首页 > 最新文献

JACS Au最新文献

英文 中文
Defluorinative Multicomponent Cascade Reaction of Trifluoromethylarenes via Photoexcited Palladium Catalysis 通过光激发钯催化三氟甲基烯的去氟多组分级联反应
IF 8.5 Q1 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-11-06 DOI: 10.1021/jacsau.4c0089910.1021/jacsau.4c00899
Zhibin Li, Lei Bao, Kaihang Wei, Beibei Zhan, Ping Lu and Xiaheng Zhang*, 

The incorporation of aromatic difluoromethyl motifs has proven to be a fruitful strategy for enhancing the therapeutic profiles of modern pharmaceutical candidates. While the defluorofunctionalization of trifluoromethylarenes offers a promising pathway toward diverse aromatic difluoromethyl compounds, current methods are predominantly limited to two-component reactions. Multicomponent cascade reactions (MCRs) involving a transient aromatic difluoromethyl radical are still uncommon and highly sought after, owing to their capacity to rapidly generate challenging molecular structures. In this study, we present a photocatalytic manifold that combines commercially available trifluoromethylarenes, feedstock dienes, and various nucleophiles to achieve a modular defluorinative MCR. This method features mild reaction conditions and a broad substrate scope with excellent functional group compatibility. Furthermore, this protocol enables a previously unreported process of defluorinative editing for the resulting MCR aromatic difluoromethyl adducts. Preliminary mechanistic studies support the proposed photoexcited palladium catalytic cycle.

事实证明,加入芳香族二氟甲基基团是提高现代候选药物治疗效果的有效策略。虽然三氟甲基烯烃的脱氟官能化为获得多种芳香族二氟甲基化合物提供了一条前景广阔的途径,但目前的方法主要局限于双组分反应。涉及瞬时芳香二氟甲基自由基的多组分级联反应(MCR)仍不常见,但由于其能够快速生成具有挑战性的分子结构,因此备受追捧。在本研究中,我们介绍了一种光催化歧管,它将市售的三氟甲基烯烃、原料二烯和各种亲核剂结合在一起,实现了模块化脱氟 MCR。这种方法的特点是反应条件温和,底物范围广,官能团兼容性极佳。此外,该方法还能对 MCR 生成的芳香族二氟甲基加合物进行之前未报道过的脱氟编辑。初步的机理研究支持所提出的光激发钯催化循环。
{"title":"Defluorinative Multicomponent Cascade Reaction of Trifluoromethylarenes via Photoexcited Palladium Catalysis","authors":"Zhibin Li,&nbsp;Lei Bao,&nbsp;Kaihang Wei,&nbsp;Beibei Zhan,&nbsp;Ping Lu and Xiaheng Zhang*,&nbsp;","doi":"10.1021/jacsau.4c0089910.1021/jacsau.4c00899","DOIUrl":"https://doi.org/10.1021/jacsau.4c00899https://doi.org/10.1021/jacsau.4c00899","url":null,"abstract":"<p >The incorporation of aromatic difluoromethyl motifs has proven to be a fruitful strategy for enhancing the therapeutic profiles of modern pharmaceutical candidates. While the defluorofunctionalization of trifluoromethylarenes offers a promising pathway toward diverse aromatic difluoromethyl compounds, current methods are predominantly limited to two-component reactions. Multicomponent cascade reactions (MCRs) involving a transient aromatic difluoromethyl radical are still uncommon and highly sought after, owing to their capacity to rapidly generate challenging molecular structures. In this study, we present a photocatalytic manifold that combines commercially available trifluoromethylarenes, feedstock dienes, and various nucleophiles to achieve a modular defluorinative MCR. This method features mild reaction conditions and a broad substrate scope with excellent functional group compatibility. Furthermore, this protocol enables a previously unreported process of defluorinative editing for the resulting MCR aromatic difluoromethyl adducts. Preliminary mechanistic studies support the proposed photoexcited palladium catalytic cycle.</p>","PeriodicalId":94060,"journal":{"name":"JACS Au","volume":"4 11","pages":"4223–4233 4223–4233"},"PeriodicalIF":8.5,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/jacsau.4c00899","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142694424","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Iridium-Catalyzed Enantioselective Vinylogous and Bisvinylogous Allenylic Substitution 铱催化的对映选择性乙烯基和双乙烯基烯丙基取代反应
IF 8.5 Q1 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-11-05 DOI: 10.1021/jacsau.4c0064010.1021/jacsau.4c00640
Sankash Mitra,  and , Santanu Mukherjee*, 

Compared to the widely explored enol silanes, the applicability of their extended variants especially as bisvinylogous nucleophiles in enantioselective catalysis has been sparse. Herein, we describe the first enantioselective vinylogous and bisvinylogous allenylic substitution using silyl dienol and trienol ethers, respectively, as a nucleophile. With racemic allenylic alcohols as the electrophile, these enantioconvergent reactions are cooperatively catalyzed by an Ir(I)/(phosphoramidite,olefin) complex and Lewis acidic La(OTf)3 and display remarkable regio- and diastereoselectivity in most cases. The ability of such extended silyl enol ethers in distant functionalization and creation of remote stereocenters is evident from the resulting γ- and ε-allenylic unsaturated ketones, bearing δ- and ζ-stereocenters, respectively, which are obtained in moderate to high yields with good to excellent enantioselectivity. The synthetic utility of these unsaturated carbonyls bearing an allene moiety is demonstrated with several transformations, including controlled reductions and stereoselective olefinations, which lead to products with desired degrees of unsaturation.

与已被广泛开发的烯醇硅烷相比,其扩展变体(尤其是作为双乙烯基亲核物)在对映选择性催化中的应用还很稀少。在此,我们介绍了分别以硅基二元醇和三元醇醚为亲核体的首次对映选择性乙烯基和双乙烯基异烯基取代反应。这些对映转化反应以外消旋别烯醇为亲电体,由 Ir(I)/(磷酰胺,烯烃)复合物和路易斯酸性 La(OTf)3 协同催化,在大多数情况下具有显著的区域和非对映选择性。从得到的分别带有 δ- 和 ζ-立体中心的 γ- 和 ε- 烯基不饱和酮中可以明显看出这种扩展硅基烯醚在远官能化和创建远立体中心方面的能力。通过几种转化方法,包括受控还原和立体选择性烯化,这些带有一个烯基的不饱和羰基的合成效用得到了证明,从而得到了具有所需不饱和度的产物。
{"title":"Iridium-Catalyzed Enantioselective Vinylogous and Bisvinylogous Allenylic Substitution","authors":"Sankash Mitra,&nbsp; and ,&nbsp;Santanu Mukherjee*,&nbsp;","doi":"10.1021/jacsau.4c0064010.1021/jacsau.4c00640","DOIUrl":"https://doi.org/10.1021/jacsau.4c00640https://doi.org/10.1021/jacsau.4c00640","url":null,"abstract":"<p >Compared to the widely explored enol silanes, the applicability of their extended variants especially as bisvinylogous nucleophiles in enantioselective catalysis has been sparse. Herein, we describe the first enantioselective vinylogous and bisvinylogous allenylic substitution using silyl dienol and trienol ethers, respectively, as a nucleophile. With racemic allenylic alcohols as the electrophile, these enantioconvergent reactions are cooperatively catalyzed by an Ir(I)/(phosphoramidite,olefin) complex and Lewis acidic La(OTf)<sub>3</sub> and display remarkable regio- and diastereoselectivity in most cases. The ability of such extended silyl enol ethers in distant functionalization and creation of remote stereocenters is evident from the resulting γ- and ε-allenylic unsaturated ketones, bearing δ- and ζ-stereocenters, respectively, which are obtained in moderate to high yields with good to excellent enantioselectivity. The synthetic utility of these unsaturated carbonyls bearing an allene moiety is demonstrated with several transformations, including controlled reductions and stereoselective olefinations, which lead to products with desired degrees of unsaturation.</p>","PeriodicalId":94060,"journal":{"name":"JACS Au","volume":"4 11","pages":"4285–4294 4285–4294"},"PeriodicalIF":8.5,"publicationDate":"2024-11-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/jacsau.4c00640","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142694604","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Controllable Enzymatic Synthesis of Natural Asymmetric Human Milk Oligosaccharides 天然不对称人乳低聚糖的可控酶法合成
IF 8.5 Q1 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-11-02 DOI: 10.1021/jacsau.4c0083010.1021/jacsau.4c00830
Hsien-Wei Tseng, Hsin-Kai Tseng, Kai-Eng Ooi, Cheng-En You, Hung-Kai Wang, Wen-Hua Kuo, Chi-Kung Ni, Yoshiyuki Manabe and Chun-Cheng Lin*, 

Among human milk oligosaccharides (HMOs), linear HMOs are synthesized through mature but varied routes. Although branched HMOs can be synthesized by chemical, enzymatic, or chemoenzymatic methods, these methods cannot be easily applied to the synthesis of asymmetric multiantennary oligosaccharides. Herein, we developed a controllable method to synthesize asymmetric biantennary HMOs. In our synthetic route, GlcNAcβ1,3(GlcN3β1,6)Glaβ1,4Glc was first chemically synthesized as the core tetrasaccharide, which contains β1,6GlcN3 as the “stop” sugar in transferase-catalyzed glycosylation. The desired sugars at the GlcNAcβ1–3Gal arm can be assembled using galactosyltransferase, N-acetylglucosaminyltransferase, and fucosyltransferase. Then, the Staudinger reduction and acetylation were used to transform GlcN3 to GlcNAc and assemble sugars by initiating the “go” process. By manipulating transferase-catalyzed glycosylations, 22 natural asymmetric biantennary oligosaccharides were synthesized.

在母乳低聚糖(HMOs)中,线性 HMOs 的合成路线成熟而多样。虽然支链 HMOs 可以通过化学、酶法或化学酶法合成,但这些方法并不容易应用于不对称多双链寡糖的合成。在此,我们开发了一种可控的方法来合成不对称双端 HMO。在我们的合成路线中,GlcNAcβ1,3(GlcN3β1,6)Glaβ1,4Glc首先被化学合成为核心四糖,其中含有β1,6GlcN3作为转移酶催化糖基化过程中的 "终止 "糖。利用半乳糖基转移酶、N-乙酰葡糖胺基转移酶和岩藻糖基转移酶可以在 GlcNAcβ1-3Gal 臂上合成所需的糖。然后,利用施陶丁格还原和乙酰化将 GlcN3 转化为 GlcNAc,并通过启动 "去 "过程来组装糖。通过操纵转移酶催化的糖基化过程,合成了 22 种天然不对称双年轮寡糖。
{"title":"Controllable Enzymatic Synthesis of Natural Asymmetric Human Milk Oligosaccharides","authors":"Hsien-Wei Tseng,&nbsp;Hsin-Kai Tseng,&nbsp;Kai-Eng Ooi,&nbsp;Cheng-En You,&nbsp;Hung-Kai Wang,&nbsp;Wen-Hua Kuo,&nbsp;Chi-Kung Ni,&nbsp;Yoshiyuki Manabe and Chun-Cheng Lin*,&nbsp;","doi":"10.1021/jacsau.4c0083010.1021/jacsau.4c00830","DOIUrl":"https://doi.org/10.1021/jacsau.4c00830https://doi.org/10.1021/jacsau.4c00830","url":null,"abstract":"<p >Among human milk oligosaccharides (HMOs), linear HMOs are synthesized through mature but varied routes. Although branched HMOs can be synthesized by chemical, enzymatic, or chemoenzymatic methods, these methods cannot be easily applied to the synthesis of asymmetric multiantennary oligosaccharides. Herein, we developed a controllable method to synthesize asymmetric biantennary HMOs. In our synthetic route, GlcNAcβ1,3(GlcN3β1,6)Glaβ1,4Glc was first chemically synthesized as the core tetrasaccharide, which contains β1,6GlcN3 as the “stop” sugar in transferase-catalyzed glycosylation. The desired sugars at the GlcNAcβ1–3Gal arm can be assembled using galactosyltransferase, <i>N</i>-acetylglucosaminyltransferase, and fucosyltransferase. Then, the Staudinger reduction and acetylation were used to transform GlcN3 to GlcNAc and assemble sugars by initiating the “go” process. By manipulating transferase-catalyzed glycosylations, 22 natural asymmetric biantennary oligosaccharides were synthesized.</p>","PeriodicalId":94060,"journal":{"name":"JACS Au","volume":"4 11","pages":"4496–4506 4496–4506"},"PeriodicalIF":8.5,"publicationDate":"2024-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/jacsau.4c00830","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142694555","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Precise Regulations at the Subcellular Level through Intracellular Polymerization, Assembly, and Transformation 通过胞内聚合、组装和转化实现亚细胞水平的精确调节
IF 8.5 Q1 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-11-01 DOI: 10.1021/jacsau.4c0084910.1021/jacsau.4c00849
Le He, Fanying Meng, Ran Chen, Jinlong Qin, Min Sun*, Zhen Fan* and Jianzhong Du*, 

A living cell is an intricate machine that creates subregions to operate cell functions effectively. Subcellular dysfunction has been identified as a potential druggable target for successful drug design and therapy. The treatments based on intracellular polymerization, self-assembly, or transformation offer various advantages, including enhanced blood circulation of monomers, long-term drug delivery pharmacokinetics, low drug resistance, and the ability to target deep tissues and organelles. In this review, we discuss the latest developments of intracellular synthesis applied to precisely control cellular functions. First, we discuss the design and applications of endogenous and exogenous stimuli-triggered intracellular polymerization, self-assembly, and dynamic morphology transformation of biomolecules at the subcellular level. Second, we highlight the benefits of these strategies applied in cancer diagnosis and treatment and modulating cellular states or cell metabolism of living systems. Finally, we conclude the recent progress in this field, discuss future perspectives, analyze the challenges of the intracellular functional reactions for regulation, and find future opportunities.

活细胞是一台复杂的机器,它创造出亚区域,使细胞功能有效运行。亚细胞功能障碍已被确定为成功设计和治疗药物的潜在药物靶点。基于细胞内聚合、自组装或转化的治疗方法具有各种优势,包括增强单体的血液循环、长期给药的药代动力学、低耐药性以及靶向深层组织和细胞器的能力。在这篇综述中,我们将讨论应用于精确控制细胞功能的细胞内合成的最新进展。首先,我们讨论了内源性和外源性刺激触发的细胞内聚合、自组装以及亚细胞水平生物大分子动态形态转化的设计和应用。其次,我们强调了这些策略应用于癌症诊断和治疗以及调节生命系统的细胞状态或细胞新陈代谢的益处。最后,我们总结了这一领域的最新进展,讨论了未来前景,分析了细胞内功能反应调控所面临的挑战,并寻找未来的机遇。
{"title":"Precise Regulations at the Subcellular Level through Intracellular Polymerization, Assembly, and Transformation","authors":"Le He,&nbsp;Fanying Meng,&nbsp;Ran Chen,&nbsp;Jinlong Qin,&nbsp;Min Sun*,&nbsp;Zhen Fan* and Jianzhong Du*,&nbsp;","doi":"10.1021/jacsau.4c0084910.1021/jacsau.4c00849","DOIUrl":"https://doi.org/10.1021/jacsau.4c00849https://doi.org/10.1021/jacsau.4c00849","url":null,"abstract":"<p >A living cell is an intricate machine that creates subregions to operate cell functions effectively. Subcellular dysfunction has been identified as a potential druggable target for successful drug design and therapy. The treatments based on intracellular polymerization, self-assembly, or transformation offer various advantages, including enhanced blood circulation of monomers, long-term drug delivery pharmacokinetics, low drug resistance, and the ability to target deep tissues and organelles. In this review, we discuss the latest developments of intracellular synthesis applied to precisely control cellular functions. First, we discuss the design and applications of endogenous and exogenous stimuli-triggered intracellular polymerization, self-assembly, and dynamic morphology transformation of biomolecules at the subcellular level. Second, we highlight the benefits of these strategies applied in cancer diagnosis and treatment and modulating cellular states or cell metabolism of living systems. Finally, we conclude the recent progress in this field, discuss future perspectives, analyze the challenges of the intracellular functional reactions for regulation, and find future opportunities.</p>","PeriodicalId":94060,"journal":{"name":"JACS Au","volume":"4 11","pages":"4162–4186 4162–4186"},"PeriodicalIF":8.5,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/jacsau.4c00849","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142694487","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Water-Microdroplet-Driven Interface-Charged Chemistries 水微滴驱动的界面充注化学工艺
IF 8.5 Q1 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-10-31 DOI: 10.1021/jacsau.4c0080410.1021/jacsau.4c00804
Xiuquan Jia, Jianhan Wu and Feng Wang*, 

Water has made Earth a habitable planet by electrifying the troposphere. For example, the lightning caused by the electrification and discharge of cloudwater microdroplets is closely related to atmospheric chemistry. Recent work has revealed that a high electric field exists at the interface of water microdroplets, which is ∼3 orders of magnitude higher than the electric field that accounts for lightning. A surge of exotic redox reactions that were recently found over water microdroplets can be contributed by such an interfacial electric field. However, the role of net charge in microdroplet redox chemistry should not be ignored. In this Perspective, we show how redox reactions can be driven by electron transfer pathways in the electrification and discharge process of water microdroplets. Understanding and harnessing the origin and evolution of charged microdroplets are likely to lead to a paradigm shift of electrochemistry, which may play an overlooked role in geological and environmental chemistry.

水使对流层通电,从而使地球成为宜居星球。例如,云水微滴的电化和放电引起的闪电与大气化学密切相关。最近的研究发现,在水微滴的界面上存在一个高电场,这个电场比闪电的电场高出 3 个数量级。最近在水微滴上发现的大量奇异氧化还原反应可能就是由这种界面电场引起的。然而,净电荷在微滴氧化还原化学中的作用也不容忽视。在本《视角》中,我们将展示在水微滴的通电和放电过程中,氧化还原反应是如何由电子传递途径驱动的。了解和利用带电微滴的起源和演化很可能会导致电化学范式的转变,这可能会在地质和环境化学中发挥被忽视的作用。
{"title":"Water-Microdroplet-Driven Interface-Charged Chemistries","authors":"Xiuquan Jia,&nbsp;Jianhan Wu and Feng Wang*,&nbsp;","doi":"10.1021/jacsau.4c0080410.1021/jacsau.4c00804","DOIUrl":"https://doi.org/10.1021/jacsau.4c00804https://doi.org/10.1021/jacsau.4c00804","url":null,"abstract":"<p >Water has made Earth a habitable planet by electrifying the troposphere. For example, the lightning caused by the electrification and discharge of cloudwater microdroplets is closely related to atmospheric chemistry. Recent work has revealed that a high electric field exists at the interface of water microdroplets, which is ∼3 orders of magnitude higher than the electric field that accounts for lightning. A surge of exotic redox reactions that were recently found over water microdroplets can be contributed by such an interfacial electric field. However, the role of net charge in microdroplet redox chemistry should not be ignored. In this Perspective, we show how redox reactions can be driven by electron transfer pathways in the electrification and discharge process of water microdroplets. Understanding and harnessing the origin and evolution of charged microdroplets are likely to lead to a paradigm shift of electrochemistry, which may play an overlooked role in geological and environmental chemistry.</p>","PeriodicalId":94060,"journal":{"name":"JACS Au","volume":"4 11","pages":"4141–4147 4141–4147"},"PeriodicalIF":8.5,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/jacsau.4c00804","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142694613","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Slow-Binding and Covalent HDAC Inhibition: A New Paradigm? 慢结合和共价 HDAC 抑制:新范例?
IF 8.5 Q1 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-10-31 DOI: 10.1021/jacsau.4c0082810.1021/jacsau.4c00828
Yasir S. Raouf*,  and , Carlos Moreno-Yruela*, 

The dysregulated post-translational modification of proteins is an established hallmark of human disease. Through Zn2+-dependent hydrolysis of acyl-lysine modifications, histone deacetylases (HDACs) are key regulators of disease-implicated signaling pathways and tractable drug targets in the clinic. Early targeting of this family of 11 enzymes (HDAC1–11) afforded a first generation of broadly acting inhibitors with medicinal applications in oncology, specifically in cutaneous and peripheral T-cell lymphomas and in multiple myeloma. However, first-generation HDAC inhibitors are often associated with weak-to-modest patient benefits, dose-limited efficacies, pharmacokinetic liabilities, and recurring clinical toxicities. Alternative inhibitor design to target single enzymes and avoid toxic Zn2+-binding moieties have not overcome these limitations. Instead, recent literature has seen a shift toward noncanonical mechanistic approaches focused on slow-binding and covalent inhibition. Such compounds hold the potential of improving the pharmacokinetic and pharmacodynamic profiles of HDAC inhibitors through the extension of the drug–target residence time. This perspective aims to capture this emerging paradigm and discuss its potential to improve the preclinical/clinical outlook of HDAC inhibitors in the coming years.

蛋白质翻译后修饰失调是人类疾病的既定特征。通过 Zn2+ 依赖性水解酰基赖氨酸修饰,组蛋白去乙酰化酶(HDACs)是影响疾病的信号通路的关键调节因子,也是临床上可行的药物靶点。早期以这个由 11 种酶组成的家族(HDAC1-11)为靶点,开发出了第一代作用广泛的抑制剂,并将其应用于肿瘤学领域,特别是皮肤淋巴瘤、外周 T 细胞淋巴瘤和多发性骨髓瘤。然而,第一代 HDAC 抑制剂对患者的益处往往微乎其微、疗效受剂量限制、药代动力学缺陷以及反复出现的临床毒性。针对单一酶和避免有毒 Zn2+ 结合分子的替代抑制剂设计并没有克服这些局限性。相反,最近的文献显示,人们开始转向非经典的机理方法,侧重于缓慢结合和共价抑制。通过延长药物在靶点的停留时间,此类化合物有望改善 HDAC 抑制剂的药代动力学和药效学特征。本视角旨在捕捉这一新兴范例,并讨论其在未来几年改善 HDAC 抑制剂临床前/临床前景的潜力。
{"title":"Slow-Binding and Covalent HDAC Inhibition: A New Paradigm?","authors":"Yasir S. Raouf*,&nbsp; and ,&nbsp;Carlos Moreno-Yruela*,&nbsp;","doi":"10.1021/jacsau.4c0082810.1021/jacsau.4c00828","DOIUrl":"https://doi.org/10.1021/jacsau.4c00828https://doi.org/10.1021/jacsau.4c00828","url":null,"abstract":"<p >The dysregulated post-translational modification of proteins is an established hallmark of human disease. Through Zn<sup>2+</sup>-dependent hydrolysis of acyl-lysine modifications, histone deacetylases (HDACs) are key regulators of disease-implicated signaling pathways and tractable drug targets in the clinic. Early targeting of this family of 11 enzymes (HDAC1–11) afforded a first generation of broadly acting inhibitors with medicinal applications in oncology, specifically in cutaneous and peripheral T-cell lymphomas and in multiple myeloma. However, first-generation HDAC inhibitors are often associated with weak-to-modest patient benefits, dose-limited efficacies, pharmacokinetic liabilities, and recurring clinical toxicities. Alternative inhibitor design to target single enzymes and avoid toxic Zn<sup>2+</sup>-binding moieties have not overcome these limitations. Instead, recent literature has seen a shift toward noncanonical mechanistic approaches focused on slow-binding and covalent inhibition. Such compounds hold the potential of improving the pharmacokinetic and pharmacodynamic profiles of HDAC inhibitors through the extension of the drug–target residence time. This perspective aims to capture this emerging paradigm and discuss its potential to improve the preclinical/clinical outlook of HDAC inhibitors in the coming years.</p>","PeriodicalId":94060,"journal":{"name":"JACS Au","volume":"4 11","pages":"4148–4161 4148–4161"},"PeriodicalIF":8.5,"publicationDate":"2024-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/jacsau.4c00828","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142694614","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Kinetic and Mechanistic Studies of Native Chemical Ligation with Phenyl α-Selenoester Peptides 与苯基 α-硒酯肽原生化学连接的动力学和机理研究
IF 8.5 Q1 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-10-30 DOI: 10.1021/jacsau.4c0070510.1021/jacsau.4c00705
Iván Sánchez-Campillo,  and , Juan B. Blanco-Canosa*, 

Native chemical ligation (NCL) ligates two unprotected peptides in an aqueous buffer. One of the fragments features a C-terminal α-thioester functional group, and the second bears an N-terminal cysteine. The reaction mechanism depicts two steps: an intermolecular thiol–thioester exchange resulting in a transient thioester, followed by an intramolecular S-to-N acyl shift to yield the final native peptide bond. Although this mechanism is well established, the direct observation of the transient thioester has been elusive because the fast intramolecular rearrangement prevents its accumulation. Here, the use of α-selenoester peptides allows a faster first reaction and an early buildup of the intermediate, enabling its quantification and the kinetic monitoring of the first and second steps. The results show a correlation between the steric hindrance in the α-thioester residue and the rearrangement rate. In bulky residues, the S-to-N acyl shift has a significant contribution to the overall reaction rate. This is particularly notable for valine and likely for other similar β-branched amino acids.

原生化学连接(NCL)是在水性缓冲液中连接两个未受保护的肽段。其中一个片段具有 C 端 α 硫代酯官能团,第二个片段具有 N 端半胱氨酸。反应机理分为两个步骤:分子间硫醇-硫代酯交换产生瞬时硫代酯,随后分子内 S-N酰基转移产生最终的原生肽键。虽然这一机制已被证实,但瞬时硫代酯的直接观察却一直难以实现,因为分子内的快速重排阻碍了其积累。在这里,使用 α-硫代酯肽可以更快地进行第一反应,及早积累中间体,从而对其进行定量,并对第一和第二步进行动力学监测。结果表明,α-硫酯残基中的立体阻碍与重排速率之间存在相关性。在笨重的残基中,S-N酰基转移对整个反应速率有显著的影响。这一点在缬氨酸中尤为明显,其他类似的 β-支链氨基酸也可能如此。
{"title":"Kinetic and Mechanistic Studies of Native Chemical Ligation with Phenyl α-Selenoester Peptides","authors":"Iván Sánchez-Campillo,&nbsp; and ,&nbsp;Juan B. Blanco-Canosa*,&nbsp;","doi":"10.1021/jacsau.4c0070510.1021/jacsau.4c00705","DOIUrl":"https://doi.org/10.1021/jacsau.4c00705https://doi.org/10.1021/jacsau.4c00705","url":null,"abstract":"<p >Native chemical ligation (NCL) ligates two unprotected peptides in an aqueous buffer. One of the fragments features a C-terminal α-thioester functional group, and the second bears an N-terminal cysteine. The reaction mechanism depicts two steps: an intermolecular thiol–thioester exchange resulting in a transient thioester, followed by an intramolecular <i>S-to-N</i> acyl shift to yield the final native peptide bond. Although this mechanism is well established, the direct observation of the transient thioester has been elusive because the fast intramolecular rearrangement prevents its accumulation. Here, the use of α-selenoester peptides allows a faster first reaction and an early buildup of the intermediate, enabling its quantification and the kinetic monitoring of the first and second steps. The results show a correlation between the steric hindrance in the α-thioester residue and the rearrangement rate. In bulky residues, the <i>S-to-N</i> acyl shift has a significant contribution to the overall reaction rate. This is particularly notable for valine and likely for other similar β-branched amino acids.</p>","PeriodicalId":94060,"journal":{"name":"JACS Au","volume":"4 11","pages":"4374–4382 4374–4382"},"PeriodicalIF":8.5,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/jacsau.4c00705","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142694517","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
eCyanation Using 5-Aminotetrazole As a Safer Electrophilic and Nucleophilic Cyanide Source 使用 5-氨基四氮唑作为更安全的亲电和亲核氰化源的电子氰化法
IF 8.5 Q1 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-10-30 DOI: 10.1021/jacsau.4c0076810.1021/jacsau.4c00768
Valerio Morlacci, Marco Milia, Jérémy Saiter, Irene Preet Bhela, Matthew C. Leech and Kevin Lam*, 

An electrochemical method for carrying out safer cyanation reactions is reported. The use of 5-aminotetrazole as a cyanide source enabled the successful electrogeneration of both electrophilic and nucleophilic cyanide sources. To demonstrate the versatility of the method, a variety of cyanation reactions were carried out, including the synthesis of cyanamides, N-heterocycles, and aromatic nitriles, as well as the nucleophilic addition of cyanides to a variety of electrophiles without the need to handle highly toxic cyanide salts. Finally, as a proof of concept for scalability, the cyanation methodology was rapidly transferred to a flow electrosynthesis setup, which demonstrated its potential for large-scale applications.

报告了一种进行更安全氰化反应的电化学方法。使用 5-aminotetrazole 作为氰化源,成功实现了亲电和亲核氰化源的电生成。为了证明该方法的多功能性,研究人员进行了多种氰化反应,包括氰化物、N-杂环和芳香腈的合成,以及氰化物与多种亲电体的亲核加成反应,而无需处理剧毒氰盐。最后,作为可扩展性概念的验证,氰化方法被迅速转移到了流动电合成装置中,从而证明了其大规模应用的潜力。
{"title":"eCyanation Using 5-Aminotetrazole As a Safer Electrophilic and Nucleophilic Cyanide Source","authors":"Valerio Morlacci,&nbsp;Marco Milia,&nbsp;Jérémy Saiter,&nbsp;Irene Preet Bhela,&nbsp;Matthew C. Leech and Kevin Lam*,&nbsp;","doi":"10.1021/jacsau.4c0076810.1021/jacsau.4c00768","DOIUrl":"https://doi.org/10.1021/jacsau.4c00768https://doi.org/10.1021/jacsau.4c00768","url":null,"abstract":"<p >An electrochemical method for carrying out safer cyanation reactions is reported. The use of 5-aminotetrazole as a cyanide source enabled the successful electrogeneration of both electrophilic and nucleophilic cyanide sources. To demonstrate the versatility of the method, a variety of cyanation reactions were carried out, including the synthesis of cyanamides, <i>N</i>-heterocycles, and aromatic nitriles, as well as the nucleophilic addition of cyanides to a variety of electrophiles without the need to handle highly toxic cyanide salts. Finally, as a proof of concept for scalability, the cyanation methodology was rapidly transferred to a flow electrosynthesis setup, which demonstrated its potential for large-scale applications.</p>","PeriodicalId":94060,"journal":{"name":"JACS Au","volume":"4 11","pages":"4199–4205 4199–4205"},"PeriodicalIF":8.5,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/jacsau.4c00768","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142694515","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Integration of Single Atoms for Tandem Catalysis 整合单原子实现串联催化
IF 8.5 Q1 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-10-30 DOI: 10.1021/jacsau.4c0078410.1021/jacsau.4c00784
Cun Liu, Botao Qiao* and Tao Zhang*, 

Tandem catalysis represents an efficient pathway which greatly saves the overall facilities and energy inputs. The intermediates are transported from one active site to the other site more efficiently due to the ease of mass transfer in one reactor system. However, sometimes the indiscriminative usage of this concept can be misleading, and thereby, this Perspective first aims for differentiating “tandem catalysis” from liable-to-muddling concepts, such as “synergy” and “domino/cascade catalysis.” The prerequisites for figuring out tandem catalysis mainly lie in (1) the two or more independent catalytic cycles involved in one system, where the products of one reaction cycle can be immediately relayed to a subsequent reaction cycle as the reactants, and (2) these cycles occurring in different catalytic mechanisms. As a frontier in heterogeneous catalysis, single-atom catalysts possess the unique property of high selectivity toward transformation of specific chemical bonds and can also bridge the homo- and heterogeneous catalysis. However, despite their wide range of applications, single-atom catalysts (SACs) are not solutions to all catalytic processes, particularly those reactions requiring active sites containing multiatoms in their proximity. To this end, the strategy of combining SACs within tandem processes is a feasible way to broaden the scope of chemical reactions achievable over SACs. Therein, according to the category of the participating active species, four subsections are thoroughly introduced, including tandem catalysis over the integration of (1) different/identical single atom(s), (2) single atoms and nanoparticles, and (3) single atoms and the adjacent support. Nonetheless, with regard to the investigation of the involved single-atom catalysts, some issues still remain regarding the exact characterization and explicit comparison of catalytic performance with that over their nanoparticle counterparts. Moreover, some intriguing subjects are still waiting to be systematically explored to broaden and deepen single-atom-integrated tandem processes in the branch of catalytic science.

串联催化是一种高效的途径,可大大节省整体设备和能源投入。由于在一个反应器系统中易于传质,中间产物可以更高效地从一个活性位点输送到另一个位点。因此,本视角首先要将 "串联催化 "与 "协同 "和 "多米诺/级联催化 "等容易混淆的概念区分开来。弄清串联催化的前提条件主要在于:(1) 一个系统中涉及两个或多个独立的催化循环,其中一个反应循环的产物可以作为反应物立即转入下一个反应循环;(2) 这些循环发生在不同的催化机理中。作为异相催化领域的前沿技术,单原子催化剂具有对特定化学键的转化具有高选择性的独特性质,同时还能在同相催化和异相催化之间架起一座桥梁。然而,尽管单原子催化剂(SAC)应用广泛,但它并不能解决所有催化过程,尤其是那些需要活性位点邻近含有多原子的反应。为此,在串联工艺中结合单原子催化剂的策略是扩大单原子催化剂可实现的化学反应范围的可行方法。其中,根据参与的活性物种类别,详细介绍了四个小节,包括(1)不同/相同单原子、(2)单原子和纳米颗粒以及(3)单原子和相邻支持物的整合串联催化。然而,在对相关单原子催化剂的研究中,仍存在一些问题,如催化性能的准确表征和与纳米颗粒催化性能的明确比较。此外,一些引人入胜的课题仍有待系统探索,以拓宽和深化催化科学分支中的单原子集成串联过程。
{"title":"Integration of Single Atoms for Tandem Catalysis","authors":"Cun Liu,&nbsp;Botao Qiao* and Tao Zhang*,&nbsp;","doi":"10.1021/jacsau.4c0078410.1021/jacsau.4c00784","DOIUrl":"https://doi.org/10.1021/jacsau.4c00784https://doi.org/10.1021/jacsau.4c00784","url":null,"abstract":"<p >Tandem catalysis represents an efficient pathway which greatly saves the overall facilities and energy inputs. The intermediates are transported from one active site to the other site more efficiently due to the ease of mass transfer in one reactor system. However, sometimes the indiscriminative usage of this concept can be misleading, and thereby, this Perspective first aims for differentiating “tandem catalysis” from liable-to-muddling concepts, such as “synergy” and “domino/cascade catalysis.” The prerequisites for figuring out tandem catalysis mainly lie in (1) the two or more independent catalytic cycles involved in one system, where the products of one reaction cycle can be immediately relayed to a subsequent reaction cycle as the reactants, and (2) these cycles occurring in different catalytic mechanisms. As a frontier in heterogeneous catalysis, single-atom catalysts possess the unique property of high selectivity toward transformation of specific chemical bonds and can also bridge the homo- and heterogeneous catalysis. However, despite their wide range of applications, single-atom catalysts (SACs) are not solutions to all catalytic processes, particularly those reactions requiring active sites containing multiatoms in their proximity. To this end, the strategy of combining SACs within tandem processes is a feasible way to broaden the scope of chemical reactions achievable over SACs. Therein, according to the category of the participating active species, four subsections are thoroughly introduced, including tandem catalysis over the integration of (1) different/identical single atom(s), (2) single atoms and nanoparticles, and (3) single atoms and the adjacent support. Nonetheless, with regard to the investigation of the involved single-atom catalysts, some issues still remain regarding the exact characterization and explicit comparison of catalytic performance with that over their nanoparticle counterparts. Moreover, some intriguing subjects are still waiting to be systematically explored to broaden and deepen single-atom-integrated tandem processes in the branch of catalytic science.</p>","PeriodicalId":94060,"journal":{"name":"JACS Au","volume":"4 11","pages":"4129–4140 4129–4140"},"PeriodicalIF":8.5,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/jacsau.4c00784","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142694612","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Nicotinamide Riboside and CD38: Covalent Inhibition and Live-Cell Labeling 烟酰胺核苷和 CD38:共价抑制和活细胞标记
IF 8.5 Q1 CHEMISTRY, MULTIDISCIPLINARY Pub Date : 2024-10-30 DOI: 10.1021/jacsau.4c0069510.1021/jacsau.4c00695
Guoyun Kao, Xiao-Nan Zhang, Fariborz Nasertorabi, Benjamin B. Katz, Zeyang Li, Zhefu Dai, Zeyu Zhang, Lei Zhang, Stan G. Louie, Vadim Cherezov and Yong Zhang*, 

Nicotinamide adenine dinucleotide (NAD+) is required for a myriad of metabolic, signaling, and post-translational events in cells. Its levels in tissues and organs are closely associated with health conditions. The homeostasis of NAD+ is regulated by biosynthetic pathways and consuming enzymes. As a membrane-bound protein with robust NAD+ hydrolase activity, cluster of differentiation 38 (CD38) is a major degrader of NAD+. Deficiency or inhibition of CD38 enhances NAD+ levels in vivo, resulting in various therapeutic benefits. As a metabolic precursor of NAD+, nicotinamide mononucleotide can be rapidly hydrolyzed by CD38, whereas nicotinamide riboside (NR) lacks CD38 substrate activity. Given their structural similarities, we explored the inhibition potential of NR. To our surprise, NR exhibits marked inhibitory activity against CD38 by forming a stable ribosyl–ester bond with the glutamate residue 226 at the active site. Inspired by this discovery, we designed and synthesized a clickable NR featuring an azido substitution at the 5′-OH position. This cell-permeable NR analogue enables covalent labeling and imaging of both extracellular and intracellular CD38 in live cells. Our work discovers an unrecognized molecular function of NR and generates a covalent probe for health-related CD38. These findings offer new insights into the role of NR in modulating NAD+ metabolism and CD38-mediated signaling as well as an innovative tool for in-depth studies of CD38 in physiology and pathophysiology.

烟酰胺腺嘌呤二核苷酸(NAD+)是细胞中无数代谢、信号传递和翻译后活动所必需的。它在组织和器官中的含量与健康状况密切相关。NAD+ 的平衡受生物合成途径和消耗酶的调节。作为一种具有强大 NAD+ 水解酶活性的膜结合蛋白,分化簇 38(CD38)是 NAD+ 的主要降解者。缺乏或抑制 CD38 会提高体内的 NAD+ 水平,从而产生各种治疗效果。作为 NAD+ 的代谢前体,烟酰胺单核苷酸可被 CD38 快速水解,而烟酰胺核苷(NR)则缺乏 CD38 底物活性。鉴于它们的结构相似,我们对 NR 的抑制潜力进行了探索。令我们惊讶的是,NR 通过与活性位点上的谷氨酸残基 226 形成稳定的核糖酯键,对 CD38 表现出明显的抑制活性。受这一发现的启发,我们设计并合成了一种可点击的 NR,其特点是在 5′-OH位置具有叠氮取代。这种可渗透细胞的 NR 类似物可对活细胞中细胞外和细胞内的 CD38 进行共价标记和成像。我们的研究发现了 NR 的一种未被发现的分子功能,并生成了一种与健康相关的 CD38 的共价探针。这些发现提供了关于 NR 在调节 NAD+ 代谢和 CD38 介导的信号转导中的作用的新见解,同时也为深入研究 CD38 在生理学和病理生理学中的作用提供了一种创新工具。
{"title":"Nicotinamide Riboside and CD38: Covalent Inhibition and Live-Cell Labeling","authors":"Guoyun Kao,&nbsp;Xiao-Nan Zhang,&nbsp;Fariborz Nasertorabi,&nbsp;Benjamin B. Katz,&nbsp;Zeyang Li,&nbsp;Zhefu Dai,&nbsp;Zeyu Zhang,&nbsp;Lei Zhang,&nbsp;Stan G. Louie,&nbsp;Vadim Cherezov and Yong Zhang*,&nbsp;","doi":"10.1021/jacsau.4c0069510.1021/jacsau.4c00695","DOIUrl":"https://doi.org/10.1021/jacsau.4c00695https://doi.org/10.1021/jacsau.4c00695","url":null,"abstract":"<p >Nicotinamide adenine dinucleotide (NAD<sup>+</sup>) is required for a myriad of metabolic, signaling, and post-translational events in cells. Its levels in tissues and organs are closely associated with health conditions. The homeostasis of NAD<sup>+</sup> is regulated by biosynthetic pathways and consuming enzymes. As a membrane-bound protein with robust NAD<sup>+</sup> hydrolase activity, cluster of differentiation 38 (CD38) is a major degrader of NAD<sup>+</sup>. Deficiency or inhibition of CD38 enhances NAD<sup>+</sup> levels in vivo, resulting in various therapeutic benefits. As a metabolic precursor of NAD<sup>+</sup>, nicotinamide mononucleotide can be rapidly hydrolyzed by CD38, whereas nicotinamide riboside (NR) lacks CD38 substrate activity. Given their structural similarities, we explored the inhibition potential of NR. To our surprise, NR exhibits marked inhibitory activity against CD38 by forming a stable ribosyl–ester bond with the glutamate residue 226 at the active site. Inspired by this discovery, we designed and synthesized a clickable NR featuring an azido substitution at the 5′-OH position. This cell-permeable NR analogue enables covalent labeling and imaging of both extracellular and intracellular CD38 in live cells. Our work discovers an unrecognized molecular function of NR and generates a covalent probe for health-related CD38. These findings offer new insights into the role of NR in modulating NAD<sup>+</sup> metabolism and CD38-mediated signaling as well as an innovative tool for in-depth studies of CD38 in physiology and pathophysiology.</p>","PeriodicalId":94060,"journal":{"name":"JACS Au","volume":"4 11","pages":"4345–4360 4345–4360"},"PeriodicalIF":8.5,"publicationDate":"2024-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/jacsau.4c00695","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142694518","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
期刊
JACS Au
全部 Acc. Chem. Res. ACS Applied Bio Materials ACS Appl. Electron. Mater. ACS Appl. Energy Mater. ACS Appl. Mater. Interfaces ACS Appl. Nano Mater. ACS Appl. Polym. Mater. ACS BIOMATER-SCI ENG ACS Catal. ACS Cent. Sci. ACS Chem. Biol. ACS Chemical Health & Safety ACS Chem. Neurosci. ACS Comb. Sci. ACS Earth Space Chem. ACS Energy Lett. ACS Infect. Dis. ACS Macro Lett. ACS Mater. Lett. ACS Med. Chem. Lett. ACS Nano ACS Omega ACS Photonics ACS Sens. ACS Sustainable Chem. Eng. ACS Synth. Biol. Anal. Chem. BIOCHEMISTRY-US Bioconjugate Chem. BIOMACROMOLECULES Chem. Res. Toxicol. Chem. Rev. Chem. Mater. CRYST GROWTH DES ENERG FUEL Environ. Sci. Technol. Environ. Sci. Technol. Lett. Eur. J. Inorg. Chem. IND ENG CHEM RES Inorg. Chem. J. Agric. Food. Chem. J. Chem. Eng. Data J. Chem. Educ. J. Chem. Inf. Model. J. Chem. Theory Comput. J. Med. Chem. J. Nat. Prod. J PROTEOME RES J. Am. Chem. Soc. LANGMUIR MACROMOLECULES Mol. Pharmaceutics Nano Lett. Org. Lett. ORG PROCESS RES DEV ORGANOMETALLICS J. Org. Chem. J. Phys. Chem. J. Phys. Chem. A J. Phys. Chem. B J. Phys. Chem. C J. Phys. Chem. Lett. Analyst Anal. Methods Biomater. Sci. Catal. Sci. Technol. Chem. Commun. Chem. Soc. Rev. CHEM EDUC RES PRACT CRYSTENGCOMM Dalton Trans. Energy Environ. Sci. ENVIRON SCI-NANO ENVIRON SCI-PROC IMP ENVIRON SCI-WAT RES Faraday Discuss. Food Funct. Green Chem. Inorg. Chem. Front. Integr. Biol. J. Anal. At. Spectrom. J. Mater. Chem. A J. Mater. Chem. B J. Mater. Chem. C Lab Chip Mater. Chem. Front. Mater. Horiz. MEDCHEMCOMM Metallomics Mol. Biosyst. Mol. Syst. Des. Eng. Nanoscale Nanoscale Horiz. Nat. Prod. Rep. New J. Chem. Org. Biomol. Chem. Org. Chem. Front. PHOTOCH PHOTOBIO SCI PCCP Polym. Chem.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1