ChemistryEurope最新文献_第10页

Sulfoxide-Mediated Cys-Trp-Selective Bioconjugation that Enables Protein Labeling and Peptide Heterodimerization 氧化硫介导的 Cys-Trp 选择性生物共轭，可实现蛋白质标记和肽异源二聚化

ChemistryEurope Pub Date : 2024-06-17 DOI: 10.1002/ceur.202400014

Dr. Daishiro Kobayashi, Dr. Masaya Denda, Junya Hayashi, Kota Hidaka, Yutaka Kohmura, Dr. Takaaki Tsunematsu, Dr. Kohei Nishino, Dr. Harunori Yoshikawa, Dr. Kento Ohkawachi, Dr. Kiyomi Nigorikawa, Dr. Tetsuro Yoshimaru, Prof. Naozumi Ishimaru, Prof. Wataru Nomura, Prof. Toyomasa Katagiri, Prof. Hidetaka Kosako, Prof. Akira Otaka

{"title":"Sulfoxide-Mediated Cys-Trp-Selective Bioconjugation that Enables Protein Labeling and Peptide Heterodimerization","authors":"Dr. Daishiro Kobayashi, Dr. Masaya Denda, Junya Hayashi, Kota Hidaka, Yutaka Kohmura, Dr. Takaaki Tsunematsu, Dr. Kohei Nishino, Dr. Harunori Yoshikawa, Dr. Kento Ohkawachi, Dr. Kiyomi Nigorikawa, Dr. Tetsuro Yoshimaru, Prof. Naozumi Ishimaru, Prof. Wataru Nomura, Prof. Toyomasa Katagiri, Prof. Hidetaka Kosako, Prof. Akira Otaka","doi":"10.1002/ceur.202400014","DOIUrl":"https://doi.org/10.1002/ceur.202400014","url":null,"abstract":"A method was developed that enables the magnesium chloride (MgCl2)-activated S-acetamidomethyl cysteine sulfoxide (Cys(Acm)(O)) to induce the sp2(C−H) sulfenylation of the indole of Trp residues. The reaction operates under mild acidic conditions using acetic acid or an ionic liquid to give the Trp-sulfenylated products. Other than Trp, all other proteinogenic amino acids are unreactive to the sulfenylation conditions. We demonstrated the successful application of this reaction to various peptides, including lysozyme. Furthermore, we achieved the Trp-modification of a monoclonal antibody by a MgCl2-mediated reaction in an acidic ionic liquid. The resulting antibody exhibited antibody performance comparable to the parent protein. The amide moiety in the Acm group contributes to the difference in chemical behaviors between S-Acm and S-p-methoxybenzyl (MBzl)-protected cysteine sulfoxides. This is because the S-Acm sulfoxide is converted to S-chlorocysteine responsible for Trp-sulfenylation under less acidic conditions than those required for the reaction of S-MBzl sulfoxide. Based on this rationale, we prepared a linker possessing S-Acm and S-MBzl oxide moieties and subjected the linker to heterodimerization of DNA-binding MYC and MAX peptides containing a Trp handle. The one-pot/stepwise Cys-Trp conjugation between the linker and DNA-binding peptides allowed the generation of a heterodimeric MYC/MAX DNA binder.","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"2 3-4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-06-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202400014","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141561174","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

Fluorescent Paracyclophanes: Unveiling Ultra-Strong Binding with Cucurbit[8]uril in Aqueous Environments 荧光副环烷：揭示葫芦[8]脲在水环境中的超强结合力

ChemistryEurope Pub Date : 2024-06-03 DOI: 10.1002/ceur.202400003

Laura Marie Grimm, Yichuan Wang, Amrutha Prabodh, Emma Barilli, Sebastian Spicher, Zahid Hassan, Stefan Grimme, Stefan Bräse, Frank Biedermann

{"title":"Fluorescent Paracyclophanes: Unveiling Ultra-Strong Binding with Cucurbit[8]uril in Aqueous Environments","authors":"Laura Marie Grimm, Yichuan Wang, Amrutha Prabodh, Emma Barilli, Sebastian Spicher, Zahid Hassan, Stefan Grimme, Stefan Bräse, Frank Biedermann","doi":"10.1002/ceur.202400003","DOIUrl":"10.1002/ceur.202400003","url":null,"abstract":"In supramolecular chemistry, the pursuit of highly efficient molecular recognition systems holds paramount significance. This study introduces new [2.2]paracyclophanes (PCP) as exceptional guest molecules for cucurbit[8]uril (CB8). This well-matched host-guest interaction is marked by ultra-high binding affinities (Ka up to 1015 M−1 in water) accompanied by unprecedented exothermic contributions (ΔH up to −20.6 kcal mol−1) observed in CB8 binding, rivaling the exceptional affinities of cucurbit[7]uril (CB7), which has until now been recognized as the gold standard for high-affinity binding in water. The PCPs demonstrate an excellent fit within the CB8 cavity without structural deformation of the host. Our research methodology incorporates organic synthesis, NMR, fluorescence titration, and isothermal titration calorimetry (ITC) experiments, as well as quantum mechanical simulations, to systematically examine the binding characteristics of fluorescent mono- and dicationic PCP guests within the CB8 cavity. This study not only corroborates but also critically reevaluates certain aspects of the “high-energy water release model” for cucurbit[n]uril systems. Furthermore, the ease of modifying PCP compounds, combined with their superior water solubility compared to di- and triamantanes, and their characteristic fluorescent response in forming and disassembling host-guest complexes, elevates PCPs as promising candidates for the creation of advanced supramolecular CB8-functional materials and sensing assays.","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"2 3-4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202400003","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141271296","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

Preparation of a Stable Cr2O3/Cu/TiO2 Plasmonic Photocatalyst for Selective Alcohol Oxidation under Visible Light Irradiation (λ>600 nm) 制备稳定的 Cr2O3/Cu/TiO2 等离子体光催化剂，用于在可见光照射下（λ>600 纳米）选择性氧化酒精

ChemistryEurope Pub Date : 2024-03-26 DOI: 10.1002/ceur.202400008

Dr. Atsuhiro Tanaka, Kohki Okabayashi, Ryosuke Yagi, Prof. Dr. Hiroshi Kominami

{"title":"Preparation of a Stable Cr2O3/Cu/TiO2 Plasmonic Photocatalyst for Selective Alcohol Oxidation under Visible Light Irradiation (λ>600 nm)","authors":"Dr. Atsuhiro Tanaka, Kohki Okabayashi, Ryosuke Yagi, Prof. Dr. Hiroshi Kominami","doi":"10.1002/ceur.202400008","DOIUrl":"10.1002/ceur.202400008","url":null,"abstract":"Copper (Cu) nanoparticles (NPs) loaded on titanium(IV) oxide (TiO2) exhibit an extinction at about λ=580 nm because of surface plasmon resonance (SPR); however, they rapidly lose their its SPR when exposed to air. In order to stabilize the Cu NPs, a multi-step photodeposition method was used to introduce chromium, which resulted in successful synthesis of a Cr2O3/Cu/TiO2 sample that exhibited extinction even when exposed to air. Transmission electron microscopy, scanning transmission electron microscopy, X-ray photoelectron spectroscopy and UV-vis spectroscopy were utilized to analyze the Cu/TiO2 and Cr2O3/Cu/TiO2 samples with a focus on SPR of the nanoparticles and state of the Cu species. The prepared Cr2O3/Cu/TiO2 samples acted as plasmonic photocatalysts in oxidation of 2-propanol under aerated conditions and visible light irradiation. Expandability of the Cr2O3/Cu/TiO2 plasmonic photocatalyst was also investigated, and the results suggested the potential of a Cu-based plasmonic photocatalyst working under irradiation of visible light.","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"2 3-4","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-03-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202400008","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140378761","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

Synthesis of Peptides by Reactive Extrusion. Application to the Continuous and Solventless Preparation of Aspartame. 通过反应挤压合成肽。应用于阿斯巴甜的连续无溶剂制备。

ChemistryEurope Pub Date : 2024-03-25 DOI: 10.1002/ceur.202400007

Dr. Tharwat Mohy El-Dine, Matthieu Lavayssiere, Dr. Hélène Adihou, Prof. Gilles Subra, Dr. Thomas-Xavier Métro, Dr. Olivier Ludemann-Hombourger, Dr. Frédéric Lamaty

引用次数: 0

Single-Carbon Atom Doping Reactions Using Atomic Carbon and Its Equivalents 使用原子碳及其等价物的单碳原子掺杂反应

ChemistryEurope Pub Date : 2024-03-07 DOI: 10.1002/ceur.202400005

Dr. Hayato Fujimoto, Prof. Dr. Mamoru Tobisu

引用次数: 0

Introducing Weakly Ligated Tris(trifluoromethyl)copper(III) 引入弱配位三(三氟甲基)铜(III)

ChemistryEurope Pub Date : 2024-03-01 DOI: 10.1002/ceur.202400004

Dr. Vladimir Motornov, Martin Procházka, Nora Alpuente, Dr. Pedro Salvador, Prof. Petr Slavíček, Dr. Blanka Klepetářová, Prof. Xavi Ribas, Dr. Petr Beier

{"title":"Introducing Weakly Ligated Tris(trifluoromethyl)copper(III)","authors":"Dr. Vladimir Motornov, Martin Procházka, Nora Alpuente, Dr. Pedro Salvador, Prof. Petr Slavíček, Dr. Blanka Klepetářová, Prof. Xavi Ribas, Dr. Petr Beier","doi":"10.1002/ceur.202400004","DOIUrl":"10.1002/ceur.202400004","url":null,"abstract":"Tris(trifluoromethyl)copper(III), Cu(CF3)3, was prepared for the first time and fully characterized in the form of weakly coordinated highly reactive solvent neutral adducts (DMF)2Cu(CF3)3 and (MeCN)Cu(CF3)3. Free Cu(CF3)3 is an elusive molecule of distorted T-shaped geometry with Lewis acid properties, which is stabilized by solvation. Substitution of solvent molecules with monoanionic ligands in mild conditions afforded the first Cu(III)(CF3)3 carboxylates [Cu(CF3)3(OAc)]− and [Cu(CF3)3(OBz)]− and Cu(III) nitrito complex [Cu(CF3)3(ONO)]−. An improved synthesis of valuable Grushin's trifluoromethylation reagents via the intermediacy of (MeCN)Cu(CF3)3 was developed. (DMF)2Cu(CF3)3 demonstrated promising properties in photoinduced radical C-H trifluoromethylation. Oxidation state theoretical studies showed the Cu(CF3)3 compounds to be borderline between classical Cu(III) and inverted ligand field Cu(I) assignment.","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"2 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202400004","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140091339","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

Front Cover: Switching Product Selectivity in Immobilized Tungstate Catalysts by Control of Hydrophobicity of Mesoporous Silicate Supports (ChemistryEurope 2/2024) 封面：通过控制介孔硅酸盐载体的疏水性来改变固定化钨酸盐催化剂的产品选择性（欧洲化学 2/2024 期）

ChemistryEurope Pub Date : 2024-02-29 DOI: 10.1002/ceur.202400009

Ko Kuwamoto, Dr. Masaya Okamura, Prof. Dr. Shiro Hikichi

引用次数: 0

Poly(iminoborane)s with Aromatic Side Groups: Insights into the Microstructure from Monodisperse Model Oligomers 具有芳香族侧基的聚(亚氨基硼烷)：从单分散模型低聚物洞察微观结构

ChemistryEurope Pub Date : 2024-02-29 DOI: 10.1002/ceur.202400011

Matthias Maier, Dr. Alexandra Friedrich, Johannes S. Schneider, Dr. Jan A. P. Sprenger, Jonas Klopf, Dr. Lars Fritze, Prof. Dr. Maik Finze, Prof. Dr. Holger Helten

{"title":"Poly(iminoborane)s with Aromatic Side Groups: Insights into the Microstructure from Monodisperse Model Oligomers","authors":"Matthias Maier, Dr. Alexandra Friedrich, Johannes S. Schneider, Dr. Jan A. P. Sprenger, Jonas Klopf, Dr. Lars Fritze, Prof. Dr. Maik Finze, Prof. Dr. Holger Helten","doi":"10.1002/ceur.202400011","DOIUrl":"https://doi.org/10.1002/ceur.202400011","url":null,"abstract":"An oligo(iminoborane), depicted on the cover as the dinosaur, was synthesized as part of a series of monodisperse oligo(iminoborane)s with increasing number of B=N units in the chain. Herein, the number of backbone atoms could be extended to 7 boron and 8 nitrogen atoms. This oligomer represents the longest well-defined molecular [>B=N<]x chain reported so far. The structures of the oligomers were studied by X-ray diffractometry, also providing insight into the microstructure of poly(iminoborane)s (PIBs). In their Research Article, H. Helten and co-workers describe PIBs with increased aromatic content, including the PIB with the highest molecular weight known to date. The meteorite collision visualizes TGA measurements of the polymers which lead to the formation of boron nitride. The authors would like to thank Tina Schneider for creating the cover artwork.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture>\u0000 </div>\u0000 </figure>\u0000 ","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"2 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202400011","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140135469","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

Cover Feature: Nucleobase Stacking Sustained by Pt−Pt Interactions (ChemistryEurope 2/2024) 封面专题：铂-铂相互作用维持的核碱基堆叠（欧洲化学 2/2024 期）

ChemistryEurope Pub Date : 2024-02-29 DOI: 10.1002/ceur.202400010

Dr. Carmen Lorenzo-Aparicio, Prof. Dr. Pablo García-Álvarez, Prof. Dr. Javier A. Cabeza, Prof. Dr. Mar Gómez-Gallego, Prof. Dr. Miguel A. Sierra

引用次数: 0

Lemieux-Johnson oxidation with N,N-bidentate bisPYA ruthenium complexes: insights into reaction conditions and catalyst design 用 N,N-二叉双PYA 钌络合物进行莱米厄-约翰逊氧化反应：对反应条件和催化剂设计的见解

ChemistryEurope Pub Date : 2024-02-29 DOI: 10.1002/ceur.202300070

Dr. Kevin Salzmann, Dr. Candela Segarra, Dr. Aline Carrel, Prof. Dr. Martin Albrecht

{"title":"Lemieux-Johnson oxidation with N,N-bidentate bisPYA ruthenium complexes: insights into reaction conditions and catalyst design","authors":"Dr. Kevin Salzmann, Dr. Candela Segarra, Dr. Aline Carrel, Prof. Dr. Martin Albrecht","doi":"10.1002/ceur.202300070","DOIUrl":"https://doi.org/10.1002/ceur.202300070","url":null,"abstract":"The carbonyl group is arguably the most versatile functional group for synthetic purposes. Here, a series of N,N’-bis(pyridylideneamide) (bisPYA) complexes of ruthenium(II), [Ru(cym)(bisPYA)Cl]+ (cym=cymene), were synthesized and applied as catalysts for Lemieux-Johnson oxidation of alkenes to access carbonyl functionalities. Complexes bearing para- and ortho-bisPYA ligands induce higher activity and selectivity than their mesoionic meta-bisPYA analogues. The non-coordinating counterion of the cationic complexes affects the catalytic performance markedly, with PF6− enhancing the activity compared to trifluoromethanesulfonate, OTf−. Likewise, replacing the anionic ancillary chloride ligand by a neutral and more labile MeCN ligand led to increased activity. Electrochemical and solubility measurements revealed no direct correlation of ligand donor strength to catalytic performance. Variation of the solvent mixture and the ratio of its components provided access to high-performance catalysts. In H2O/MeCN/CH2Cl2 at 3 : 1:0.5 (v/v) ratio, turnover frequencies up to 10,000 h−1 were obtained for the Lemieux-Johnson oxidation of styrene with these Ru(bisPYA) complexes, allowing quantitative conversions within 30 min at 0.1 mol % catalyst loadings and corresponding to a 5 times faster reaction than the best catalyst known to date for this transformation.","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"2 2","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-02-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202300070","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140135471","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