Correction
Chemistry, Multidisciplinary
Gao-Lan Zhang, Madhusudhan Reddy Gadi, Xikai Cui, Ding Liu, Jiabin Zhang, Varma Saikam, Christopher Gibbons, Peng G. Wang, Lei Li
Summary: The study presents a protection-group-free method for S-glycosylation, which can be applied in the synthesis of thioglycosides and thioglycopeptides in water.
Article
Chemistry, Physical
Yuting Liu, Huifang Liu, Ning Li, Feng Wang
Summary: This study reports a novel photocatalytic strategy for the oxidative C-C cleavage of lignin and β-O-4 derivatives using photoredox organocatalysts. High yields of aromatic aldehydes and phenyl formate were obtained, and mixed binary organic solvents were shown to promote bond cleavage and inhibit over-oxidation side reactions. The absorbance, excitation, and interaction with the lignin model of the photocatalyst in different solvents were investigated, and a C-centered radical intermediate was captured, providing evidence for the direct Cα-Cβ bond cleavage mechanism.
APPLIED CATALYSIS B-ENVIRONMENTAL
(2023)
Article
Chemistry, Organic
Bhavesh Deore, Ryan W. Kwok, Malika Toregeldiyeva, Jesus T. Vazquez, Mateusz Marianski, Carlos A. Sanhueza
Summary: The conformational properties of the hydroxymethyl group and glycosidic bond of aryl S-glucosides are influenced by the electronic properties of the aglycone. The rotational equilibrium of the hydroxymethyl group depends on the electron-withdrawing character of the aglycone, while the conformational equilibrium of the glycosidic bond depends on the electronic properties of the aglycone.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Peng Wen, Peijing Jia, Qiuhua Fan, Bethany J. McCarty, Weiping Tang
Summary: A streamlined iterative assembly of thio-oligosaccharides was developed by aqueous glycosylation, efficiently synthesizing 1,2-trans S-glycosides with high chemo- and stereoselectivity at room temperature. The method was successfully applied to the synthesis of a trimannoside moiety of N-linked glycans core region.
Article
Chemistry, Multidisciplinary
Xiaotong Xu, Shuqi Dai, Shuai Xu, Qi Zhu, Yuliang Li
Summary: In this study, a polymeric carbon nitride/polyhedral oligomeric silsesquioxane PDI heterojunction photocatalyst was prepared to overcome the charge localization effect and strong intermolecular aggregation in PDI, leading to improved cleavage conversion efficiency and promising application prospects.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Jincai Wang, Yingle Feng, Taotao Sun, Qi Zhang, Yonghai Chai
Summary: This study explores a photolabile protecting group (NPPOC) and its application in the consecutive synthesis of oligosaccharides. NPPOC enables efficient construction of glycosides and can be removed through photolysis. The compatibility between NPPOC's photolysis and glycosylation allows for the consecutive assembly of oligosaccharides without intermediate purification.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Rapelly Venkatesh, Varsha Tiwari, Jeyakumar Kandasamy
Summary: Preparation of S-aryl thioglycosides from 1-thiosugars via S-arylation was demonstrated under mild reaction conditions. A variety of protected and unprotected 1-thiosugars derived from different sugars underwent efficient cross-coupling reactions with functionalized aryldiazonium salts, yielding desired products with high yields within a short reaction time. Furthermore, the method was successfully applied in the synthesis of biologically relevant drugs and inhibitors.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Chen Zhang, Hao Zuo, Ga Young Lee, Yike Zou, Qiu-Di Dang, K. N. Houk, Dawen Niu
Summary: The chemistry of carbohydrates has a long history, and a simple, stereoselective and efficient glycosylation method is still needed for studying sugars. This study presents a strategy for 1,2-cis-glycosylation without using metals or strong acids. The method activates glycosyl donors through a radical cascade, resulting in the formation of 1,2-cis-glycosides with high stereoselectivity. The reaction shows remarkable tolerance to functional groups and is applicable to a broad range of donors.
Article
Chemistry, Organic
Bhavesh Deore, Joseph E. Ocando, Lan D. Pham, Carlos A. Sanhueza
Summary: A voltammetric study of alkyl and arylS-glucosides revealed their reactivity patterns. The oxidation potential of alkylS-glucosides is influenced by the steric properties of the aglycone, with bulky groups leading to higher oxidation potentials. In contrast, arylS-glucosides' oxidation potentials correlate with the substituents' parameters and radical stabilization energies, indicating the importance of inherent stability in controlling their electrochemical reactivity. The reactivity differences between alkyl and arylS-glucosides also extend to the protective group's effect on the oxidation potential.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Akira Shiozuka, Kohei Sekine, Takumi Toki, Kyohei Kawashima, Toshifumi Mori, Yoichiro Kuninobu
Summary: This study developed a divergent deaminative borylation and hydrodeamination of primary aromatic amines using bis(pinacolato)diboron. These transformations can be switched by the reaction conditions. Mechanistic and computational studies suggested that the cleavage of the C-N bond and the formation of C-B bond do not involve free aryl radical intermediates, but hydrodeamination proceeds via hydrogen atom transfer between the corresponding aryl radical and an ethereal solvent.
Article
Chemistry, Organic
Yu-Shi Jiang, Shan-Shan Li, Xue-Ling Luo, Li-Ning Chen, Dan-Na Chen, Peng-Ju Xia
Summary: A metal-free difunctionalization strategy for diazenes was developed using bifunctionalization reagents, leading to the construction of over 30 triazane core motifs. This strategy involves a unique N(sp(3))-N(sp(2)) radical coupling between the hydrazine radical and the imine radical, allowing the efficient installation of imines and various functional groups on both ends of the nitrogen-nitrogen bond of diazenes.
Article
Chemistry, Multidisciplinary
Farnaz Jafarpour, Banafshe Rahimi
Summary: A novel controlled DTBP-mediated oxidative C-S bond cleavage/annulation cascade is developed, allowing benzyl thioethers to form carbonyl intermediates and participate in annulation reactions with alkynes to produce privileged indenone skeletons.
NEW JOURNAL OF CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Ke Yang, Qin Li, Zhengyi Li, Xiaoqiang Sun
Summary: The activation and transformation of organic chemical bonds, specifically C-S bond cleavage, has been a major focus in organic chemistry. While transition metal strategies have made significant progress, novel transition-metal-free strategies using halogenated reagents, oxidants, acids, bases, and organic photochemical and electrochemical methods have also been developed. However, a comprehensive review of transition-metal-free strategies has not been reported. This review provides a comprehensive overview of the major advances in transition-metal-free C-S bond cleavage and transformation of organosulfur compounds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Qu-Ping Hu, Yu-Tao Liu, Yong-Ze Liu, Fei Pan
Summary: A method for the remote regioselective alkynylation of unactivated C(sp(3))-H bonds in diverse aliphatic amides by photogenerated amidyl radicals has been developed. The site-selectivity is dominated via a 1,5-hydrogen atom transfer (HAT) process of the amide. Mild reaction conditions and high regioselectivity are demonstrated in this methodology.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Yasuharu Kanda, Ryo Saito, Taiki Ono, Kenichi Kon, Takashi Toyao, Shinya Furukawa, Yasushi Obora, Ken-ichi Shimizu
Summary: The addition of a second metal (Ru, Pt, and Ir) to SiO2-supported Rh phosphide catalysts enhances the hydrodesulfurization (HDS) activity. Among the Rh-M-P catalysts, Rh-Pt-P catalyst exhibits the highest HDS activity, where Pt and Rh cooperate as active sites to enhance the C-S bond cleavage.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Miao Liu, Kai-Meng Liu, De-Cai Xiong, Hanyu Zhang, Tian Li, Bohan Li, Xianjin Qin, Jinhe Bai, Xin-Shan Ye
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2020)
Article
Chemistry, Organic
Qiannan Zheng, Shengbiao Tang, De-Cai Xiong, Qin Li, Xin-Shan Ye
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Srikrishna Bera, Runze Mao, Xile Hu
Summary: The enantioselective cross-coupling of non-activated alkyl halides with alkenyl boronates enables the synthesis of chiral alkyl boronates, which is a useful method for drug development. This reaction proceeds via nickel hydride insertion into an internal alkene followed by nickel-catalysed alkyl-alkyl cross-coupling.
Article
Chemistry, Multidisciplinary
Xiangli Yi, Runze Mao, Lara Lavrencic, Xile Hu
Summary: The study presents a decarboxylative coupling reaction using photoredox and copper catalysis to convert alkyl carboxylic acids into polyfluoroaryl compounds. The method demonstrates broad scope and good functional group compatibility, with the potential to achieve a wide range of F-substitution patterns on the aryl groups. Mechanistic study suggests a [Cu-(Ar-F)(2)] species may be responsible for the transfer of polyfluoroaryl groups to alkyl radicals.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Miao Liu, Zhao-Xiang Luo, Tian Li, De-Cai Xiong, Xin-Shan Ye
Summary: A new electrochemical approach for trifluoromethylation of glycals using CF3SO2Na and MnBr2 has been reported, resulting in trifluoromethylated glycals with different protective groups in high yields. The successful capture of a CF3 radical suggests a radical mechanism is involved in this reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Kai-Meng Liu, Peng-Yu Wang, Zhen-Yan Guo, De-Cai Xiong, Xian-Jin Qin, Miao Liu, Meng Liu, Wan-Ying Xue, Xin-Shan Ye
Summary: We report a visible-light-promoted 2-deoxyglycosylation reaction of alcohols with glycals, which exhibits high efficiency, excellent stereoselectivity, and the capability to synthesize glycosylated compounds with different chain lengths.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Biochemistry & Molecular Biology
Xia Wu, Biao Wu, Chen-Fei Gao, Xin-Shan Ye, De-Cai Xiong
Summary: Two photoreactions have been developed for the synthesis of 1- and 2-deoxysugars using thioglycosides. The use of Hantzsch ester as an additive allows for the synthesis of a wide range of 1-deoxysugars under UV light without an exogenous photosensitizer, while the utilization of TTBP as the additive results in the production of various 2-deoxysugars from their corresponding thioglycosides. The methodology has a broad substrate scope, high functional group tolerance, and scalability to gram-scale reactions.
JOURNAL OF CARBOHYDRATE CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Zhao-Xiang Luo, Miao Liu, Tian Li, De-Cai Xiong, Xin-Shan Ye
Summary: In this study, a convenient one-step electrochemical bromination of glycals was achieved using Bu4NBr as the brominating source under metal-catalyst-free and oxidant-free conditions. A series of 2-bromoglycals were successfully synthesized and further used in coupling reactions to efficiently produce 2C-branched carbohydrates and disaccharides. Radical trapping and cyclic voltammetry experiments suggested the involvement of bromine radicals in the reaction process.
FRONTIERS IN CHEMISTRY
(2021)
Article
Biochemical Research Methods
Chang-Cheng Liu, Chang-Xin Huo, Canjia Zhai, Xiu-Jing Zheng, De-Cai Xiong, Xin-Shan Ye
Summary: The study focuses on the glycosylation and conformational limitations of the HIV-1 envelope protein. A synthetic approach for Man5 and its analogues was developed, and their immunogenicity was evaluated in mice. The modified analogues induced stronger immune responses but failed to bind the native antigen.
BIOCONJUGATE CHEMISTRY
(2022)
Article
Chemistry, Physical
Juner Zhang, Ailiena O. Maggiolo, Edwin Alfonzo, Runze Mao, Nicholas J. Porter, Nayla M. Abney, Frances H. Arnold
Summary: This study demonstrates that engineered enzymes can achieve new-to-nature C-H alkylation with distinct selectivities. The research also reveals that minimal changes to the enzyme's structure can tune its chemoselectivity.
Article
Biochemistry & Molecular Biology
Yang Liu, Bohan Li, Xiujing Zheng, Decai Xiong, Xinshan Ye
Summary: KH-1 is a valuable target for antitumor vaccines, but most TACAs tend to induce immunological tolerance. To overcome this, fluorinated derivatives of KH-1 were designed and conjugated to CRM197 to form glycoconjugates. These modified KH-1 conjugates were found to induce higher titers of antibodies, particularly IgG, which can recognize and eliminate KH-1-positive cancer cells through CDC. The trifluoro-modified KH-1-TF-CRM197 shows great potential as an anticancer vaccine candidate.
Article
Chemistry, Multidisciplinary
Runze Mao, Daniel J. J. Wackelin, Cooper S. S. Jamieson, Torben Rogge, Shilong Gao, Anuvab Das, Doris Mia Taylor, K. N. Houk, Frances H. H. Arnold
Summary: By engineering bacterial cytochrome P450, chiral 1,2,3-polysubstituted cyclopropanes can be synthesized regardless of the stereopurity of the olefin substrates used. This new method simplifies the synthesis of chiral cyclopropanes and expands the application of classical cyclopropanation methods.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Review
Biochemistry & Molecular Biology
Xingxing Wei, Pengyu Wang, Fen Liu, Xinshan Ye, Decai Xiong
Summary: This review presents the development of glycomimetics, the methods of fluorination of carbohydrates, and the effects of fluorination on the properties and biological activities of sugars.
Article
Chemistry, Multidisciplinary
Yafei Cao, Minmin Zhou, Run-Ze Mao, You Zou, Feng Xia, Da-Ke Liu, Jianhui Liu, Qin Li, De-Cai Xiong, Xin-Shan Ye
Summary: A new glycosylation method using visible light and 3,5-dimethoxyphenyl glycoside as the donor was developed, which delivers O-glycosides and N-glycosides in moderate to excellent yields with a wide range of O-nucleophiles and nucleobases as the glycosyl acceptors.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Hanyu Zhang, Meng Liu, Xia Wu, Miao Liu, Decai Xiong, Xinshan Ye
PROGRESS IN CHEMISTRY
(2020)
