Article
Chemistry, Organic
Lucas Vidal, Pan -Pan Chen, Eva Nicolas, Andrew Hackett, Craig M. Robertson, Kendall N. Houk, Christophe Aissa
Summary: The iridium-catalyzed intramolecular cyclopropanation of alpha-carbonyl sulfoxonium ylides (SY) in the presence of a chiral diene is reported with high yield (up to 96%) and enantioselectivity (98%). Density functional theory calculations suggest that the re face of the olefin prefers to attack an iridium carbene intermediate in an asynchronous concerted step independent of the geometry of the olefin.
Article
Chemistry, Organic
Ming Huang, Changsheng Zhou, Ke-Fang Yang, Ze Li, Guo-Qiao Lai, Pinglu Zhang
Summary: This study developed an effective catalyst for the hydroborylation of cyclopropenes, resulting in the formation of cyclopylboronates that can be transformed into versatile cyclopropanes. This method works under mild reaction conditions in an open-air atmosphere and can be easily scaled up. Control experiments provide key insights into the reaction mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemical Research Methods
Fady Nahra, Nikolaos Tzouras, Alba Collado, Steven P. Nolan
Summary: N-heterocyclic carbene gold(I) chloride and hydroxide complexes are commonly used as synthetic reagents and efficient catalysts. This study describes a straightforward and practical method for synthesizing mononuclear gold complexes with high yields, as well as the synthesis of a mononuclear gold(I) hydroxide complex and an improved synthesis method for a dinuclear gold(I) hydroxide complex. This methodology offers advantages such as the use of sustainable reaction solvents and commercially available starting materials.
Article
Chemistry, Multidisciplinary
David Vesseur, Karinne Miqueu, Didier Bourissou
Summary: A mono-substituted Au(I) carbene was synthesized by reacting HC(N-2)(Dmp) (Dmp = 2,6-dimesitylphenyl) with an (o-carboranyl)-diphosphine AuNTf2 complex. It exhibited stability up to about 10 degrees C and its structure was determined using NMR spectroscopy. Density functional theory calculations revealed that the chelating P<^>P ligand enhanced Au -> C-carb backdonation, while the Dmp substituent provided kinetic stabilization without altering the electronic structure of the carbene complex.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Ichraf Slimani, Serap Sahin-Bolukbasi, Mustafa Ulu, Enes Evren, Nevin Gurbuz, Ilknur Ozdemir, Naceur Hamdi, Ismail Ozdemir
Summary: A series of rhodium(i) complexes with N-heterocyclic carbene ligands showed high in vitro cytotoxic activity against human cancer cells, with complex 2b exhibiting the most selective cytotoxic activity. These complexes demonstrated greater cytotoxicity against cancer cells compared to established anticancer agents cisplatin and 5-fluorouracil.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Zita Szabo, Sophia Ben Ahmed, Zoltan Nagy, Attila Paczal, Andras Kotschy
Summary: The formation of polysubstituted cyclopropane derivatives in the gold(I)-catalyzed reaction of olefins and propargylic esters is of significant interest due to its potential usefulness in generating diversity. We tested a series of chiral gold(I)-carbene complexes as catalysts and achieved high enantioselectivity in the test reaction. However, the cis:trans selectivity of the transformation was independent of the catalyst. Although the reactions proceeded smoothly, the observed enantioselectivity varied greatly and a structure-property relationship could not be established.
Article
Chemistry, Inorganic & Nuclear
Clemens Kaussler, Darren Wragg, Claudia Schmidt, Guillermo Moreno-Alcantar, Christian Jandl, Johannes Stephan, Roland A. Fischer, Stefano Leoni, Angela Casini, Riccardo Bonsignore
Summary: This study focuses on improving the design of metal complexes as stabilizers of noncanonical DNA secondary structures. A series of cyclic dinuclear Au(I) N-heterocyclic carbene complexes based on xanthine and benzimidazole ligands have been synthesized and characterized. The compounds show stabilization properties towards G-quadruplexes (G4s) and moderate antiproliferative activity in human cancer cells. The binding modes and free energy landscape of the most active compound have been studied using metadynamics.
INORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Lauriane C. Peyrical, Marie-Rose Ouellet-Du Berger, Maxim Boucher, Melodie Birepinte, Jean-Francois Paquin, Andre B. Charette
Summary: Trifluoromethyl (CF3) and pentafluorosulfanyl (SF5) substituted cyclopropane-fused gamma-lactones were successfully synthesized through Rh2(esp)2-catalyzed intramolecular cyclopropanation, with yields up to 99%. Twelve examples of this interesting scaffold are reported, along with postfunctionalizations to access highly functionalized CF3- and SF5- substituted cyclopropanes. These novel SF5-substituted analogues join the limited list of available pentafluorosulfanyl intermediates.
Review
Chemistry, Multidisciplinary
Tingting Li, Zhichao Jin, Yonggui Robin Chi
Summary: This review discusses N-heterocyclic carbene-catalyzed reactions for the formation of aromatic compounds, categorizing them into 4 types based on activation modes. The achievements, challenges, and future research directions in NHC-catalyzed arene construction processes are summarized. The outlook is based on the authors' opinions and knowledge on the trends of NHC organocatalysis development.
SCIENCE CHINA-CHEMISTRY
(2022)
Article
Chemistry, Applied
Andrea Longhi, Marco Baron, Marzio Rancan, Gregorio Bottaro, Laura Orian, Claudia Graiff, Marco Roverso, Ileana Menegazzo, Lidia Armelao, Sara Bogialli, Cristina Tubaro
Summary: This study explored the coordinating properties of the bis(1,4-dimethyl-1,2,4-triazol-5-ylidene) ligand (bitz) towards silver(I) and gold(I) centers. Results showed that bitz behaves as a bridging ligand, forming both dinuclear and trinuclear complexes, which were supported by X-ray diffraction analysis, NMR spectroscopy, and mass spectrometry evidence.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Kun-Quan Chen, He Sheng, Qiang Liu, Pan-Lin Shao, Xiang-Yu Chen
Summary: In recent years, NHC-catalyzed radical reactions have been gaining attention for their potential to create new activation modes previously inaccessible. Further research and understanding of this emerging area is warranted to explore its synthetic techniques and advantages.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Chemistry, Inorganic & Nuclear
Pokpong Rungthanaphatsophon, Alexander J. Gremillion, Yuzhong Wang, Steven P. Kelley, Gregory H. Robinson, Justin R. Walensky
Summary: N-Heterocyclic Carbene (NHC) ligands play a crucial role in synthesizing novel metal and main group-containing compounds. This study focuses on the coordination chemistry of CS2 and PhNCS derivatives of the sterically encumbering 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene (IPr).
INORGANICA CHIMICA ACTA
(2021)
Article
Chemistry, Multidisciplinary
Zhi-Xiu Rao, Pei-Bo Chen, Jin Xu, Qing Wang, Hai-Tao Tang, Ying Liang, Ying-Ming Pan
Summary: A copper-based N-heterocyclic carbene porous polymer catalyst (Cu@NHC-1) was successfully fabricated for the direct conversion of low concentration CO2 into oxazolidinones. Cu@NHC-1 shows highly efficient and selective adsorption, activation, and conversion of the low concentration CO2 due to its porous structure, nitrogen activation sites, and catalytic Cu center. The practical application potential of Cu@NHC-1 was demonstrated by successfully converting CO2 in lime kiln waste gas into oxazolidinones under mild conditions.
Article
Chemistry, Multidisciplinary
Zhi-Xiu Rao, Pei-Bo Chen, Jin Xu, Qing Wang, Hai-Tao Tang, Ying Liang, Ying-Ming Pan
Summary: Copper-based N-heterocyclic carbene porous polymer catalyst (Cu@NHC-1) was successfully fabricated for the direct conversion of low concentration CO2 into oxazolidinones. Cu@NHC-1 exhibited high efficiency and selectivity in adsorption, activation, and conversion of the low concentration CO2 (30 vol %) due to its porous structure, nitrogen activation sites, and catalytic Cu center. It was able to convert CO2 in lime kiln waste gas into oxazolidinones in satisfactory yields under mild conditions.
Review
Biochemistry & Molecular Biology
Kuiyong Dong, Mengting Liu, Xinfang Xu
Summary: This review summarizes the applications of copper as a catalyst in synthetic chemistry and catalysis. It focuses on the reactions between copper carbene intermediates and alkyne species. Two different reaction models are discussed, highlighting the practicality and mildness of these methods.
Review
Biochemistry & Molecular Biology
John K. Everett, Roberto Tejero, Sarath B. K. Murthy, Thomas B. Acton, James M. Aramini, Michael C. Baran, Jordi Benach, John R. Cort, Alexander Eletsky, Farhad Forouhar, Rongjin Guan, Alexandre P. Kuzin, Hsiau-Wei Lee, Gaohua Liu, Rajeswari Mani, Binchen Mao, Jeffrey L. Mills, Alexander F. Montelione, Kari Pederson, Robert Powers, Theresa Ramelot, Paolo Rossi, Jayaraman Seetharaman, David Snyder, G. V. T. Swapna, Sergey M. Vorobiev, Yibing Wu, Rong Xiao, Yunhuang Yang, Cheryl H. Arrowsmith, John F. Hunt, Michael A. Kennedy, James H. Prestegard, Thomas Szyperski, Liang Tong, Gaetano T. Montelione
Article
Biochemistry & Molecular Biology
Jeffrey L. Mills, Gaohua Liu, Arne Skerra, Thomas Szyperski
Article
Chemistry, Multidisciplinary
Bryan S. Der, Mischa Machius, Michael J. Miley, Jeffrey L. Mills, Thomas Szyperski, Brian Kuhlman
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2012)
Article
Biochemistry & Molecular Biology
Kiran Kumar Singarapu, Jeffrey L. Mills, Rong Xiao, Thomas Acton, Marco Punta, Markus Fischer, Barry Honig, Burkhard Rost, Gaetano T. Montelione, Thomas Szyperski
PROTEINS-STRUCTURE FUNCTION AND BIOINFORMATICS
(2010)
Article
Biochemistry & Molecular Biology
Grant S. Murphy, Jeffrey L. Mills, Michael J. Miley, Mischa Machius, Thomas Szyperski, Brian Kuhlman
Article
Cell Biology
Qingzhong Kong, Jeffrey L. Mills, Bishwajit Kundu, Xinyi Li, Liuting Qing, Krystyna Surewicz, Ignazio Cali, Shenghai Huang, Mengjie Zheng, Wieslaw Swietnicki, Frank D. Sonnichsen, Pierluigi Gambetti, Witold K. Surewicz
Article
Biochemistry & Molecular Biology
Brianne M. Dudiak, Kenneth R. Maksimchuk, Maria M. Bednar, Christopher J. Podracky, Jonathan M. Burg, Tri M. Nguyen, Felix O. Nwogbo, Raphael H. Valdivia, Dewey G. McCafferty
Article
Microbiology
Tri Nguyen, Sohyoung Lee, Yi-An Yang, Changhwan Ahn, Ji Hyun Sim, Tiffany G. Kei, Karen N. Barnard, Hai Yu, Shawn K. Millano, Xi Chen, Colin R. Parrish, Jeongmin Song
Article
Microbiology
Sohyoung Lee, Yi-An Yang, Shawn K. Milano, Tri Nguyen, Changhwan Ahn, Ji Hyun Sim, Andrew J. Thompson, Eric C. Hillpot, Gyeongshik Yoo, James C. Paulson, Jeongmin Song
CELL HOST & MICROBE
(2020)
Article
Multidisciplinary Sciences
Changhwan Ahn, Yi-An Yang, Durga P. Neupane, Tri Nguyen, Angelene F. Richards, Ji Hyun Sim, Nicholas J. Mantis, Jeongmin Song
Summary: The study demonstrates that antibiotic-resistant S. Typhi continuously secretes typhoid toxin during infection, and identifies toxin-neutralizing antibodies targeting specific components of the toxin. These findings offer critical insights into strategies for neutralizing typhoid toxin.
Article
Cell Biology
Ankur H. Shah, Nicholas L. Cianciola, Jeffrey L. Mills, Frank D. Soennichsen, Cathleen Carlin
JOURNAL OF CELL BIOLOGY
(2007)
Article
Biophysics
T Szyperski, JL Mills, D Perl, J Balbach
EUROPEAN BIOPHYSICS JOURNAL WITH BIOPHYSICS LETTERS
(2006)
Article
Biochemistry & Molecular Biology
JM Aramini, JL Mills, R Xiao, TB Acton, MJ Wu, T Szyperski, GT Montelione
JOURNAL OF BIOMOLECULAR NMR
(2003)
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)