereoselective palladium-catalyzed glycosylation and subsequent diastereoselective post-glycosylation transformation are used for the synthesis of oligosaccharides.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Yuzhi Ma, Rajender Vemula, Qi Zhang, Bulan Wu, George A. O'Doherty
Summary: The full account of a de novo asymmetric total synthesis of (+)-monanchorin, a guanidine alkaloid natural product, has been reported. The optimized synthesis route enables the access to both enantiomers of the compound in nine steps starting from the commodity chemicals furan and caproic acid. The synthesis relied on various reactions, including asymmetric Noyori hydrogen transfer reduction, Achmatowicz rearrangement, diastereoselective palladium-catalyzed glycosylation, reductive amination, and acid-catalyzed bicyclic guanidine mixed acetal formation.
GREEN SYNTHESIS AND CATALYSIS
(2022)
Article
Biochemistry & Molecular Biology
Eric B. Wright, Shinji Fukuda, Mingzong Li, Yu Li, George A. O'Doherty, Deborah A. Lannigan
Summary: The study identified a natural product, SL0101, that binds specifically to RSK1/2 by inducing conformational rearrangement, but not to RSK3/4 due to a single amino acid difference. Kinetic analysis revealed that regions outside of the N-terminal kinase domain also contribute to stable inhibitor binding towards RSK2. Additionally, a modification on SL0101 was discovered to form a highly stable inhibitor complex with RSK2, suggesting potential for identifying RSK2-specific inhibitors.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Matthew Tcheng, Vitor L. S. Cunha, Nawaz Ahmed, Xiaofan Liu, Richard W. Smith, Kevin A. Rea, Tariq A. Akhtar, Angelo D'Alessandro, Mark D. Minden, Jerry Vockley, George A. O'Doherty, Todd L. Lowary, Paul A. Spagnuolo
Summary: This study conducted a structure-activity analysis on avocadyne, identifying specific structural features critical to suppressing mitochondrial fatty acid oxidation.