Article
Chemistry, Multidisciplinary
Muhammad Asif Iqbal, Le Lu, Hina Mehmood, Ruimao Hua
Summary: This study reports a Cs2CO3-promoted cross-coupling reaction of arenes with cyano-/nitro-substituted aryl halides in DMSO to afford biaryls in the absence of ligands. The cyano/nitro groups in biaryls are shown to be useful for further transformations. Additionally, the formation of dibenzofurans from reactions between arenes and 1-bromo-2-iodobenzene is reported. A radical mechanism for the formation of biaryls is proposed based on control experiments and theoretical studies.
Article
Chemistry, Multidisciplinary
Makoto Hashimoto, Susumu Watari, Takaaki Taguchi, Kazuki Ishikawa, Takuya Kumamoto, Susumu Okamoto, Koji Ichinose
Summary: In this study, we identified two enzymes, ActVA-ORF4 and ActVA-ORF3, involved in the last step of ACT biosynthesis. ActVA-ORF4 catalyzes the intermolecular C-C bond formation using DHK-OH as the substrate, while ActVA-ORF3 is a quinone-forming enzyme that produces the coupling substrate DHK-OH and the final product ACT.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Carmela Molinaro, Yukie Kawasaki, George Wanyoike, Taiki Nishioka, Tsuyoshi Yamamoto, Brad Snedecor, Sarah J. Robinson, Francis Gosselin
Summary: Through modification of cytochrome P450 enzymes, a scalable oxidative carbon-carbon coupling process has been developed for the production of arylomycin antibiotic cores. This new approach provides a viable, scalable, and practical route for the synthesis of novel antibiotics.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Seong-Ryeong Go, Su-Jin Lee, Woo-Chan Ahn, Kwang-Hyun Park, Eui-Jeon Woo
Summary: The diterpene glycosyltransferase UGT76G1 plays a key role in the biosynthesis of rebaudioside A, but its poor thermostability limits its industrial application. In this study, a computational design strategy was used to generate a mutant of UGT76G1 with improved thermostability and enzymatic activity. The designed variant showed increased Tm, rebaudioside A production capacity, and reduced byproduct formation. This study highlights the effectiveness of structure-based design in introducing multiple mutations and improving the enzymatic properties of UGT76G1.
COMMUNICATIONS CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yu Tian, Xi-Tao Li, Ji-Ren Liu, Jian Cheng, Ang Gao, Ning-Yuan Yang, Zhuang Li, Kai-Xin Guo, Wei Zhang, Han-Tao Wen, Zhong-Liang Li, Qiang-Shuai Gu, Xin Hong, Xin-Yuan Liu
Summary: The study demonstrates an enantioconvergent radical C(sp(3))-S cross-coupling reaction using chiral tridentate anionic ligands and Cu(I) catalysts. This method provides a broad substrate scope, high enantioselectivity, and access to useful alpha-chiral alkyl organosulfur compounds with different sulfur oxidation states, serving as a complementary approach to known asymmetric C(sp(3))-S bond formation methods.
Article
Chemistry, Organic
Ruohua Gui, Chao-Jun Li
Summary: Historically, deuteration reactions were mainly used for mechanistic studies, but their pharmacological importance is now recognized. Efforts have been made to meet the urgent need for deuteration tools since the approval of the first deuterated drug for Huntington's disease. Current deuteration strategies involving reversible H/D exchange have limitations in functional group tolerance and deuterium content. In this study, a ruthenium-catalyzed deoxygenative deuteration of ketones was developed, allowing regiospecific deuteration with high deuterium content.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Hao Chen, Juntian Fan, Yuqing Fu, Chi-Linh Do-Thanh, Xian Suo, Tao Wang, Ilja Popovs, De-en Jiang, Yating Yuan, Zhenzhen Yang, Sheng Dai
Summary: A novel method using mechanochemical Ullmann-type reactions to promote direct aromatic ring knitting has been demonstrated to afford CPNs with high surface areas and mesoporous architecture under neat and ambient conditions. The versatility of this approach has been confirmed by successful construction of various CPNs and even highly crystalline graphite product, showing good electrochemical performance in lithium-ion batteries. This strategy expands the frontiers of CPN synthesis and provides new opportunities for their scalable applications.
ADVANCED MATERIALS
(2021)
Article
Chemistry, Multidisciplinary
Chengwei Liu, Chong-Lei Ji, Tongliang Zhou, Xin Hong, Michal Szostak
Summary: Cooperative bimetallic catalysis was used in the direct decarbonylative heteroarylation of carboxylic acids, enabling synthesis of important heterobiaryl motifs with high chemoselectivity. This method, which does not require prefunctionalization or directing groups, has a broad substrate scope and shows potential for late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to understand the reaction mechanism, identifying a key step involving the intersection of two catalytic cycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Polymer Science
Xin Gao, Zeli Song, Jianfeng Hu, Hao Zhang
Summary: An efficient protocol for synthesizing sulfur-containing polymers without transition-metal catalyst has been developed. Various sulfur-containing polymers can be produced through cross coupling polymerization of Ntosylhydrazones and thiols in the presence of K2CO3. Additionally, a one-pot, two-step conversion from ketones to polymers offers an alternative and convenient route to form C-S linkages.
Article
Chemistry, Multidisciplinary
Qingning Yang, Xiyi Li, Lu Chen, Xiaoyu Han, Feng Ryan Wang, Junwang Tang
Summary: This study presents a heterogeneous photocatalyst (Cu/ZnO) for efficient C-C coupling of benzyl chloride with high selectivity and yield at room temperature. The reaction showed excellent stability even after 8 cycles. The enhanced adsorption, stabilization of intermediates, and charge separation/transfer contributed to the improved performance.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yi-Fan Zhang, Han-Nan Chen, Yi Xiao, Zhencun Cui, Wei David Wang, Guo-Qiang Xu
Summary: Here, a novel protocol for synthesizing alpha-functionalized saturated aza-heterocycles is presented, allowing for the easy installation of various nucleophilic groups. Additionally, a range of biologically valuable 3,3'-diindolylmethane derivatives can be readily synthesized under mild photocatalytic conditions.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Xue Zhang, Kun Zhao, Zhenhua Gu
Summary: Arising from restricted rotation in single bonds due to steric or electronic effects, atropisomerism is a fundamental category for molecules to exhibit their three-dimensional characters, particularly in axially chiral biaryl compounds. Despite the widespread occurrence of axially chiral skeletons in natural products and bioactive molecules, catalytic asymmetric methods for their synthesis face challenges in controlling stereoselectivity for highly sterically hindered variants. However, recent studies have shown successful direct asymmetric synthesis of biaryl atropisomers through transition metal catalysis, offering insights into the activation of substrates and changes in chemoselectivity through torsional strain-promoted ring-opening reactions.
ACCOUNTS OF CHEMICAL RESEARCH
(2022)
Article
Chemistry, Organic
Jin Zhang, Pei Zhang, Yangmin Ma, Michal Szostak
Summary: This study reports a novel solvent-free method for synthesizing ketones with high selectivity from acyl chlorides and boronic acids. The reaction takes place in the solid state, without the use of solvents, and has a short reaction time, demonstrating excellent selectivity for C(acyl)-Cl bond cleavage.
Article
Chemistry, Multidisciplinary
Yoshiya Sekiguchi, Naohiko Yoshikai
Summary: A zinc-catalyzed beta-allylation of cyclopropanols with Morita-Baylis-Hillman (MBH) carbonates was reported, maintaining the cyclopropane ring and yielding cyclopropyl-fused alpha-alkylidene-delta-valerolactone derivatives. The mechanism involves zinc homoenolate formation and enolization, followed by alpha-allylation with MBH carbonate leading to cyclopropane ring regeneration and irreversible lactonization, allowing for beta-functionalization with alkylidenemalononitrile as well. This reaction provides a pathway to transform simple cyclopropanols into alpha,beta- or beta,beta-difunctionalized ketones.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Li Xu, Xiaoyi Liu, Gregory R. Alvey, Andrey Shatskiy, Jian-Quan Liu, Markus D. Karkas, Xiang-Shan Wang
Summary: The study presents a protocol for silver-catalyzed controlled intermolecular cross-coupling of silyl enolates, enabling the efficient preparation of a range of synthetically useful 1,4-diketones with good functional group tolerance. Preliminary mechanistic investigations indicate that the reaction proceeds through a one-electron process involving free radical species, with PhBr acting as the oxidant.
Article
Multidisciplinary Sciences
Wei Tang, Zhengyan Guo, Zhenju Cao, Min Wang, Pengwei Li, Xiangxi Meng, Xuejin Zhao, Zhoujie Xie, Wenzhao Wang, Aihua Zhou, Chunbo Lou, Yihua Chen
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2018)
Article
Plant Sciences
Chunzhi Gao, Zhengyan Guo, Xingzhong Lu, Haiyan Chen, Liwei Liu, Zhiguo Yu, Yihua Chen
JOURNAL OF NATURAL PRODUCTS
(2018)
Article
Multidisciplinary Sciences
Tingting Hao, Zhoujie Xie, Min Wang, Liwei Liu, Yuwei Zhang, Weicang Wang, Zhao Zhang, Xuejin Zhao, Pengwei Li, Zhengyan Guo, Shushan Gao, Chunbo Lou, Guodong Zhang, Justin Merritt, Geoff P. Horsman, Yihua Chen
NATURE COMMUNICATIONS
(2019)
Article
Biotechnology & Applied Microbiology
Yuwei Zhang, Min Wang, Jun Tian, Jia Liu, Zhengyan Guo, Wei Tang, Yihua Chen
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
(2020)
Article
Chemistry, Organic
Min Wang, Zhoujie Xie, Shoubin Tang, Ee Ling Chang, Yue Tang, Zhengyan Guo, Yinglu Cui, Bian Wu, Tao Ye, Yihua Chen
Article
Chemistry, Organic
Wei Tang, Pengwei Li, Meng Chen, Zhengyan Guo, Yihua Chen
Article
Cell Biology
Shanshan Qiao, Li Bao, Kai Wang, Shanshan Sun, Mingfang Liao, Chang Liu, Nan Zhou, Ke Ma, Yuwei Zhang, Yihua Chen, Shuang-Jiang Liu, Hongwei Liu
Article
Plant Sciences
Yue Tang, Min Wang, Hua Qin, Xiangxiang An, Zhengyan Guo, Guoliang Zhu, Lixin Zhang, Yihua Chen
JOURNAL OF NATURAL PRODUCTS
(2020)
Article
Multidisciplinary Sciences
Pengwei Li, Meng Chen, Wei Tang, Zhengyan Guo, Yuwei Zhang, Min Wang, Geoff P. Horsman, Jin Zhong, Zhaoxin Lu, Yihua Chen
Summary: The biosynthesis of Aurantinins involves a unique on-line methyl esterification strategy that plays a crucial role in the overall process. This strategy utilizes a methyl ester bond to protect the carboxyl terminus, preventing unwanted side reactions and protecting producing organisms from toxic intermediates. The study reveals a widespread distribution of this initiation strategy for polyketide biosynthesis in various bacteria.
NATURE COMMUNICATIONS
(2021)
Article
Biotechnology & Applied Microbiology
Meng Chen, Zhenju Cao, Wei Tang, Min Wang, Yihua Chen, Zhengyan Guo
Summary: In this study, a high yield strain S. albus 1597 was obtained by placing the biosynthetic gene cluster (BGC) of septacidin under the control of a strong promoter. This strain was able to produce new septacidin congeners, including SEP-552 which exhibited moderate antifungal activity. The investigation of structure-activity relationship showed that the antifungal activity of septacidins is influenced by the length and decoration of their fatty acyl chains.
JOURNAL OF ANTIBIOTICS
(2022)
Editorial Material
Biotechnology & Applied Microbiology
Yue Ma, Zhengyan Guo, Binbin Xia, Yuwei Zhang, Xiaolin Liu, Ying Yu, Na Tang, Xiaomei Tong, Min Wang, Xin Ye, Jie Feng, Yihua Chen, Jun Wang
NATURE BIOTECHNOLOGY
(2022)
Review
Biochemistry & Molecular Biology
Zhengyan Guo, Yue Tang, Wei Tang, Yihua Chen
Summary: Glycosylated natural products containing heptoses show potential as drugs for treating human and animal diseases. These heptose-containing natural products can be categorized into four groups based on their structures, exhibiting antibacterial, antifungal, antitumor, and pain relief activities. Their biosynthesis and chemical synthesis studies have attracted significant interest in understanding construction mechanisms and structure-activity relationships.
NATURAL PRODUCT REPORTS
(2021)