Article
Chemistry, Multidisciplinary
Xin He, Pengchen Ma, Yuhai Tang, Jing Li, Shenyu Shen, Martin J. Lear, K. N. Houk, Silong Xu
Summary: We report a phosphine-catalyzed (3 + 2) annulation of cyclopropenones with various electrophilic pi systems, yielding products including butenolides, butyrolactams, maleimides, and iminomaleimides in high yields with a wide range of substrates. An alpha-ketenyl phosphorous ylide is identified as the key intermediate, which undergoes preferential catalytic cyclization with aldehydes. This phosphine-catalyzed activation of cyclopropenones provides a versatile C-3 synthon for formal cycloadditon reactions.
Article
Chemistry, Organic
Nikolai A. Sitte, Maximilian Menche, Pavel Tuzina, Frank Bienewald, Ansgar Schaefer, Peter Comba, Frank Rominger, A. Stephen K. Hashmi, Thomas Schaub
Summary: The vinylation of various nucleophiles with acetylene is achieved using organocatalysis with easily accessible phosphines. A detailed mechanistic investigation supports a nucleophilic activation of acetylene by the phosphine catalyst. Various organic compounds were successfully synthesized through this method.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Danqing Ji, Zisong Qi, Xingwei Li
Summary: In this study, a straightforward and efficient enantioselective hydrophosphination of gem-difluoroallenes using disubstituted phosphines was developed. A wide range of enantioenriched fluorinated allylic phosphines were successfully synthesized with excellent regio- and enantioselectivity, demonstrating their potential for synthetic and catalytic applications.
Article
Chemistry, Multidisciplinary
Ze-ren Yang, Hou-ze Gui, Min Shi
Summary: A new method for substitution of allenoate using oxindoles as nucleophilic reagents has been developed in this study under phosphine catalysis, leading to 3-allenic or 3-dienoic oxindoles. Plausible reaction mechanisms have been proposed based on previous works.
Article
Chemistry, Multidisciplinary
Hongtao Xu, Yan Wang, Hewei Dong, Yiyuan Zhang, Yuang Gu, Shuning Zhang, Yu Meng, Jie Li, Xiao Jie Shi, Qun Ji, Lili Liu, Peixiang Ma, Fei Ma, Guang Yang, Wei Hou
Summary: Click chemistry is a concept of using modular synthesis for rapid functional discovery. This report describes the development of a clickable C3-H selenylation of indole and highlights its potential in high-throughput medicinal chemistry and chemical biology.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Marta Papis, Raffaella Bucci, Alessandro Contini, Maria Luisa Gelmi, Leonardo Lo Presti, Giovanni Poli, Gianluigi Broggini, Camilla Loro
Summary: A phosphine-catalyzed domino assembly of six units of 2-bromomethyl acrylates was developed to synthesize polyalkenyl adducts containing two cyclohexenyl rings. This method involves initial dimerization and subsequent trimerization of the substrate, resulting in the formation of seven carbon-carbon bonds and four stereocenters. The protocol has also been successfully scaled up to gram-scale experiments.
Article
Chemistry, Multidisciplinary
Jozafina Milicaj, Vasudeva R. Dodda, Kaelan R. Patel, Ingrid Rodriguez Aragon, Timothy O'Connell, Ramaiah Muthyala, Erika A. Taylor, Yuk Y. Sham
Summary: Research has shown that using practical examples in undergraduate education can improve retention rates of historically underrepresented students in STEM majors and reduce achievement gaps. This study presents a laboratory experiment that translates medicinal chemistry synthesis into a method suitable for undergraduate labs, resulting in the successful synthesis of a clinically important drug and its analogues. The experiment introduces various concepts and analytical techniques, enhancing student learning in the field.
JOURNAL OF CHEMICAL EDUCATION
(2022)
Article
Chemistry, Multidisciplinary
Chaofan Huang, Fuchun Shi, Yifan Cui, Can Li, Jie Lin, Qi Liu, Anni Qin, Huanan Wang, Guolin Wu, Penglin Wu, Junzhe Xiao, Haibo Xu, Yuan Yuan, Yizhan Zhai, Wei-Feng Zheng, Yangguangyan Zheng, Biao Yu, Shengming Ma
Summary: A palladium-catalyzed C-O bond formation reaction between phenols and allenylic carbonates has been developed, yielding 2,3-allenic aromatic ethers with good to excellent yields under mild conditions. This method tolerates various functional groups and has been demonstrated to be synthetically useful through transformations of the allene moiety. Total syntheses of naturally occurring allenic aromatic ethers, eucalyptene and terricollene A, have been achieved by utilizing this reaction as a key step.
Review
Biochemistry & Molecular Biology
Dmitry Korolev, Viktor Postnov, Ilia Aleksandrov, Igor Murin
Summary: This review presents the main patterns of synthesis for theranostics platforms and examines various chemical methods and modern solutions applied in the field of medicine, as well as analyzing modern trends and development areas.
Article
Chemistry, Multidisciplinary
Fangxiang Sun, Shuaimin Tan, Hou-Ji Cao, Jingkai Xu, Vladimir I. Bregadze, Deshuang Tu, Changsheng Lu, Hong Yan
Summary: This research proposes a new molecular design strategy for achieving AIE properties by combining three-dimensional aromatic boron clusters of carboranes with vinyl group(s). A efficient synthesis method for boron cluster-based AIEgens is developed.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Chang Zhang, Zhiyang Lin, Yufei Zhu, Chuan Wang
Summary: A novel chromium-catalyzed reaction was reported for the efficient synthesis of gem-difluorohomoallylic alcohols, with high chemoselectivity towards formyl moiety conversion in the presence of other functionalities. Simple derivatizations of the hydroxyl group of the coupling products demonstrate the utility of this method.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Shan Shan Ng, Zicong Chen, On Ying Yuen, Chau Ming So
Summary: A novel family of phosphine ligands was designed and synthesized, which showed excellent catalytic efficiency in the synthesis of triortho-substituted biaryls. The coordination mode of the ligand with palladium was confirmed by single-crystal X-ray crystallography.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Riley D. Kirk, Marina A. Carro, Christine Wu, Mohamad Jamal Aldine, Alex M. Wharton, Danielle G. Goldstein, Margaret E. Rosario, Gina M. Gallucci, Yiwen Zhao, Elizabeth Leibovitz, Matthew J. Bertin
Summary: Students enhanced their understanding of methodologies and workflows associated with extract analysis and biological evaluation of botanical extracts through hands-on laboratory activities, and the synergy of the laboratory course with independent research contributed to workforce preparation and library generation.
JOURNAL OF CHEMICAL EDUCATION
(2021)
Article
Polymer Science
Shengqi Liu, Ye Meng, Hu Li, Song Yang
Summary: By modifying Cr-based metal-organic frameworks (MOFs) MIL-101, this study improved the acidic sites of the catalyst and proposed a new efficient route for the condensation of furfural with alkyl alcohols. Through the investigation of different catalysts, reaction conditions, and catalyst properties, a new method for high-yield production of acetals at room temperature without solvent was discovered.
Article
Chemistry, Organic
Jovana Aleksic, Milovan Stojanovic, Jaksa Boskovic, Marija Baranac-Stojanovic
Summary: We developed a green and atom-economical method using solid-state silica gel catalysis for the synthesis of polysubstituted 1,4- and 1,2-dihydropyridines (DHPs) from commercially available materials, amines, and ethyl propiolate. By heating the reactants and silica gel in a closed vessel, the DHP skeleton was assembled. Aliphatic amines predominantly produced 1,4-isomers of DHPs, while reactions with aromatic amines yielded a mixture of 1,4- and 1,2-isomers. Addition of 1% mass percent of H2SO4 to silica gel shifted the product distribution towards 1,4-DHPs.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Dermatology
Hongsheng Wang, Haiqin Jiang, Rosane M. B. Teles, Yanqing Chen, Aiping Wu, Jing Lu, Zhimin Chen, Feiyang Ma, Matteo Pellegrini, Robert L. Modlin
JOURNAL OF INVESTIGATIVE DERMATOLOGY
(2020)
Article
Multidisciplinary Sciences
Kindra M. Kelly-Scumpia, Aaron Choi, Roksana Shirazi, Hannah Bersabe, Esther Park, Philip O. Scumpia, Maria T. Ochoa, Jing Yu, Feiyang Ma, Matteo Pellegrini, Robert L. Modlin
Article
Immunology
Travis K. Hughes, Marc H. Wadsworth, Todd M. Gierahn, Tran Do, David Weiss, Priscila R. Andrade, Feiyang Ma, Bruno J. De Andrade Silva, Shuai Shao, Lam C. Tsoi, Jose Ordovas-Montanes, Johann E. Gudjonsson, Robert L. Modlin, J. Christopher Love, Alex K. Shalek
Article
Medicine, Research & Experimental
George W. Agak, Alice Mouton, Rosane M. B. Teles, Thomas Weston, Marco Morselli, Priscila R. Andrade, Matteo Pellegrini, Robert L. Modlin
Summary: A specific subset of T(H)17 cells, termed antimicrobial T(H)17 cells, were generated with varying antimicrobial activity and shown to release T cell extracellular traps (TETs) containing histone H2B-decorated DNA to capture and kill bacteria, including Cutibacterium acnes. These cells were found to rely on the secretion of granulysin, granzyme B, perforin, and histone H2B for their antimicrobial activity.
JOURNAL OF CLINICAL INVESTIGATION
(2021)
Article
Immunology
Rui Yang, Ying Peng, Jiang Pi, Yidian Liu, Enzhuo Yang, Xiaona Shen, Lan Yao, Ling Shen, Robert L. Modlin, Hongbo Shen, Wei Sha, Zheng W. Chen
Summary: The primary CD4+CD161+ T-cell subset in unexposed individuals can quickly inhibit the growth of intracellular Mtb and BCG, but these cells lose this ability in TB patients.
FRONTIERS IN IMMUNOLOGY
(2021)
Article
Dermatology
Shuai Shao, Lam C. Tsoi, William R. Swindell, Jiaoling Chen, Ranjitha Uppala, Allison C. Billi, Xianying Xing, Chang Zeng, Mrinal K. Sarkar, Rachael Wasikowski, Yanyun Jiang, Joseph Kirma, Jingru Sun, Olesya Plazyo, Gang Wang, Paul W. Harms, John J. Voorhees, Nicole L. Ward, Feiyang Ma, Matteo Pellegrini, Alexander Merleev, Bethany E. Perez White, Robert L. Modlin, Bogi Andersen, Emanual Maverakis, Stephan Weidinger, J. Michelle Kahlenberg, Johann E. Gudjonsson
Summary: The research reveals the critical role of IRAK2 in the severity of atopic dermatitis and psoriasis, with inhibition of IRAK2 normalizing differentiation and inflammation. These findings suggest that IRAK2 promotes feed-forward amplification of inflammatory responses in the skin through modulation of differentiation pathways and inflammatory responses.
JOURNAL OF INVESTIGATIVE DERMATOLOGY
(2021)
Article
Immunology
Feiyang Ma, Travis K. Hughes, Rosane M. B. Teles, Priscila R. Andrade, Bruno J. de Andrade Silva, Olesya Plazyo, Lam C. Tsoi, Tran Do, Marc H. Wadsworth, Aislyn Oulee, Maria Teresa Ochoa, Euzenir N. Sarno, M. Luisa Iruela-Arispe, Eynav Klechevsky, Bryan Bryson, Alex K. Shalek, Barry R. Bloom, Johann E. Gudjonsson, Matteo Pellegrini, Robert L. Modlin
Summary: The study identified a set of genes involved in antimicrobial responses that are differentially expressed in reversal reactions (RRs) lesions compared to lepromatous leprosy (L-lep) lesions, regulated by interferon-gamma and interleukin-1 beta. By integrating spatial coordinates of key cell types and antimicrobial gene expression, a map depicting the organized architecture of granulomas in RR and T-lep lesions was constructed, showing compositional and functional layers contributing to the antimicrobial response. Modlin and colleagues utilized single-cell RNA sequencing with cellular spatial mapping to examine the architecture of granulomas in leprosy lesions, providing insights from localized disease (tuberculoid leprosy, reversal reaction) to progressive infection (lepromatous leprosy).
Article
Immunology
Aislyn Oulee, Feiyang Ma, Rosane M. B. Teles, Bruno J. de Andrade Silva, Matteo Pellegrini, Eynav Klechevsky, Andrew N. Harman, Jake W. Rhodes, Robert L. Modlin
Summary: LCs in the epidermis contain genes that contribute to antimicrobial responses, including chemokines such as CCL1, CCL17, CCL19, CCL2, CCL22, CXCL14, and CXCL2, which mediate both antimicrobial and inflammatory responses. These genes encode proteins with broad antibacterial activity, including against Staphylococcus aureus, the leading cause of skin infections.
FRONTIERS IN IMMUNOLOGY
(2021)
Article
Dermatology
Lam C. Tsoi, Xianying Xing, Enze Xing, Rachael Wasikowski, Shuai Shao, Chang Zeng, Olesya Plazyo, Joseph Kirma, Yanyung Jiang, Allison C. Billi, Mrinal K. Sarkar, Jessica L. Turnier, Ranjitha Uppala, Kathleen M. Smith, Yolanda Helfrich, John J. Voorhees, Emanual Maverakis, Robert L. Modlin, J. Michelle Kahlenberg, Victoria E. Scott, Johann E. Gudjonsson
Summary: This study demonstrates that tape stripping with optimized high-resolution transcriptomic profiling can effectively assess and characterize inflammatory responses in the skin. By comparing different samples and sampling methods, the study shows that tape stripping can capture the transcriptome of the upper layers of the skin, providing insights into the molecular components of the immune amplification pathway in psoriasis. Additionally, the study suggests that nonlesional psoriatic skin exhibits activated, proinflammatory changes, which are not captured by full-thickness skin biopsy transcriptome profiling.
JOURNAL OF INVESTIGATIVE DERMATOLOGY
(2022)
Article
Cell Biology
Allison C. Billi, Feiyang Ma, Olesya Plazyo, Mehrnaz Gharaee-Kermani, Rachael Wasikowski, Grace A. Hile, Xianying Xing, Christine M. Yee, Syed M. Rizvi, Mitra P. Maz, Celine C. Berthier, Fei Wen, Lam C. Tsoi, Matteo Pellegrini, Robert L. Modlin, Johann E. Gudjonsson, J. Michelle Kahlenberg
Summary: This study analyzed the skin and circulating immune cells of lupus patients using integrated single-cell RNA sequencing and spatial RNA sequencing. The findings reveal that the normal-appearing skin of patients with lupus is characterized by an interferon-rich environment and that CD16+ dendritic cells undergo interferon education in the skin, leading to proinflammatory phenotypes. These results provide important insights into the pathogenesis of cutaneous lupus erythematosus.
SCIENCE TRANSLATIONAL MEDICINE
(2022)
Article
Immunology
Tran H. Do, Feiyang Ma, Priscila R. Andrade, Rosane Teles, Bruno J. de Andrade Silva, Chanyue Hu, Alejandro Espinoza, Jer-En Hsu, Chun-Seok Cho, Myungjin Kim, Jingyue Xi, Xianying Xing, Olesya Plazyo, Lam C. Tsoi, Carol Cheng, Jenny Kim, Bryan D. Bryson, Alan M. O'Neill, Marco Colonna, Johann E. Gudjonsson, Eynav Klechevsky, Jun Hee Lee, Richard L. Gallo, Barry R. Bloom, Matteo Pellegrini, Robert L. Modlin
Summary: Acne, a common skin condition affecting 1 in 10 people globally, is characterized by disfiguring facial lesions. This study explored the mechanisms underlying the disease using single-cell and spatial RNA sequencing, as well as ultrahigh-resolution Seq-Scope analysis. The researchers identified TREM2 macrophages expressing lipid metabolism and proinflammatory genes near the hair follicle epithelium, which expressed squalene epoxidase. Through in vitro experiments, it was discovered that squalene induced differentiation of TREM2 macrophages, impairing their ability to kill Cutibacterium acnes. Additionally, the addition of squalene to macrophages inhibited oxidative enzymes and scavenged oxygen free radicals, providing insights into the efficacy of benzoyl peroxide in acne treatment. These findings contribute to our understanding of the role of TREM2 macrophages and unsaturated lipids in the pathogenesis of acne, as well as their similarity to atherosclerosis.
SCIENCE IMMUNOLOGY
(2022)
Article
Biology
Erin W. Meermeier, Christina L. Zheng, Jessica G. Tran, Shogo Soma, Aneta H. Worley, David Weiss, Robert L. Modlin, Gwendolyn Swarbrick, Elham Karamooz, Sharon Khuzwayo, Emily B. Wong, Marielle C. Gold, David M. Lewinsohn
Summary: Human lung-resident MAIT cells are polycytotoxic, secrete antimicrobial molecules, express genes associated with persistence, and selectively express cytokine and chemokine-related molecules. These characteristics make MAIT cells early sensors in the defense of the respiratory barrier.
COMMUNICATIONS BIOLOGY
(2022)
Article
Cell Biology
Alan M. O'Neill, Marc C. Liggins, Jason S. Seidman, Tran H. Do, Fengwu Li, Kellen J. Cavagnero, Tatsuya Dokoshi, Joyce Y. Cheng, Faiza Shafiq, Tissa R. Hata, Johann E. Gudjonsson, Robert L. Modlin, Richard L. Gallo
Summary: Research has shown that adipogenic fibroblasts play a critical role in acne pathogenesis and can protect against Cutibacterium acnes infection by producing cathelicidin. The ability of C. acnes to trigger cathelicidin production in preadipocytes is dependent on TLR2. Retinoic acid (RA) treatment can suppress adipogenesis and enhance cathelicidin expression in preadipocytes, providing a potential therapeutic target for difficult-to-treat acne.
SCIENCE TRANSLATIONAL MEDICINE
(2022)
Meeting Abstract
Rheumatology
Allison Billi, Feiyang Ma, Olesya Plazyo, Grace Hile, Xianying Xing, Mehrnaz Gharaee-Kermani, Rachael Wasikowski, Lam Tsoi, Matteo Pellegrini, Robert L. Modlin, Johann Gudjonsson, J. Michelle Kahlenberg
ARTHRITIS & RHEUMATOLOGY
(2021)
Review
Immunology
Chaeuk Chung, Prashanta Silwal, Insoo Kim, Robert L. Modlin, Eun-Kyeong Jo