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Utilization of hydralazine as a reactive matrix for enhanced detection and on-MALDI-target derivatization of saccharides

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Chinese Chemical Letters 2024年第5期35卷 386-391页

作者： Dan Ouyang Huan Huang Yanting He Jiajing Chen Jiali Lin Zhuling Chen Zongwei Cai Zian Lin Ministry of Education key laboratory of analytical Science for Food Safety and Biology Fujian Provincial Key Laboratory of Analysis and Detection Technology for Food SafetyCollege of ChemistryFuzhou UniversityFuzhou 350108China School of Pharmacy Bengbu Medical UniversityBengbu 233000China Partner state key laboratory of Environmental and Biological Analysis Department of ChemistryHong Kong Baptist UniversityHong KongChina

Saccharides are a sort of ubiquitous and vital molecules within the whole ***,the application of saccharides analysis with matrix-assisted laser desorption/ionization mass spectrometry(MALDI-MS)is restricted by their low ionization efficiency and the instability of the sialic acid *** strategy based on nonreductive amination provides a good solution,however,this is often time consuming and may result in sample loss due to removal of excessive derivatization ***,hydralazine(HZN)was utilized as a reactive matrix for labeling reducing saccharides directly on MALDI target which eliminated tedious sample preparation and avoided sample *** optimization,effective and reproducible on-MALDI-target derivatization of neutral and acidic saccharides was achieved in both positive and negative *** with 2,5-dihydroxybenzoic acid(DHB)and 9-aminoacridine(9-AA),HZN improved the detection sensitivity of reducing saccharides and provided more abundant fragment ions in MS/MS ***,26 kinds of neutral glycans and 5 kinds of sialic glycans were identified from ovalbumin(OVA)and bovine fetuin,*** with the statistical models,this strategy could be used to distinguish and predict samples of 6 brands of beer,and discriminate 2 kinds of beer fermentation *** addition,HZN was applied for quantitative analysis of glucose in urine samples,and the obtained urine glucose concentrations of diabetic patients were consistent with the clinical test results,showing the potential of qualitative and quantitative analysis of reducing saccharides in complex samples.

关键词： Hydralazine Reactive matrix On-MALDI-target derivatization Saccharides

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Visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO_(2)

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Chinese Chemical Letters 2024年第7期35卷 281-284页

作者： Tian-Yu Gao Xiao-Yan Mo Shu-Rong Zhang Yuan-Xu Jiang Shu-Ping Luo Jian-Heng Ye Da-Gang Yu key laboratory of Green chemistry&Technology of Ministry of Education College of ChemistrySichuan UniversityChengdu 610064China state key laboratory Breeding Base of Green chemistry-Synthesis Technology Zhejiang University of TechnologyHangzhou 310014China state key laboratory of Elemento-Organic chemistry Nankai UniversityTianjin 300071China

Herein, we report the first visible-light photoredox-catalyzed carboxylation of aryl epoxides with CO_(2)to synthesize hydroxy acid derivatives. A variety of valuable β-, γ-, δ-, ε–hydroxy acid derivatives are obtained in moderate to high yields under mild conditions. This protocol shows noteworthy functionalgroup compatibility, high chemo-and regioselectivities under transition-metal-free conditions with an inexpensive organo-dye as photosensitizer. Mechanistic studies indicate that the benzylic carbanion is generated as an intermediate via the sequential single electron transfer(SSET) process.

关键词： Carbon dioxide Epoxides Visible-light photoredox catalysis Hydroxy acid Sequential single electron transfer

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Genome mining of sulfonated lanthipeptides reveals unique cyclic peptide sulfotransferases

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Acta Pharmaceutica Sinica B 2024年第6期14卷 2773-2785页

作者： Meng Wang Wen-Wei Li Zhe Cao Jianong Sun Jiang Xiong Si-Qin Tao Tinghong Lv Kun Gao Shangwen Luo Shi-Hui Dong state key laboratory of Applied Organic chemistry College of Chemistry and Chemical EngineeringLanzhou UniversityLanzhou 730000China

Although sulfonation plays crucial roles in various biological processes and is frequently utilized in medicinal chemistry to improve water solubility and chemical diversity of drug leads,it is rare and underexplored in ribosomally synthesized and post-translationally modified peptides(RiPPs).Biosynthesis of RiPPs typically entails modification of hydrophilic residues,which substantially increases their chemical stability and bioactivity,albeit at the expense of reducing water *** explore sulfonated RiPPs that may have improved solubility,we conducted co-occurrence analysis of RiPP class-defining enzymes and sulfotransferase(ST),and discovered two distinctive biosynthetic gene clusters(BGCs)encoding both lanthipeptide synthetase(LanM)and *** expressing these BGCs,we characterized the structures of novel sulfonated lanthipeptides and determined the catalytic details of LanM and *** demonstrate that SslST-catalyzed sulfonation is leader-independent but relies on the presence of A ring formed by *** LanM and ST are promiscuous towards residues in the A ring,but ST displays strict regioselectivity toward *** recognition of cyclic peptide by ST was further *** evaluation underscores the significance of the ST-catalyzed *** study sets up the starting point to engineering the novel lanthipeptide STs as biocatalysts for hydrophobic lanthipeptides improvement.

关键词： Lanthipeptides Sulfotransferases Sulfonation Biosynthesis Genome mining

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Application of "Three-in-One" Strategy Based on MOF-199 in Determination of Phenylenediamine Isomers and Cr(Ⅵ)

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Journal of Analysis and Testing 2024年第1期8卷 28-39页

作者： Yueci Xiang Jiantao Wei Huipeng Sun Ruiyi Zhao Zehua Han Shuangtong Wu Xiaoyan Liu Haixia Zhang state key laboratory of Applied Organic chemistry and College of chemistry and Chemical Engineering Lanzhou UniversityLanzhou 730000China

Industry progressing caused the pollutants into the surface and groundwater,including organic pollutants such as phenylenediamine(PD)and heavy metals such as Cr(Ⅵ).Herein,a simple"three-in-one"strategy based on MOF-199 was *** MOF-199 catalytic system could be used for the rapid detection of Cr(Ⅵ)and o-phenylenediamine(OPD)in linear ranges of 0.5-50.0μmol/L and 7.0-250.0μmol/L,with the limits of detection of 0.1 and 0.5μmol/L,*** method can also efficiently discriminate PD isomers in just 15 ***,Cr(Ⅵ)was reduced to Cr(Ⅲ)and the elimination of OPD was carried *** simple synthesis,high sensitivity,easy operation,and low cost,this method presented a potential platform for on-site detection of pollutants in water samples.

关键词： On-site detection “Three-in-one”strategy Phenylenediamine isomers

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The structure-directing role of heterologous seeds in the synthesis of zeolite

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Green Energy & Environment 2024年第5期9卷 792-801页

作者： Haoyang Zhang Binyu Wang Wenfu Yan state key laboratory of Inorganic Synthesis&Preparative chemistry College of ChemistryJilin UniversityChangchun130012China

Zeolites have been widely used as catalysts,ion-exchangers,and adsorbents in chemical industries,detergent industry,steel industry,glass industry,ceramic industry,medical and healthﬁeld,and environmentalﬁeld,and recently applied in energy ***-assisted synthesis is a very effective approach in promoting the crystallization of *** some cases,the target zeolite cannot be formed in the absence of seed *** homologous seed-assisted synthesis,the structure of the seed zeolite is the same to that of the target zeolite,while the structure of the seed zeolite is different to that of the target zeolite in the heterologous seed-assisted *** this review,we brieﬂy summarized the heterologous seed-assisted syntheses of zeolites and analyzed the structure-directing effect of heterologous seeds and surveyed the“common composite building units(CBUs)hypothesis”and the“common secondary building units(SBUs)hypothesis”.However,both hypotheses cannot explain all observations on the heterologous seed-assisted ***,we proposed that the formation of the target zeolite does need nuclei with the structure of target zeolite and the formation of the nuclei of the target zeolite can be promoted by either the undissolved seed crystals with the same CBUs or SBUs to the target zeolite or by the facilitated appropriate distribution of the speciﬁc building units due to the presence of the heterologous seed that does not have any common CBUs and SBUs with the target zeolite.

关键词： Zeolite Heterologous seed Synthesis Structure-directing effect

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Electrochemical chemoselective thiocarbamylation of late-stage Tyr-containing drugs and peptides

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Science China chemistry 2024年

作者： Wan-Jie Wei Xin-Yu Wang Hai-Tao Tang Fei-Hu Cui Yun-Qi Wu Ying-Ming Pan state key laboratory for chemistry and Molecular Engineering of Medicinal Resources Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China) Collaborative Innovation Center for Guangxi Ethnic Medicine School of Chemistry and Pharmaceutical Sciences Guangxi Normal University

The synthesis and modification of peptides occupy a unique position in the field of drug development, and the functionalization of amino acids is a valuable strategy as an alternative to peptide modification. Currently, the development of tyrosine(Tyr) as a target amino acid is a major challenge in the field of chemistry. Herein, we report an electrochemical radical coupling reaction of labeling tyrosine-containing active drugs and peptides with thiocarbamate derivatives for the first time. This tri-component, onepot reaction can be performed smoothly under simple, gentle, and clean electrochemical conditions and is suitable for the functionalization of various Tyr-containing drug molecular derivatives and peptides.

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Living/controlled polymerization of vinylpyridines into sequence-regulated copolymers by Lewis pair

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Science China chemistry 2024年第8期67卷 2737-2746页

作者： Qiankun Ding Wuchao Zhao Fukuan Li Jianghua He Yuetao Zhang Department of state key laboratory of Supramolecular Structure and Materials College of ChemistryJilin UniversityChangchun 130012China

The poly(vinylpyridine)(PVP) based(co)polymers are of particular interest in materials science, due to their multifunctionality and diverse applications. So far, there is no report on the sequence-regulated copolymerization of vinylpyridines(VPs) and methacrylate monomer in one-step manner yet. Here we designed and synthesized a series of guanidine phosphines as Lewis base(LB), which is combined with bulky organoaluminium to construct Lewis pairs(LPs) for polymerization of VPs. The living/controlled polymerization of 4-vinylpyridine(4-VP) or 2-vinylpyridine(2-VP) can be accomplished with remarkable efficiency by such Lewis pair polymerization(LPP), furnishing polymers with high molecular weight(up to 288 kg/mol) and narrow molecular weight distribution(as low as 1.17). Mechanistic studies reveal the interaction of LPs and formation of zwitterionic intermediates, providing solid evidences to support the proposed polymerization mechanism. More importantly, by simply adjusting the LA dosage, this LPP strategy realizes the unprecedented control over the sequence regulation of 2-VP-based copolymers from gradient to block in one-step manner, regardless of the monomer ratio, which greatly expands the versatility of the LPP.

关键词： guanidine phosphine Lewis pair polymerization living/controlled polymerization vinyl pyridine sequence regulation

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Hydrodechlorination of trifluoro-trichloroethane to chlorotrifluoroethylene:Revealing the deactivation mechanism and regeneration strategy of Pd-Cu/AC catalyst

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Chinese Journal of Chemical Engineering 2024年第6期70卷 261-268页

作者： Song Tian Yicheng Chen Xiaoyu Wen Bingcheng Li Jian Lu Zile Li Feng Feng Qingtao Wang Qunfeng Zhang Xiaonian Li state key laboratory Breeding Base of Green chemistry Synthesis Technology Institute of Industrial Catalysis of Zhejiang University of TechnologyHangzhou 310014China state key laboratory of Fluorine&Nitrogen Chemicals Xi'an Modern Chemistry Research InstituteXi'an 710065China

Chlorotrifluoroethylene(CTFE)is a vital fluorinated olefinic monomer produced through the catalytic hydrodechlorination of trichlorotrifluoroethane(CFC-113),an eco-friendly ***,hydrodechlorination catalysts for olefin production often suffer from poor *** Pd/AC catalyst and Pd-Cu/AC catalyst prepared by co-impregnation method exhibited poor stability,Pd-Cu/AC catalyst with CFC-113 conversion dropping to around 37%after 50 h of hydrodechlorination ***-Emmett-Teller,transmission electron microscopy,X-ray photoelectron spectroscopy,and X-ray diffraction of fresh and deactivated Pd/AC catalysts indicate that the deactivation of Pd/AC catalysts is due to high-temperature agglomeration of *** analysis of fresh and deactivated Pd-Cu/AC catalysts using Brunauer-Emmett-Teller,transmission electron microscopy,and thermogravimetric analysis techniques revealed decreased dispersion of active sites,reduced surface area,catalyst aggregation deactivation,and a significant decrease in Cu ***,the results of NH3-TPD revealed that the acid sites of the catalyst increased significantly.X-ray diffraction spectra indicated the formation of new species,basic copper chloride(Cu_(2)(OH)_(3)Cl),during the *** the reaction progressed,these new species agglomerated,leading to a gradual loss of catalyst ***,the deactivated catalyst was successfully reactivated using a simple alkaline washing method.

关键词： CFC-113 Hydrodechlorination Chlorotrifluoroethylene Catalyst deactivation

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Supramolecular systems for bioapplications:recent research progress in China

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Science China chemistry 2024年第5期67卷 1397-1441页

作者： Yue-Yang Liu Xiao-Yong Yu Yu-Chen Pan Hang Yin Shuang Chao Yujie Li He Ma Minzan Zuo Kun-Xu Teng Jun-Li Hou Yong Chen Dong-Sheng Guo Ruibing Wang Yuxin Pei Zhichao Pei Jiang-Fei Xu Xiao-Yu Hu Chunju Li Qing-Zheng Yang Leyong Wang Yu Liu Zhan-Ting Li state key laboratory of Organometallic chemistry Key Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional MoleculesShanghai Institute of Organic ChemistryChinese Academy of SciencesUniversity of Chinese Academy of SciencesShanghai 200032China Department of chemistry Fudan UniversityShanghai 200438China College of chemistry State Key Laboratory of Elemento-Organic ChemistryCollaborative Innovation Center of Chemical Science and EngineeringNankai UniversityTianjin 300071China state key laboratory of Quality Research in Chinese Medicine Institute of Chinese Medical SciencesUniversity of MacaoMacao 999078China College of chemistry&Pharmacy Northwest A&F UniversityYangling 712100China key Lab of Organic Optoelectronics&Molecular Engineering Department of ChemistryTsinghua UniversityBeijing 100084China College of Materials Science and Technology Nanjing University of Aeronautics and AstronauticsNanjing 211106China key laboratory of Radiopharmaceuticals Ministry of EducationCollege of ChemistryBeijing Normal UniversityBeijing 100875China Tianjin key laboratory of Structure and Performance for Functional Molecules College of ChemistryTianjin Normal UniversityTianjin 300387China state key laboratory of analytical chemistry for Life Science Jiangsu Key Laboratory of Advanced Organic MaterialsSchool of Chemistry and Chemical EngineeringNanjing UniversityNanjing 210023China

Supramolecular systems feature dynamic,reversible and stimuli-responsive characteristics,which are not easily achieved by molecular *** last decade has witnessed tremendous advances in the investigations of supramolecular systems for various bioapplications,which include drug delivery,anticancer therapy,antibacterial therapy,photodynamic therapy,photothermal therapy,combination therapy,antidotes for residual drugs or toxins,and bioimaging and ***-guest chemistry has played a key role in the development of such bioactive supramolecular systems,and natural macrocycles(such as cyclodextrins),synthetic macrocycles(such as calixarenes,cucurbit[n]urils,and pillararenes),and porous framework polymers(such as supramolecular organic frameworks and flexible organic frameworks)have been most successfully used as hosts to build different kinds of host-guest systems for attaining designed *** self-assembly of rationally designed amphiphilic molecules,macromolecules and polymers represent another important approach for the construction of supramolecular architectures with advanced *** this review,we summarize the important contributions made by Chinese researchers in this field,with emphasis on those reported in the past five years.

关键词： host-guest chemistry drug delivery anticancer and antibacterial photodynamic therapy photothermal therapy antidote transmembrane channel bioimaging and biosensing

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Establishment of microneurovascular units in alginate hydrogel microspheres to reveal the anti-hypoxic effect of salidroside

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Journal of Pharmaceutical Analysis 2024年第6期14卷 926-929页

作者： Shiyu Chen Yuxuan Li Yingrui Zhang Hongren Yao Tong Xu Yi Zhang Jin-Ming Lin Xian-Li Meng state key laboratory of Southwestern Chinese Medicine Resources Innovative Institute of Chinese Medicine and PharmacyChengdu University of Traditional Chinese MedicineChengdu611137China Beijing key laboratory of Microanalytical Methods and Instrumentation Department of ChemistryKey Laboratory of Bioorganic Phosphorus Chemistry&Chemical Biology(Ministry of Education)Tsinghua UniversityBeijing100084China School of ethnic Medicine Chengdu University of Traditional Chinese MedicineChengdu611137China

Microneurovascular units(mNVUs),comprising neurons,micro-glia,and blood-brain barrier(BBB)endothelial cells,are pivotal to the central nervous system and are associated with cerebral hypoxia and brain *** hypoxia triggers microglial overactivity,causing inflammation,neuronal injury,and disruption of the BBB[1].Salidroside(Sal),a key compound in Tibetan medicine Rhodiola crenulata,mitigates hypoxia-induced metabolic disorders and neuronal damage by preserving mitochondrial function[2].

关键词： injuries preserving Tibetan

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