Article
Chemistry, Multidisciplinary
Mandeep S. Dhak, Dhanarajan Arunprasath, Stephen P. Argent, James D. Cuthbertson
Summary: This article describes a photoredox-mediated radical amidation ring-expansion sequence that allows the generation of all-carbon quaternary centers with a protected aminomethyl substituent. The methodology can be applied to both styrene and unactivated alkene substrates, resulting in the concise synthesis of structurally diverse sp(3)-rich amine derivatives.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Martin Piesch, Stephan Reichl, Michael Seidl, Gabor Balazs, Manfred Scheer
Summary: A synthetic pathway was developed for the synthesis of novel anionic sandwich complexes with cyclo-E-3 (E=P, As) ligands, which were further utilized to obtain various types of complexes. The reaction pathway was elucidated using DFT calculations, leading to the successful isolation of heteroatomic complexes with unique structures.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Vladyslav Smyrnov, Jerome Waser
Summary: An electrophile-induced semipinacol rearrangement of cyclopropenylcarbinols is described, enabling the synthesis of polyfunctionalized cyclopropanes under mild metal-free conditions. The reaction demonstrates broad scope, accommodating various electrophiles, migrating groups, and substitution patterns on the cyclopropene. It is particularly useful for the synthesis of small ring-containing spirocycles, which are important building blocks in medicinal chemistry.
Article
Chemistry, Organic
Sebastian Fischer, Terrence-Thang H. Nguyen, Andreas Ratzenboeck, Huw M. L. Davies, Oliver Reiser
Summary: A stereoselective, solvent- and metal-free method for endocyclic C-C bond cleavage of monocyclopropanated cyclopentadienes mediated by strong acids has been developed. It leads to the formation of highly functionalized six-membered carbocycles with high stereocontrol. The critical step involves the formation of a cyclopropyl carbocation that undergoes endocyclic ring opening through an SN2'-type attack of various nucleophiles. Subsequent synthetic transformations demonstrate the versatility of the resulting cyclohexenes for the synthesis of compounds with nonconventional substitution patterns.
Article
Chemistry, Applied
Evgeniya S. Shutovskaya, Yulia P. Ustimenko, Alexey V. Tkachev, Julia V. Burykina, Alexander M. Agafontsev, Anastasiya V. Lastovka, Dmitriy N. Polovyanenko, Taisiya S. Sukhikh
Summary: In this study, the Pd-catalyzed cross-coupling reaction between α-pinene derivative - pinacarvone O-methyl oxime and aryl halides was described. Surprisingly, the formation of the C-C coupling product was accompanied by an unexpected opening of the pinene bicyclic structure. The reaction conditions were carefully optimized and the reaction mechanism was proposed based on structural and computational data analysis.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Zhikun Tong, Xiang Li, Jingyu Dong, Rui Gao, Qiang Deng, Jun Wang, Zheling Zeng, Ji-Jun Zou, Shuguang Deng
Summary: Developing a catalyst to upgrade furfural to alcohols is important for fine chemical synthesis. Metal phosphate nanoparticles with different compositions were synthesized, showing high catalytic efficiency for producing alcohols. The catalysts displayed high activity and stability during recycling experiments.
Article
Chemistry, Organic
Figueroa-Valverde Lauro, Diaz Cedillo Francisco, Rosas-Nexticapa Marcela, Lopez-Ramos Maria, Mateu-Armand Virginia, Garcimarero-Espino E. Alejandra, Ortiz-Ake Yazmin
Summary: The study aimed to synthesize two oxacan derivatives with moderate yielding using reagents that are not expensive and do not require special conditions.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Masaaki Komatsuda, Ayane Suto, Hiroki Kondo, Hiroyuki Takada, Kenta Kato, Bunnai Saito, Junichiro Yamaguchi
Summary: This study presents a ring-opening fluorination of bicyclic azaarenes, leading to the construction of tertiary carbon-fluorine bonds. The protocol can be applied to a variety of bicyclic azaarenes and tolerate a range of functional groups. Mechanistic studies and enantioselective fluorination have also been explored.
Article
Chemistry, Applied
Chih-Wei Hsu, Yen-Ting Lu, Chi-Ping Lin, Woo-Jin Yoo
Summary: A synthetic strategy involving Simmons-Smith cyclopropanation and acid-catalyzed pinacol rearrangement was developed to transform α-hydroxy silyl enol ethers into 1-substituted bicyclo[2.1.1]hexan-5-ones. These bicyclic ketones underwent further synthetic manipulations to generate various 1,5-disubstituted bicyclo[2.1.1]hexanes, which could serve as potential bioisosteres of ortho-substituted arenes.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Chemistry, Multidisciplinary
Mykhaylo Alekseychuk, Philipp Heretsch
Summary: Natural product chemistry faces constant challenges from newly discovered, complex molecules. These complexities include unprecedented frameworks, densely packed stereogenic centres, different functional groups, and high oxidation states. Rearranged triterpenoids exemplify these complexities. Total synthesis of these compounds often reaches the limits of feasibility in terms of steps and yield, leading to the exploration of semisynthetic approaches. This featured article discusses efficient and economic syntheses of complex terpenoid natural products and delves into the underlying rationale of biogenetic space-guided synthetic analysis.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Tushar Singha, Ganesh Arjun Kadam, Durga Prasad Hari
Summary: The Dowd-Beckwith reaction is a powerful method for synthesizing medium to large-sized carbocyclic scaffolds by ring-expansion of carbonyl compounds via alkoxy radicals. However, its synthetic applications are hampered by the dominating pathway of Dowd-Beckwith ring-expansion followed by H-atom abstraction, and there is currently no report on the functionalization of ring-expanded radicals using non-carbon based nucleophilic reagents.
Article
Chemistry, Applied
Wen-Jing Yan, Hai-Yong Tu, Zhiyong Liao, Xiao-Qin Shen, Xing-Guo Zhang
Summary: A method for constructing the indane skeleton was described, involving a palladium-catalyzed ring-opening diarylation of Cyclobutanols with aryl 1,2-dihalides. The reaction proceeds through beta-carbon elimination and subsequent alpha-carbon arylation of ketone, resulting in the formation of 2-acylindanes in yields of 42-93%.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Ryota Ogura, Kazuto Satoh, Wataru Kiuchi, Kosuke Kato, Kazutada Ikeuchi, Takahiro Suzuki, Keiji Tanino
Summary: A two-step synthesis of geminal divinyl compounds from ketones was developed. An allyl titanium reagent reacted with a ketone to form a tertiary alcohol, which was then subjected to a rearrangement reaction mediated by a Bronsted acid to generate a geminal divinyl compound. Introduction of another alkene moiety followed by ring closing metathesis resulted in a bicyclic compound possessing a vinyl group at the bridgehead position.
Article
Chemistry, Multidisciplinary
Di Zhu, Yongmei Zhao, Qinglei Chong, Fanke Meng
Summary: Utilizing a chiral phosphine-Co complex, this study demonstrates the catalytic enantioselective ring-opening of oxa- and aza-bicyclic alkenes with readily available alkenylboronic acids, resulting in a wide range of multisubstituted functionalized cyclohexenes with high yield and enantioselectivity.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Hui-Hui Wu, Xiao-Zu Fan, Zhe Tang, Heng Zhang, Lu-Yu Cai, Xiao-Fan Bi, Hong-Wu Zhao
Summary: Under specific reaction conditions, the (5 + 6) cycloaddition of vinylethylene carbonates with isatoic anhydrides proceeded smoothly, yielding medium-sized N,O-containing heterocycles in reasonable chemical yields, as confirmed by X-ray diffraction analysis.
Article
Multidisciplinary Sciences
Shasha Chong, Claire Dugast-Darzacq, Zhe Liu, Peng Dong, Gina M. Dailey, Claudia Cattoglio, Alec Heckert, Sambashiva Banala, Luke Lavis, Xavier Darzacq, Robert Tjian
Article
Physics, Applied
Sijia Lu, Wei Min, Shasha Chong, Gary R. Holtom, X. Sunney Xie
APPLIED PHYSICS LETTERS
(2010)
Article
Biochemistry & Molecular Biology
Shasha Chong, Chongyi Chen, Hao Ge, X. Sunney Xie
Article
Chemistry, Organic
Yao Fu, Hua-Jing Wang, Sha-Sha Chong, Qing-Xiang Guo, Lei Liu
JOURNAL OF ORGANIC CHEMISTRY
(2009)
Article
Chemistry, Physical
Shasha Chong, Wei Min, X. Sunney Xie
JOURNAL OF PHYSICAL CHEMISTRY LETTERS
(2010)
Article
Multidisciplinary Sciences
Wei Min, Sijia Lu, Shasha Chong, Rahul Roy, Gary R. Holtom, X. Sunney Xie
Article
Multidisciplinary Sciences
Sangjin Kim, Erik Brostroemer, Dong Xing, Jianshi Jin, Shasha Chong, Hao Ge, Siyuan Wang, Chan Gu, Lijiang Yang, Yi Qin Gao, Xiao-dong Su, Yujie Sun, X. Sunney Xie
Article
Multidisciplinary Sciences
Liling Wan, Shasha Chong, Fan Xuan, Angela Liang, Xiaodong Cui, Leah Gates, Thomas S. Carroll, Yuanyuan Li, Lijuan Feng, Guochao Chen, Shu-Ping Wang, Michael V. Ortiz, Sara K. Daley, Xiaolu Wang, Hongwen Xuan, Alex Kentsis, Tom W. Muir, Robert G. Roeder, Haitao Li, Wei Li, Robert Tjian, Hong Wen, C. David Allis
Review
Biochemistry & Molecular Biology
Meagan N. Esbin, Oscar N. Whitney, Shasha Chong, Anna Maurer, Xavier Darzacq, Robert Tjian
Article
Oncology
Bo Kyung A. Seong, Neekesh Dharia, Shan Lin, Katherine A. Donovan, Shasha Chong, Amanda Robichaud, Amy Conway, Amanda Hamze, Linda Ross, Gabriela Alexe, Biniam Adane, Behnam Nabet, Fleur M. Ferguson, Bjorn Stolte, Emily Jue Wang, Jialin Sun, Xavier Darzacq, Federica Piccioni, Nathanael S. Gray, Eric S. Fischer, Kimberly Stegmaier
Summary: Fusion-transcription factors (fusion-TFs) are difficult to therapeutically target, but recent research has discovered TRIM8 as a selective E3 ubiquitin ligase for degrading a driver fusion-TF in Ewing sarcoma. Knocking out TRIM8 leads to increased levels of the fusion TF, EWS/FLI, providing a potential strategy for exploiting oncogene overdose in Ewing sarcoma and other fusion-TF driven cancers.
Review
Biochemistry & Molecular Biology
Shasha Chong, Mustafa Mir
Summary: The proteome contains a significant portion of intrinsically disordered regions (IDRs) that perform various biological functions and are linked to different diseases despite lacking well-defined 3D structures. Recent discoveries of functionally relevant biomolecular assemblies, some forming through liquid-liquid phase separation, have brought attention to IDRs. Weak, multivalent, but selective interactions between IDRs primarily drive the formation of these biomolecular assemblies according to emerging experimental and computational studies.
JOURNAL OF MOLECULAR BIOLOGY
(2021)
Article
Biochemistry & Molecular Biology
Shasha Chong, Thomas G. W. Graham, Claire Dugast-Darzacq, Gina M. Dailey, Xavier Darzacq, Robert Tjian
Summary: This study reveals that the quantity and localization of LCD-LCD interactions can influence the transcriptional regulation of genes. Excessive LCD-LCD interactions repress transcription, while confining the transcription factor to a liquid-liquid phase separation compartment also inhibits transcription.
Article
Biology
Shawn Irgen-Gioro, Shawn Yoshida, Victoria Walling, Shasha Chong
Summary: Fixing cells with paraformaldehyde (PFA) can both enhance and diminish the appearance of liquid-liquid phase separation (LLPS) in living cells. PFA fixation can cause artificial droplet-like puncta to appear in cells that do not have detectable puncta in the live condition. The protein localization in fixed cells depends on the dynamics of protein-protein interactions, the overall rate of fixation, and the difference in fixation rates of different proteins.
Review
Chemistry, Physical
Shawn R. Yoshida, Barun K. Maity, Shasha Chong
Summary: Fluorescence microscopy techniques are widely used in biology for visualizing cellular and subcellular processes. Methods for fixing cells before imaging can induce redistribution of proteins and result in artifacts. This review discusses the ability of commonly used fixation methods to preserve protein localizations and the underlying mechanisms of fixation artifacts. Alternative fixation methods are also discussed to minimize artifacts. Careful selection of a fixation method is necessary to avoid artifacts in fixed-cell fluorescence microscopy.
JOURNAL OF PHYSICAL CHEMISTRY B
(2023)
Article
Biochemistry & Molecular Biology
Lizhen Chen, Zhao Zhang, Qinyu Han, Barun K. Maity, Leticia Rodrigues, Emily Zboril, Rashmi Adhikari, Su-Hyuk Ko, Xin Li, Shawn R. Yoshida, Pengya Xue, Emilie Smith, Kexin Xu, Qianben Wang, Tim Hui-Ming Huang, Shasha Chong, Zhijie Liu
Summary: This study reveals that androgen receptor (AR) forms condensates through multivalent interactions mediated by its N-terminal intrinsically disordered region (IDR) to orchestrate enhancer assembly in response to androgen signaling. Expansion of the poly(Q) track within AR IDR results in a higher AR condensation propensity, which affects its interactions with other enhancer components and its transcriptional activity.