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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

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糖基化干扰素-γ的半合成

有机化学 2024年第7期44卷 2296-2304页

作者：周敏园赵洁叶发荣黄平邓明刚王平华中农业大学生命科学与技术学院上海交通大学张江高等研究院上海手性药物分子工程重点实验室化学糖生物学中心

干扰素-γ(IFN-γ)是一种重要的细胞因子,具有增强免疫活性、抗肿瘤和抗病毒的作用,在医学研究和临床应用中具有广泛的潜力.本研究报道了一种均一N-Glc NAc修饰的IFN-γ的化学半合成方法.利用化学方法合成制备糖肽片段(Pyr1-Leu33)和多... 详细信息

干扰素-γ(IFN-γ)是一种重要的细胞因子,具有增强免疫活性、抗肿瘤和抗病毒的作用,在医学研究和临床应用中具有广泛的潜力.本研究报道了一种均一N-Glc NAc修饰的IFN-γ的化学半合成方法.利用化学方法合成制备糖肽片段(Pyr1-Leu33)和多肽片段(Lys34-Ser39),并通过大肠杆菌表达得到多肽片段(Ser40-Gly138).采用“表达丝氨酸连接”和“自然化学连接-脱硫”相结合的策略,成功完成了自C端到N端的N-Glc NAc修饰的IFN-γ蛋白的合成,并成功地对目标糖蛋白进行了复性.

关键词：自然化学连接表达丝氨酸连接 β-硫代氨基酸糖基化修饰

Revealing Functional Significance of Interleukin-2 Glycopro-teoforms Enabled by Expressed Serine Ligation

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Chinese Journal of Chemistry 2022年第7期40卷 787-793页

作者： Jie Zhao Jiazhi Liu Xinnan Liu Qi Cao Hongbo Zhao Lizhen Liu farong ye Can Wang Hong Shao Dongxiang Xue Houchao Tao Bin Li Biao Yu Ping Wang Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs School of Chemistry and Chemical EngineeringShanghai Jiao Tong University800 Dongchuan RoadShanghai 200240China Shanghai Institute of Immunology Department of Immunology and MicrobiologyShanghai Jiao Tong University School of Medicine280 S.Chongqing RoadShanghai 200025China Obstetrics and Gynecology Hospital of Fudan University Shanghai 200011China Shanghai Institute for Food and Drug Control NMPA Key Laboratory for Quality Control of Therapeutic Monoclonal AntibodiesShanghai 201203China iHuman Institute ShanghaiTech UniversityHaike Road 230Shanghai 200032China State Key Laboratory of Bioorganic and Natural Products Chemistry Center for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryChinese Academy of Sciences345 Lingling RoadShanghai 200032

Naturally occurring interleukin-2(IL-2)is a pleiotropic glycoprotein that regulates immune responses by controlling the differentia-tion and homeostasis of T ***-glycosylated IL-2 has been used in clinical settings for three ***,the function of the O-glycan of native IL-2 remains ***,to stress this issue,we report a highly efficient semi-synthesis of homogeneous glycosylated IL-2 with various glycoproteoforms on a multi-milligram *** glycopeptide fragment was prepared by chemical synthesis and then merged with recombinant fragment via a serine ligation to generate the desired glycoprotein in a single *** evaluation of the homogenous glycoprotein library reveals that the activity of IL-2 in activating individual T cell subset is glycan dependent,thus highlighting the possibility of further improving current clinical medicine.

关键词： Oligosaccharide Glycoprotein Serine ligation Interleukin-2 Glycopeptides

Histidine-Specific Peptide Modification via Visible-Light-Promoted C-H Alkylation

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Histidine-Specific Peptide Modification via Visible-Light-Pr...

A strategy for enhanced tumor targeting of photodynamic therapy based on Escherichia coli-driven drug delivery system

中国化学会第八届天然产物全合成青年学术研讨会

作者： Xiaoping Chen farong ye Xiaosheng Luo Xueyi Liu Jie Zhao Siyao Wang Qingqing Zhou Gong Chen 王平 Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs School of Chemistry and Chemical Engineering Shanghai Jiao Tong University State Key Laboratory and Institute of Elemento-Organic Chemistry College of Chemistry Nankai University

＜正＞Histidine（His） carries a unique heteroaromatic imidazole side chain and plays irreplaceable functional roles in peptides and proteins. Existing strategies for siteselective histidine modification predominantly rely on the N-substitution reactions of the moderately nucleophilic imidazole group, which inherently suffers from the interferences from lysine and cysteine residues. Chemoselective modification of histidine remain one of the most difficult challenges in peptide chemistry.

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Science China Materials 2021年第1期64卷 232-240页

作者： Tao Dai farong ye Ping Hu Xiaohong Pan Jincan Chen Yunmei Huang Huanhuan Wang Lei Zhang Mingdong Huang Jianyong Liu Jianqiang Su Xueyuan Chen Zhuo Chen State Key Laboratory of Structural Chemistry CAS Key Laboratory of Design and Assembly of Functional NanostructuresFujian Institute of Research on the Structure of MatterChinese Academy of SciencesFuzhou350002China College of Chemistry Fuzhou UniversityFuzhou350116China Academy of Integrative Medicine Fujian University of Traditional Chinese MedicineFuzhou350122China Key Lab of Urban Environment and Health Institute of Urban EnvironmentChinese Academy of SciencesXiamen361021China University of Chinese Academy of Sciences Beijing100049China

Escherichia coli(E. coli) DH5α has been recognized as a non-pathogenic bacterial strain with tumor colonization ability. However, whether such a bacteria-driven drug-delivery system can improve the targeting of tumor therapy or not remains essentially untouched. Herein, a series of zinc phthalocyanine(ZnPc) photosensitizers with different numbers of charges were prepared and their electrostatic adhesion properties on E. coli were investigated via measuring their fluorescence intensities by flow cytometer. Among these ZnPc photosensitizers investigated, the ZnPc conjugate with four positive charges(named ZnPc-IR710) exhibited the highest loading capacity and the best fluorescence imaging performance of E. coli. With the help of E. coli, E. coli@ZnPcIR710 presented a significantly enhanced cytotoxicity on human breast cancer MCF-7 cells compared with ZnPc-IR710(survival rate of tumor cells was 39% vs. 57% at a concentration of 50 nmol L-1). Moreover, in vivo study showed that E. coli@ZnPc-IR710 remarkably inhibited the tumor growth and resulted in a complete tumor growth suppress in subcutaneous mouse 4T1 breast tumor model. These results demonstrated the great promise of bacterial-guided photodynamic therapy(PDT) in the treatment of solid tumors, and provide a unique strategy to enhance the antitumor efficacy of PDT by utilizing bacterial vectors in tumors.

关键词： photosensitizer zinc phthalocyanine bacteria-driven drug delivery system E.coli DH5α fluorescent molecular tomography

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Corrosion Behavior of Commercial Magnetic Refrigerant Gadolinium in Water

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Journal of Rare Earths 2004年第Z1期22卷 99-102页

作者： Zhang Zeyu Long Yi Wen Da ye Rongchang Wan farong School of Materials Science and Engineering University of Science and Technology Beijing Beijing 100083China

Gadolinium(Gd) used as magnetic refrigerant always works in water ***, its poor corrosion resistance is serious impediment against wider application of *** this paper, the corrosion behavior of two types of commercial Gd ( A, B both are 98.9 at.% pure) with the same oxygen content has been *** results show that the corrosion rate of A is 3.226 times higher than that of B in deionized water and 6.039 times in tap *** to SEM, the different corrosion rate is because of the different distribution of impurity in *** addition,NaOH solution was chosen as inhibitor to prevent Gd from being corroded *** pitting corrosion and weight loss were observed for commercial Gd even after immersion for nearly 2000 h in NaOH solution.

关键词： gadolinium corrosion behavior impurity pitting corrosion

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水城红阳猕猴桃果实生长发育规律

贵州农业科学 2017年第11期45卷 89-92页

作者：叶发荣李秀亚肖钧宋福兵莫庆忠周玉萍六盘水市农业科学研究院贵州六盘水553000

为栽培优质丰产的猕猴桃提供参考,以3年生红阳猕猴桃(Actinidia chinensis)为试材,定期测量猕猴桃果实的纵径、横径、鲜果重及体积的变化,探明果实的动态生长发育规律。结果表明:红阳猕猴桃果实纵横径经历快速生长-缓慢生长-停滞生长的... 详细信息

为栽培优质丰产的猕猴桃提供参考,以3年生红阳猕猴桃(Actinidia chinensis)为试材,定期测量猕猴桃果实的纵径、横径、鲜果重及体积的变化,探明果实的动态生长发育规律。结果表明:红阳猕猴桃果实纵横径经历快速生长-缓慢生长-停滞生长的变化规律,呈现逐渐上升的单曲线;果实鲜重和体积呈现双S形生长曲线,表现为缓慢生长-快速生长-缓慢生长-快速生长-停滞生长;果实纵径净增长曲线在授粉后15d(4月20日)出现1个生长高峰,果实横径净增长有3个生长高峰,分别出现在授粉后15d(4月20日)、35d(5月10日)和98d(7月12日);果实鲜重净生长量有3个生长高峰,分别出现在授粉后35d(5月10日)、55d(5月30日)和138d(8月22日),果实体积净生长量有2个生长高峰,分别出现在授粉后35d(5月10日)和67d(6月11日)。

关键词：红阳猕猴桃果实纵横径鲜果重体积

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基于足细胞保护探讨黄芪甲苷改善糖尿病肾病的研究进展

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中医药信息 2024年第7期41卷 61-67页

作者：柳成张钧清王世涛石晶叶莉莹李颖颖张法荣山东中医药大学山东济南250014 黑龙江中医药大学佳木斯学院黑龙江佳木斯154007 广饶县中医院山东东营257300 山东中医药大学附属医院山东济南250014

糖尿病肾病(DKD)是由糖尿病引发的肾脏微血管病变。足细胞是肾脏固有细胞中高度分化的上皮细胞类型之一,是维持肾小球滤过膜屏障通透性、完整性的重要组分。本文基于足细胞的病理和生理学特点,重点探讨黄芪甲苷(AS-Ⅳ)改善糖脂代谢紊乱... 详细信息

糖尿病肾病(DKD)是由糖尿病引发的肾脏微血管病变。足细胞是肾脏固有细胞中高度分化的上皮细胞类型之一,是维持肾小球滤过膜屏障通透性、完整性的重要组分。本文基于足细胞的病理和生理学特点,重点探讨黄芪甲苷(AS-Ⅳ)改善糖脂代谢紊乱诱导DKD足细胞凋亡、足细胞黏附障碍、足细胞分化、足细胞炎症、足细胞线粒体功能障碍和足细胞氧化应激的作用机制,发现AS-Ⅳ可介导CaN/NFAT、TUG1/TRAF5、miR-378/TRAF5、PPARγ/Klotho/FoxO1、p38-MAPK、PERK/ATF4/CHOP、ATF6、IRE1/JNK、Notch、AMPK/MTOR/p70S6K、ILK、Wnt/β-catenin、TGF-β1/Smads、NLRP3/Caspase-1/IL-1β、NF-κB、Sirt1/p53/Drpl、Nrf2/PINK1、Nrf2/ARE/TFAM和GSK-3β/Nrf2/HO-1等多种级联途径,恢复足细胞状态,有效延缓DKD的进展。

关键词：糖尿病肾病足细胞糖脂代谢紊乱黄芪甲苷研究进展

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The interaction between polyphyllin I and SQLE protein induces hepatotoxicity through SREBP-2/HMGCR/SQLE/LSS pathway

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Journal of Pharmaceutical Analysis 2023年第1期13卷 39-54页

作者： Zhiqi Li Qiqi Fan Meilin Chen Ying Dong farong Li Mingshuang Wang Yulin Gu Simin Guo Xianwen ye Jiarui Wu Shengyun Dai Ruichao Lin Chongjun Zhao Beijing Key Laboratory for Quality Evaluation of Chinese Materia Medica School of Chinese Materia MedicaBeijing University of Chinese MedicineBeijing100029China Key Laboratory of Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry National Engineering Laboratory for Resource Developing of Endangered Chinese Crude Drugs in Northwest of ChinaShaanxi Normal UniversityXi'an710119China National Institutes for Food and Drug Control Beijing102629China

Polyphyllin I(PPI)and polyphyllin II(PII)are the main active substances in the Paris ***,liver toxicity of these compounds has impeded their clinical application and the potential hepatotoxicity mechanisms remain to be *** this work,we found that PPI and PII exposure could induce significant hepatotoxicity in human liver cell line L-02 and zebrafish in a dose-dependent *** results of the proteomic analysis in L-02 cells and transcriptome in zebrafish indicated that the hepatotoxicity of PPI and PII was associated with the cholesterol biosynthetic pathway disorders,which were alleviated by the cholesterol biosynthesis inhibitor ***,3-hydroxy-3-methy-lglutaryl CoA reductase(HMGCR)and squalene epoxidase(SQLE),the two rate-limiting enzymes in the cholesterol synthesis,selected as the potential targets,were confirmed by the molecular docking,the overexpression,and knockdown of HMGCR or SQLE with ***,the pull-down and surface plasmon resonance technology revealed that PPI could directly bind with SQLE but not with ***,these data demonstrated that PPI-induced hepatotoxicity resulted from the direct binding with SQLE protein and impaired the sterol-regulatory element binding protein 2/HMGCR/SQLE/lanosterol synthase pathways,thus disturbing the cholesterol biosynthesis *** findings of this research can contribute to a better understanding of the key role of SQLE as a potential target in drug-induced hepatotoxicity and provide a therapeutic strategy for the prevention of drug toxic effects with similar structures in the future.

关键词： Polyphyllin I Polyphyllin II Zebrafish Hepatotoxicity SQLE