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Mechanism of TMB Discoloration Catalyzed by Layered CoNi@CN Nanozymes: Application Based on Smart Phone for Resorcinol Detection
IF 5.5 1区 化学
Chinese Journal of Chemistry Pub Date : 2024-10-25 DOI: 10.1002/cjoc.202400841
Qingyong Guo, Rongsheng Xiao, Haifeng Chen, Meishuo Bao, Jingwen Qi, Qian-qian Jia, Wuxiang Zhang
{"title":"Mechanism of TMB Discoloration Catalyzed by Layered CoNi@CN Nanozymes: Application Based on Smart Phone for Resorcinol Detection","authors":"Qingyong Guo,&nbsp;Rongsheng Xiao,&nbsp;Haifeng Chen,&nbsp;Meishuo Bao,&nbsp;Jingwen Qi,&nbsp;Qian-qian Jia,&nbsp;Wuxiang Zhang","doi":"10.1002/cjoc.202400841","DOIUrl":"https://doi.org/10.1002/cjoc.202400841","url":null,"abstract":"<div>\u0000 \u0000 <p>Real-time on-site monitoring of resorcinol (RS) concentrations is crucial for detecting hazardous levels, enabling prompt response measures to mitigate potential environmental and health risks. In this study, we developed an innovative method using CoNi@CN-2 nanozymes to activate peroxymonosulfate (PMS) for oxidizing 3,3',5,5'-tetramethylbenzidine (TMB). Our results show that the formation of Ni<sup>2+</sup> through the oxidation of Ni<sup>0</sup> on the CoNi@CN-2 surface significantly enhances the electron-donating capacity of Co<sup>0</sup>. The catalytic reaction of TMB is mediated by redox active species (SO<sub>4</sub><sup>•−</sup>, •O<sub>2</sub><sup>−</sup>, •OH and <sup>1</sup>O<sub>2</sub>). RS drives colorimetry by transferring electrons to the benzene ring and specific nitrogen atoms in ox-TMB, reducing ox-TMB to TMB. Furthermore, the colorimetric assay shows a robust linear correlation between RS concentration and absorbance (Abs), described by Abs = –0.44[RS] + 0.886 (0—200 μmol/L, R<sup>2</sup> = 0.983). Also, we introduce a novel smartphone-integrated autonomous detection software that can analyze RS concentration and grayscale values (GSV), yielding GSV = 0.327[RS] + 63.601 (0—200 μmol/L, <i>R</i><sup>2</sup> = 0.990) with a detection limit of 5.29 μmol/L. Additionally, excess PMS leads to ROS attacking specific sites in ox-TMB, forming secondary oxidation products. This study has enabled rapid and accurate detection of RS, making a significant contribution to environmental safety and protection.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 3","pages":"281-291"},"PeriodicalIF":5.5,"publicationDate":"2024-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143119114","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Modular Access to Chiral 1,3-Substituted Fragments via Nickel-Catalyzed Arylboration Reaction† 通过镍催化芳基硼化反应模块化获得手性 1,3-取代片段†。
IF 5.5 1区 化学
Chinese Journal of Chemistry Pub Date : 2024-10-17 DOI: 10.1002/cjoc.202400742
Yang Bao, Tong Yao, Weiyu Kong, Yangyang Li, Ying Fu, Dong Wu, Guoyin Yin
{"title":"Modular Access to Chiral 1,3-Substituted Fragments via Nickel-Catalyzed Arylboration Reaction†","authors":"Yang Bao,&nbsp;Tong Yao,&nbsp;Weiyu Kong,&nbsp;Yangyang Li,&nbsp;Ying Fu,&nbsp;Dong Wu,&nbsp;Guoyin Yin","doi":"10.1002/cjoc.202400742","DOIUrl":"https://doi.org/10.1002/cjoc.202400742","url":null,"abstract":"<div>\u0000 \u0000 <p>Chiral 1,3-substituted fragments are ubiquitous in pharmaceutical molecules and natural products, prompting the development of numerous methods to access these structures. Nonetheless, devising synthetic routes for complex chiral architectures in practical applications typically demands years of expertise. Herein, we developed a nickel-catalyzed enantioselective migratory arylboration reaction of allylboronic esters using a chiral 1,2-diamine ligand, yielding a range of chiral 1,3-bis(boronates) with high enantioselectivity. The protocol is characterized by its use of commercially available substrates, mild reaction conditions, user-friendly procedures, and a broad substrate compatibility. Moreover, we demonstrate the practicality and application potential of this reaction by synthesizing several key drug intermediates.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 3","pages":"261-267"},"PeriodicalIF":5.5,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143115786","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Recent Advances in Methodologies for Radical-Mechanistic Borylation† 自由基机制硼酸化方法的最新进展
IF 5.5 1区 化学
Chinese Journal of Chemistry Pub Date : 2024-10-17 DOI: 10.1002/cjoc.202400694
Chang Lian, Jianning Zhang, Di Qiu, Fanyang Mo
{"title":"Recent Advances in Methodologies for Radical-Mechanistic Borylation†","authors":"Chang Lian,&nbsp;Jianning Zhang,&nbsp;Di Qiu,&nbsp;Fanyang Mo","doi":"10.1002/cjoc.202400694","DOIUrl":"https://doi.org/10.1002/cjoc.202400694","url":null,"abstract":"<div>\u0000 \u0000 \u0000 <section>\u0000 \u0000 <p>We reviewed works on radical borylation reactions since 2020 from two aspects. <b>1. Borylation from alkyl or aryl radicals</b>: This approach involves the generation of alkyl or aryl radicals from various precursors such as halides and carboxylic acids, followed by their reaction with diboron reagents to form boron esters. <b>2. Borylation from boron-centered radicals</b>: This approach involves generating boron-centered radicals, which then react with substrates to achieve borylation.</p>\u0000 \u0000 <p>\u0000 </p>\u0000 </section>\u0000 \u0000 <section>\u0000 \u0000 <h3> Key Scientists</h3>\u0000 \u0000 <p></p>\u0000 </section>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 1","pages":"104-115"},"PeriodicalIF":5.5,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142759839","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Enabling Access to 3-gem-Difluorovinyl Lactams via Zn-Mediated Sequential Single Electron Reductive Hydrodehalogenation
IF 5.5 1区 化学
Chinese Journal of Chemistry Pub Date : 2024-10-17 DOI: 10.1002/cjoc.202400718
Jia Zheng, Xuran Liu, Jiawen Yin, Shuaikang Li, Juanjuan Zhang, Weigao Hu
{"title":"Enabling Access to 3-gem-Difluorovinyl Lactams via Zn-Mediated Sequential Single Electron Reductive Hydrodehalogenation","authors":"Jia Zheng,&nbsp;Xuran Liu,&nbsp;Jiawen Yin,&nbsp;Shuaikang Li,&nbsp;Juanjuan Zhang,&nbsp;Weigao Hu","doi":"10.1002/cjoc.202400718","DOIUrl":"https://doi.org/10.1002/cjoc.202400718","url":null,"abstract":"<div>\u0000 \u0000 <p>Herein, we describe a direct route for the synthesis of 3-<i>gem</i>-difluorovinyl lactams through Zn-mediated reductive hydrodehalogenation. Importantly, by using inexpensive deuterium oxide (D<sub>2</sub>O), the high value-added vicinal dideuterated <i>gem</i>-difluoroalkenes with excellent deuterium (D) incorporation were prepared. Mechanism studies indicated a successive single electron transfer process: the reaction initially undergoes hydrodechlorination to give the intermediate <i>α-</i>trifluoromethylidene lactams, which are then activated by the <i>in-situ</i> generated zinc cations and reduced to the desired product <i>via</i> hydrodefluorination.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 3","pages":"255-260"},"PeriodicalIF":5.5,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143116381","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Penijanacoranes A—F, Acorane-Type Sesquiterpenes from a Deep Sea-Derived Fungus Penicillium janthinellum SH0301
IF 5.5 1区 化学
Chinese Journal of Chemistry Pub Date : 2024-10-17 DOI: 10.1002/cjoc.202400836
Lu-Jia Yang, Ling Lv, Zhuang Han, Yu-Cheng Gu, Xin Li, Chang-Lun Shao, Zhi-Qing Liu, Chang-Yun Wang
{"title":"Penijanacoranes A—F, Acorane-Type Sesquiterpenes from a Deep Sea-Derived Fungus Penicillium janthinellum SH0301","authors":"Lu-Jia Yang,&nbsp;Ling Lv,&nbsp;Zhuang Han,&nbsp;Yu-Cheng Gu,&nbsp;Xin Li,&nbsp;Chang-Lun Shao,&nbsp;Zhi-Qing Liu,&nbsp;Chang-Yun Wang","doi":"10.1002/cjoc.202400836","DOIUrl":"https://doi.org/10.1002/cjoc.202400836","url":null,"abstract":"<div>\u0000 \u0000 <p>Six new acorane-type sesquiterpenes, named penijanacoranes A—F (<b>1</b>—<b>6</b>), as well as one known eudesmane sesquiterpenoid 1<i>α</i>,6<i>β</i>,11-eudesm-triol (<b>7</b>) have been isolated from a deep-sea-derived fungus <i>Penicillium janthinellum</i> SH0301. Their structures and absolute configurations were established by the comprehensive spectroscopic analysis, TDDFT-ECD calculations, and X-ray diffraction. Penijanacorane A (<b>1</b>) was identified as a rare acorane-type sesquiterpene lactone featuring a novel 6/5/6 tricyclic system, while penijanacoranes E and F (<b>5</b> and <b>6</b>) represented undescribed examples of nor-acorane sesquiterpenes at C-1. Penijanacorane C (<b>3</b>) exhibited significant inhibitory activity against LPS-induced NO production in Raw264.7 macrophages with an IC<sub>50</sub> value of 6.23 μM, which was more potent than that of positive control dexamethasone (IC<sub>50</sub> = 11.49 μM). This study expanded the chemical diversity of acorane-type sesquiterpenoids and revealed that compound <b>3</b> was a potential molecule for anti-inflammatory agents.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 3","pages":"268-274"},"PeriodicalIF":5.5,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143116382","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Ytterbium-Catalyzed Tandem Diels–Alder/Claisen Rearrangement/Decarboxylation of Hetero-Allenes for the Synthesis of Diarylmethanes 镱催化串联双分子- alder /Claisen重排/脱羧杂烯合成二芳基甲烷
IF 5.5 1区 化学
Chinese Journal of Chemistry Pub Date : 2024-10-17 DOI: 10.1002/cjoc.202400874
Bin Chen, Shan Zhong, Huilin Zhan, Zhangyu Han, Jianwei Sun, Hai Huang
{"title":"Ytterbium-Catalyzed Tandem Diels–Alder/Claisen Rearrangement/Decarboxylation of Hetero-Allenes for the Synthesis of Diarylmethanes","authors":"Bin Chen,&nbsp;Shan Zhong,&nbsp;Huilin Zhan,&nbsp;Zhangyu Han,&nbsp;Jianwei Sun,&nbsp;Hai Huang","doi":"10.1002/cjoc.202400874","DOIUrl":"https://doi.org/10.1002/cjoc.202400874","url":null,"abstract":"<div>\u0000 \u0000 <p>A tandem Diels–Alder reaction/Claisen rearrangement/decarboxylation strategy of <i>N</i>-allenamides (or aryloxyallenes) with 3-alkoxycarbonyl-2-pyrones has been developed for the efficient synthesis of diarylmethanes with moderate to good yields. The reaction exhibits good functional group tolerance and can be applied to late-stage modifications of known drug molecules. Mechanistic studies indicate that the ester group at the 3-position of 2-pyrones is essential, and the initial Diels–Alder reaction between the 2-pyrones and the proximal C=C bond of the <i>N</i>-allenamides (or aryloxyallenes) is crucial for the success of the reaction.</p>\u0000 <p></p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 2","pages":"199-204"},"PeriodicalIF":5.5,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142868552","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Catalytic Asymmetric Conjugate Addition and Allylic Substitution of Cyclobutenones with Arylzinc Halides 芳基卤化锌催化环丁烯酮的不对称共轭加成和烯丙基取代
IF 5.5 1区 化学
Chinese Journal of Chemistry Pub Date : 2024-10-17 DOI: 10.1002/cjoc.202400882
Renming Pan, Ping Lu
{"title":"Catalytic Asymmetric Conjugate Addition and Allylic Substitution of Cyclobutenones with Arylzinc Halides","authors":"Renming Pan,&nbsp;Ping Lu","doi":"10.1002/cjoc.202400882","DOIUrl":"https://doi.org/10.1002/cjoc.202400882","url":null,"abstract":"<div>\u0000 \u0000 <p>Conjugate addition and allylic substitution are two essential chemical transformations, and they could be competitive for substrates with multiple reactive sites. Herein, we report the diversified enantioselective synthesis of cyclobutenes via the functionalization of cyclobutenones. The conjugate addition of cyclobutenones with arylzinc halides provided enantioenriched cyclobutenes with all-carbon quaternary centers. On the other hand, when cyclobutenones with <i>gem</i>-dichloro groups were employed, a chemo- and enantioselective allylic substitution occurred. Further synthetic utility was demonstrated for synthesizing versatile cyclobutane derivatives, together with ring-opening and expansion products.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 2","pages":"184-190"},"PeriodicalIF":5.5,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142868554","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Tumor Cell-Specific Metabolic Labelling of Surface Sialoglycans and Post-Click with Multivalent Rhamnose Enable Precise Immune Killing by Endogenous Antibody 表面唾液聚糖的肿瘤细胞特异性代谢标记和多价鼠李糖的Post-Click实现内源性抗体的精确免疫杀伤
IF 5.5 1区 化学
Chinese Journal of Chemistry Pub Date : 2024-10-16 DOI: 10.1002/cjoc.202400855
Haofei Hong, Yanchun Li, Dan Li, Han Lin, Jie Zhao, Zheng Wang, Zhimeng Wu
{"title":"Tumor Cell-Specific Metabolic Labelling of Surface Sialoglycans and Post-Click with Multivalent Rhamnose Enable Precise Immune Killing by Endogenous Antibody","authors":"Haofei Hong,&nbsp;Yanchun Li,&nbsp;Dan Li,&nbsp;Han Lin,&nbsp;Jie Zhao,&nbsp;Zheng Wang,&nbsp;Zhimeng Wu","doi":"10.1002/cjoc.202400855","DOIUrl":"https://doi.org/10.1002/cjoc.202400855","url":null,"abstract":"<div>\u0000 \u0000 <p>\u0000 </p><blockquote><p>We report the design and development of a β-glucuronidase (β-Glu)-responsive ManNAz derivative, Glu-AAM, for tumor-selective metabolic glycoengineering. Glu-AAM enables specific labeling of tumor cell surface sialoglycans in the presence of overexpressed β-Glu in cancer cells, including breast, leukemia, and colorectal cancer cells. We demonstrate the high selectivity and efficiency of Glu-AAM-mediated metabolic glycoengineering across multiple cancer cell lines. Furthermore, we synthesized multivalent antibody-recruiting molecules (DBCO-Rha) that can be covalently attached to the azido-modified tumor cell surface, leading to potent antibody-dependent cellular phagocytosis and complement-dependent cytotoxicity. The octameric DBCO-Rha8 construct exhibited the most effective immune response. This integrated strategy of β-Glu-responsive metabolic glycoengineering and antibody-recruiting immunotherapy provides a promising platform for targeted cancer therapies and expands the toolbox of metabolic glycoengineering for cancer immunotherapy.</p><p>\u0000 </p>\u0000 <div></div>\u0000 </blockquote>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 1","pages":"46-52"},"PeriodicalIF":5.5,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142762785","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
An Intelligent Triple Assisted Gold Cluster-Based Nanosystem for Enhanced Tumor Photodynamic Therapy 用于增强肿瘤光动力治疗的智能三辅助金簇纳米系统
IF 5.5 1区 化学
Chinese Journal of Chemistry Pub Date : 2024-10-16 DOI: 10.1002/cjoc.202400837
Fangli Gao, Yanru Liu, Liang Zhu, Jie Zhang, Yi Chang, Weihua Gao, Guanglei Ma, Xiaoming Ma, Yuming Guo
{"title":"An Intelligent Triple Assisted Gold Cluster-Based Nanosystem for Enhanced Tumor Photodynamic Therapy","authors":"Fangli Gao,&nbsp;Yanru Liu,&nbsp;Liang Zhu,&nbsp;Jie Zhang,&nbsp;Yi Chang,&nbsp;Weihua Gao,&nbsp;Guanglei Ma,&nbsp;Xiaoming Ma,&nbsp;Yuming Guo","doi":"10.1002/cjoc.202400837","DOIUrl":"https://doi.org/10.1002/cjoc.202400837","url":null,"abstract":"<div>\u0000 \u0000 <p>Photodynamic therapy (PDT) has been attracted a surge of research interest. However, there are several obstacles to limit the efficacy of PDT, such as hypoxic tumor microenvironment (TME), overexpressed glutathione (GSH), inefficient reactive oxygen species (ROS) generation, and so on. Herein, a smart responsive nanosystem was constructed, which was composed of Au<sub>25</sub> modified with triphenylphosphine (Au<sub>25</sub>-TPP), catalase (CAT) and GSH-responsive diselenide-bridged mesoporous silica nanoparticles (Se-MSN). When the nanosystem arrived at tumor site, Se-MSN was degraded by the intracellular overexpressed GSH to release Au<sub>25</sub>-TPP and CAT. The Au<sub>25</sub>-TPP was targeted to mitochondria and generated ROS under the 808 nm NIR laser irradiation to kill tumor cells. Simultaneously, CAT could catalyze hydrogen peroxide to provide oxygen for relieving the hypoxia of TME. Besides, GSH was consumed by the diselenide bond to diminish the ROS loss. The above tactics (mitochondria targeting, hypoxia relieving and GSH consuming) jointly enhanced the PDT efficacy. The nanosystem showed distinct <i>in vitro</i> anticancer effect significantly stronger than other groups containing one or two assistance. Moreover, the <i>in vivo</i> results suggested that the tumors could be restrained obviously. The current study provides a new inspiration for constructing novel inorganic nanomedicines with multiple enhancement effect of PDT efficacy.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 2","pages":"175-183"},"PeriodicalIF":5.5,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142868524","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photolabile ortho-Nitro-Benzyl Carbonate as a Permanent Hydroxyl Protecting Group for the Synthesis of Digalactosyl Diacylglycerol 光不稳定的邻硝基碳酸苄作为永久羟基保护基用于合成双半乳糖二酰基甘油
IF 5.5 1区 化学
Chinese Journal of Chemistry Pub Date : 2024-10-16 DOI: 10.1002/cjoc.202400866
Jibin Zheng, Hongyu Chen, Jintao Shang, Lvfeng Zhang, Youling Liang, Dongsheng Chang, You Yang
{"title":"Photolabile ortho-Nitro-Benzyl Carbonate as a Permanent Hydroxyl Protecting Group for the Synthesis of Digalactosyl Diacylglycerol","authors":"Jibin Zheng,&nbsp;Hongyu Chen,&nbsp;Jintao Shang,&nbsp;Lvfeng Zhang,&nbsp;Youling Liang,&nbsp;Dongsheng Chang,&nbsp;You Yang","doi":"10.1002/cjoc.202400866","DOIUrl":"https://doi.org/10.1002/cjoc.202400866","url":null,"abstract":"<div>\u0000 \u0000 <p>Traditional protecting groups are often removed under harsh conditions with potentially hazardous reagents, thereby impeding the convenient synthesis of oligosaccharides and glycosides. Herein, we present to utilize the photolabile <i>ortho</i>-nitro-benzyl carbonate (<i>o</i>NBC) as a permanent hydroxyl protecting group for stereocontrolled synthesis of glycosides. The Ph<sub>3</sub>PO-modulated glycosylation with strongly disarmed per-<i>O</i>-<i>o</i>NBC-protected glycosyl ynenoates preferred to afford glycosides with excellent α-selectivities via the β-phosphonium transition state. Based on the <i>o</i>NBC-mediated galactosylation, synthesis of the glycolipid digalactosyl diacylglycerol (DGDG) containing six double bonds and two esters was achieved in a straightforward manner.</p>\u0000 <p>\u0000 </p>\u0000 </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 2","pages":"169-174"},"PeriodicalIF":5.5,"publicationDate":"2024-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142868523","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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