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Chinese Chemical Letters 2024年第6期35卷 353-357页

作者： Jinyan Zhang Fen Liu Qian Jin Xueyi Li Qiong Zhan Mu Chen Sisi Wang Zhenlong Wu Wencai Ye Lei Wang State Key Laboratory of bioactive molecules and Druggability Assessment Jinan UniversityGuangzhou 510632China center for bioactive natural molecules and innovative drugs and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs ResearchJinan UniversityGuangzhou 510632China College of Pharmacy Jinan UniversityGuangzhou 510632China

The first phloroglucinol-triterpenoid hybrids,myrtphlotritins A-E(1-5),were rapidly recognized and isolated from two species of Myrtaceae by employing the building blocks-based molecular network(BBMN)*** 1-5 featured new carbon skeletons in which phloroglucinol derivatives were coupled with lupane-and dammarane-type triterpenoids through different linkage *** structures and absolute configurations were elucidated by comprehensive analysis of spectroscopic data and quantum chemical *** pathways for compounds 1-5 were proposed on the basis of the coexisting *** by the biogenetic pathways,the biomimetic synthesis of compound 1 was also ***,compounds 2,3,and 5 exhibited potent antiviral activities against herpes simplex virus type-1(HSV-1)infection,and compounds 2 and 5 displayed significant anti-inflammatory activities on RAW264.7 cells.

关键词： Phloroglucinol-triterpenoid adduct Myrtaceae Building blocks-based molecular network Biomimetic synthesis Antiviral activity Anti-inflammatory activity

Synthesis of Polyethylenes with In-Chain Isolated Carbonyls from CO_(2)and Ethylene via a Tandem Photoreduction/Polymerization Protocol

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CCS Chemistry 2024年第6期6卷 1591-1599页

作者： Fulin Zhou Haojie Dai Shan Tang Yongfeng Zhou Frontiers Science center for Transformative molecules Shanghai Key Laboratory for Molecular Engineering of Chiral DrugsSchool of Chemistry and Chemical EngineeringShanghai Jiao Tong UniversityShanghai 200240

Aiming at accessing polyethylene-bearing in-chain degradable functionality,copolymerization of carbon dioxide(CO_(2))with ethylene has long been recognized as a significant but highly challenging ***,most trials have resulted in ethylene homopolymerization because of the endothermic property and high energy barriers of CO_(2)insertion during polymer chain *** we report an unprecedented tandem reaction protocol for the synthesis of polyethylenes with in-chain carbonyls from CO_(2)and ethylene by the combination of photocatalytic CO_(2)reduction and palladium-catalyzed coordination/insertion *** protocol provides an easy way to adjust the carbonyl content(from 0.13 to 12 mol%)and insertion selectivity(up to 99%isolated carbonyls)of the polyethylene copolymers,which enables the polymers tomaintain the main properties of highdensity polyethylene and simultaneously endows them with good *** addition,besides apolar polyethylene copolymers,polar-functionalized polyethylenes with in-chain isolated carbonyls can also be synthesized from CO_(2),ethylene and a polar monomer using the same *** believe our present work sheds new light on the synthesis of degradable polyethylenes by employing CO_(2)as a green carbonyl source.

关键词： carbon dioxide coordination polymerization polyethylene photoreduction photodegradation

Palladium-catalyzed stereoselective decarboxylative[4+2]cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones:Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones

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Chinese Chemical Letters 2024年第6期35卷 279-282页

作者： Ke Zhang Sheng Zuo Pengyuan You Tong Ru Fen-Er Chen Key Laboratory of natural Medicines of the Changbai Mountain Ministry of EducationCollege of PharmacyYanbian UniversityYanji 133002China College of Chemistry and Chemical Engineering Jiangxi Normal UniversityNanchang 330022China Engineering center of Catalysis and Synthesis for Chiral molecules Fudan UniversityShanghai 200433China Shanghai Engineering center of Industrial Catalysis for Chiral drugs Shanghai 200433China

A novel asymmetric[4+2]cycloaddition of 2-methylidenetrimethylene carbonate with pyrrolidonederived enones has been achieved to produce the functionalized tetrahydropyran-fused spirocyclic scaffolds via *** array of enantioenriched spiro-pyrrolidine-2,3-diones bearing adjacent quaternary and tertiary stereocenters are obtained in high yields with excellent enantioselectivities(up to 96% yield and 99% ee).The further transformation of the product has been accomplished for the construction of medical interesting β^(2,2)-amino acids and β-*** mechanistic research was well conducted.

关键词： Pyrrolidine-2,3-diones 2-Methylidenetrimethylene carbonate Asymmetric annulation Spiroheterocycles Allylic 1,3-strain

Encouraging Solution to the Problem of Synthesizing Protein α-Thioester

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Chinese Journal of Chemistry 2024年第10期42卷 1114-1120页

作者： Xinliang Liu Zijun Gao Jie Zhao Farong Ye Ping Huang Ping Wang center for Chemical Glycobiology Shanghai Key Laboratory for Molecular Engineering of Chiral DrugsFrontiers Science Center for Transformative MoleculesSchool of Chemistry and Chemical EngineeringZhangjiang Institute for Advanced StudyShanghai JiaoTongUniversityShanghai 200240China Shenzhen Research Institute of Shanghai Jiao Tong University ShenzhenGuangdong 518057China

Expressed protein ligation(EPL)provides a powerful tool to access large-size proteins with precise *** methods for constructing the critical protein thioester for EPL have predominantly relied on the recombinant intein fusion expressed in Escherichia coli(***).Despite its powerful applications,the expression of thioester derived from eukaryotic protein in *** inherently suffers from its limited solubility,the inactivity of intein,premature hydrolysis and low *** overcome these obstacles,we present herein the facile one-flask synthesis of inaccessible proteinα-thioester via a SUMO-protein-intein(SPI)sandwich *** utility of SUMO enhances the protein fusion yield and solubility,prevents premature hydrolysis and simplifies the purification *** inaccessible protein thioester with internal Cys residues can be readily produced and is compatible with the EPL-desulfurization protocol used to prepare complex proteins,which is otherwise difficult to obtain using traditional *** utility has been highlighted through the synthesis of human granulocyte colony-stimulating factor(G-CSF).

关键词： Desulfurization Glycoproteins Glycopeptides Protein expression Peptide thioester

Photo-induced 1,2-aryl migration of 2-chloro-1-arylpropanone under batch and flow conditions:Rapid,scalable and sustainable approach to 2-arylpropionic acids

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Chinese Chemical Letters 2024年第2期35卷 366-369页

作者： Qiao Li Minjie Liu Meifen Jiang Li Wan Yingtang Ning Fen-Er Chen College of Chemical Engineering Zhejiang University of TechnologyHangzhou 310014China Engineering center of Catalysis and Synthesis for Chiral molecules Fudan UniversityShanghai 200433China Shanghai Engineering center of Industrial Catalysis for Chiral drugs Shanghai 200433China Institute of Pharmaceutical Science and Technology Zhejiang University of TechnologyHangzhou 310014China

We report the photo-mediated 1,2-aryl migration of 2‑chloro-1-arylpropanones to 2-arylpropionic acids using HCOONa as an acid *** pragmatically focused study obviates the multiple-step sequence in the industrially employed,ZnO-promoted rearrangement strategy,and offers rapid access to various 2-arylpropionic acids under environmentally friendly ***,the successful transfer of this batch photochemistry to a continuous flow platform led to improved scalability and enabled the gram-scale synthesis of loxoprofen.

关键词： Green chemistry Flow chemistry 2-Arylpropionic acids Photo-Favorskii reaction

Nitrite-catalyzed economic and sustainable bromocyclization of tryptamines/tryptophols to access hexahydropyrrolo[2,3-b]indoles/tetrahydrofuroindolines in batch and flow

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Chinese Chemical Letters 2024年第7期35卷 247-252页

作者： Xiao Xiao Biao Chen Jia-Wei Li Jun-Bo Zheng Xu Wang Hang Zhao Fen-Er Chen Institute of Pharmaceutical Science and Technology Collaborative Innovation Center of Yangtze River Delta Region Green PharmaceuticalsZhejiang University of TechnologyHangzhou 310014China College of Chemistry and Chemical Engineering Jiangxi Normal UniversityNanchang 330022China Engineering center of Catalysis and Synthesis for Chiral molecules Department of ChemistryFudan UniversityShanghai 200433China Shanghai Engineering center of Industrial Asymmetric Catalysis for Chiral drugs Shanghai 200433China

A highly efficient and concise bromocyclization has been successfully achieved,in which tryptamine/tryptophol derivates can be transformed to valuable HPI/TFI scaffolds with economic and green ***,a controllable cascade transformation of bromocyclization and aromatic bromination has also been smoothly achieved to form dibrominated HPIs and *** could be successfully scaled up under both the batch process and a continuous flow *** most remarkable peculiarity of our process over all previous methods is that the generated water is the major ***,successful application of this new protocol has been demonstrated by the pharmaceutical and natural products syntheses.

关键词： Tryptamines and tryptophols Nitrite Economic and sustainable bromocyclization HPI and TFI structures Bath and flow

Spin chiral anisotropy of diamagnetic chiral mesostructured In_(2)O_(3)films

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Nano Research 2024年第8期17卷 7756-7761页

作者： Ting Ji Quanzheng Deng Hao Chen Lu Han Zhibei Qu Shunai Che Yingying Duan Frontiers Science center for Transformative molecules State Key Laboratory of Metal Matrix CompositesShanghai Key Laboratory for Molecular Engineering of Chiral DrugsSchool of Chemistry and Chemical EngineeringShanghai Jiao Tong UniversityShanghai 200240China School of Chemical Science and Engineering Tongji UniversityShanghai 200092China Department of Medicinal Chemistry School of PharmacyFudan UniversityShanghai 201203China

Spin chiral anisotropy(SChA)refers to the occurrence of different spin polarization in antipodal chiral ***,we report the SChA in diamagnetic chiral mesostructured In2O3 films(CMIFs)with manifestation of chirality-dependent magnetic circular dichroism(MCD)*** were grown on fluorine-doped tin dioxide conductive glass(FTO)substrates,which were synthesized via a hydrothermal route,with malic acid used as the symmetry-breaking *** levels of chirality have been identified in CMIFs:primary nanoflakes with atomically twisted crystal lattices and secondary helical stacking of the *** exhibit chirality-dependent asymmetric MCD signals due to the different interactions of chirality-induced effective magnetic field and external magnetic field,which distinguish from the commonly observed external magnetic fielddependent symmetric MCD *** findings provide insights into spin manipulation of spin-paired diamagnets.

关键词： chiral inorganics mesostructure diamagnet spin chiral anisotropy(SChA) magnetic circular dichroism(MCD)

Synergistic silver-mediated and palladium-catalyzed nondirected olefination of aryl C–H bond: quick access to multi-substituted aryl olefins

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Science China Chemistry 2024年第3期67卷 882-889页

作者： Jian Yao Lili Shao Xiaohong Huo Xiaoming Wang Shanghai Key Laboratory for Molecular Engineering of Chiral drugs Frontiers Science Center for Transformative MoleculesSchool of Chemistry and Chemical EngineeringShanghai Jiao Tong UniversityShanghai 200240China State Key Laboratory of Organometallic Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai 20032China School of Chemistry and Materials Science Hangzhou Institute for Advanced StudyUniversity of Chinese Academy of SciencesHangzhou 310024China

Transition metal-catalyzed olefination of aryl C-H bond is a powerful tool for the synthesis of alkenes. While the Pd-catalyzed oxidative C-H olefination of arenes, also known as Fujiwara-Moritani reaction, has been established as one of the most efficient methods, the substrates are largely limited to terminal olefins with electron-withdrawing group(s). Herein, we report a synergistic silver-mediated and palladium-catalyzed non-directed C-H olefination of arenes with vinyl(pseudo)halides, which offers a complementary strategy to the typical Fujiwara-Moritani reaction. The reactions proceeded well for a variety of halogenated arenes, heteroarenes, and olefin substrates, providing an efficient access to various multi-substituted aryl olefins, including trisubstituted/tetrasubstituted olefins and several complex olefins derived from medicines or natural products. Mechanistic studies indicated a bimetallic Pd/Ag cooperation is operative in the catalysis, i.e., the reaction is initiated by aryl C-H bond cleavage via ligation with phosphine/Ag species, followed by transferring of the aryl moiety to a vinyl palladium intermediate,which is in turn formed by oxidative addition of vinyl(pseudo)halide to a Pd complex. This method enables the synthesis of a wide range of challenging multi-substituted vinyl products from simple arenes(directing-group free) in a streamlined and controllable fashion.

关键词： direct C–H olefination multi-substituted aryl alkenes bimetallic Pd/Ag cooperation C–H functionalization

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Visible light cross-linking and bioactive peptides loaded integrated hydrogel with sequential release to accelerate wound healing complicated by bacterial infection

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Nano Research 2024年第3期17卷 1737-1747页

作者： Guiyan Wang Ning Yuan Jun Zhang Man Qin Suwei Dong Yuguang Wang Department of Pediatric Dentistry Peking University School and Hospital of StomatologyBeijing 100081China State Key Laboratory of natural and Biomimetic drugs Chemical Biology Centerand School of Pharmaceutical SciencesPeking UniversityBeijing 100191China Department of Prosthodontics Peking University School and Hospital of StomatologyBeijing 100081China

The effective management of bacterial infections that are resistant to multiple drugs remains a substantial clinical *** eradication of drug-resistant bacteria and subsequent promotion of angiogenesis are imperative for the regeneration of the infected ***,a novel and facile peptide containing injectable hydrogel with sustained antibacterial and angiogenic capabilities is *** antibacterial peptide that consists of 11 residues(CM11,WKLFKKILKVL)is loaded onto acrylate-modified gelatin through charge interactions.A vascular endothelial growth factor mimetic peptide KLT(KLTWQELYQLKYKGI)with a GCG(Gly-Cys-Gly)modification at the N-terminal is covalently coupled through a visible light-induced thiol-ene *** this reaction,the acrylate gelatin undergoes cross-linkage within *** on the physical/chemical double crosslinking strategy,the bioactive peptides achieve sustained and sequential *** results show that the hydrogel significantly inhibits methicillin-resistant Staphylococcus aureus(MRSA)growth through the rapid release of CM11 peptides at early stage;it forms obvious growth inhibition zones against pathogenic bacterial ***,cell counting kit-8 assay and scratch test confirm that the CM11/KLT-functionalized hydrogels promote cell proliferation and migration through the later release of KLT *** a mouse skin wound infected with self-luminous MRSA,the CM11/KLT-functionalized hydrogels enhance wound healing,with rapidly bacterial infection reduction,lower expression of inflammatory factors,and neovascularization *** results suggest that the rationally designed,sustained and sequential release CM11/KLT-functionalized hydrogels have huge potential in promoting the healing of multi-drug resistant bacterial infected wounds.

关键词： antimicrobial peptide vascular endothelial growth factor(VEGF)mimetic peptide sequential release visible-light crosslinking hydrogel wound therapy

Semisynthesis of homogeneous spike RBD glycoforms from SARS-CoV-2 for profiling the correlations between glycan composition and function

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National Science Review 2024年第2期11卷 145-154页

作者： Farong Ye Cheng Li Feng-Liang Liu Xinliang Liu Peng Xu Rong-Hua Luo Wenping Song Yong-Tang Zheng Tianlei Ying Biao Yu Ping Wang center for Chemical Glycobiology Frontiers Science Center for Transformative Molecules Zhangjiang Institute for Advanced Study School of Chemistry and Chemical Engineering Shanghai Jiao Tong University MOE/NHC/CAMS Key Laboratory of Medical Molecular Virology Shanghai Frontiers Science Center of Pathogenic Microorganisms and Infection Shanghai Institute of Infectious Disease and BiosecurityShanghai Engineering Research Center for Synthetic ImmunologySchool of Basic Medical Sciences Shanghai Medical College Fudan University Key Laboratory of Animal Models and Human Disease Mechanisms of Chinese Academy of Sciences/Key Laboratory of bioactive Peptides of Yunnan Province Center for Biosafety Mega-Science Kunming Institute of ZoologyChinese Academy of Sciences State Key Laboratory of Bioorganic and natural Products Chemistry Center for Excellence in Molecular Synthesis Shanghai Institute of Organic Chemistry Chinese Academy of Sciences Shenzhen Research Institute of Shanghai Jiao Tong University

Vaccines have been the primary remedy in the global fight against coronavirus disease 2019（COVID-19）.The receptor-binding domain（RBD） of the spike protein, a critical viral immunogen, is affected by the heterogeneity of its glycan structures and relatively low immunogenicity. Here, we describe a scalable synthetic platform that enables the precise synthesis of homogeneously glycosylated RBD, facilitating the elucidation of carbohydrate structure–function relationships. Five homogeneously glycosylated RBDs bearing biantennary glycans were prepared, three of which were conjugated to T-helper epitope(Tpep) from tetanus toxoid to improve their weak immune response. Relative to natural HEK293-derived RBD, synthetic RBDs with biantennary N-glycan elicited a higher level of neutralising antibodies against SARS-CoV-2 in mice. Furthermore, RBDs containing Tpepelicited significant immune responses in transgenic mice expressing human angiotensin-converting enzyme 2. Our collective data suggest that trimming the N-glycans and Tpepconjugation of RBD could potentially serve as an effective strategy for developing subunit vaccines providing efficient protection.

关键词： peptide ligation glycosylation glycoprotein