Organic & Biomolecular Chemistry最新文献

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Organocatalytic SuFEx click reactions of SO2F2.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-12-23 DOI: 10.1039/d4ob01844c
Yu Xie, Muze Lin, Zhihang Wei, Zhihua Cai, Lin He, Guangfen Du
{"title":"Organocatalytic SuFEx click reactions of SO<sub>2</sub>F<sub>2</sub>.","authors":"Yu Xie, Muze Lin, Zhihang Wei, Zhihua Cai, Lin He, Guangfen Du","doi":"10.1039/d4ob01844c","DOIUrl":"https://doi.org/10.1039/d4ob01844c","url":null,"abstract":"<p><p>An organocatalytic method for the SuFEx click reaction of gaseous SO<sub>2</sub>F<sub>2</sub> is described. Different organic bases such as DBU, TBD, triethylamine and Hünig's base can efficiently catalyze the SuFEx of SO<sub>2</sub>F<sub>2</sub> with various phenols to produce aryl fluorosulfates in 61-97% yields. Under the same conditions, pyridone, pyrazolone and amines can also react with SO<sub>2</sub>F<sub>2</sub> to afford the corresponding heteroaryl fluorosulfates or sulfamoyl fluorides in good yields. In this process, molecular sieves absorb the acidic HF efficiently, avoiding the use of stoichiometric amounts of organosilicon reagents and excess bases.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142875561","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Development of urea-bridged cyclic dominant negative pneumococcus competence-stimulating peptide analogs.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-12-23 DOI: 10.1039/d4ob01524j
Mona Mehrani, Muralikrishna Lella, Katherine A Graham, Nicholas B Borotto, Yftah Tal-Gan
{"title":"Development of urea-bridged cyclic dominant negative pneumococcus competence-stimulating peptide analogs.","authors":"Mona Mehrani, Muralikrishna Lella, Katherine A Graham, Nicholas B Borotto, Yftah Tal-Gan","doi":"10.1039/d4ob01524j","DOIUrl":"https://doi.org/10.1039/d4ob01524j","url":null,"abstract":"<p><p>Cyclization is a widely used approach to exert conformational restraint on linear peptide sequences. Herein, urea bridge chemistry was deployed to achieve side chain-to-side chain peptide cyclization on the <i>Streptococcus pneumoniae</i> CSP1-E1A peptide scaffold. To determine the effects of ring size and bridge position on the overall peptide conformation and find the ideal area within the CSP sequence for cyclization, we performed biological evaluation as well as secondary structure analysis on all the cyclic analogs. Biological evaluation results exhibited that even minor modifications to cyclic analogs for each of the cyclization positions could significantly alter the interaction between the peptide and its target receptor, ComD. Furthermore, structural analysis using circular dichroism (CD) and Trapped Ion Mobility Spectrometry (TIMS) emphasized the significance of incorporating the bridge position as a parameter to be modified, in addition to the traditional ring position and ring size parameters. Overall, our results showcase the importance of comprehensive conformational screening in fine-tuning the secondary structure of cyclic peptide analogs. This knowledge could be very useful for future studies aimed at optimizing peptide : protein interactions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142875550","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Catalyst-free coupling of peroxypyrroloindolenines with amines to afford stable peroxyindolenines.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-12-23 DOI: 10.1039/d4ob01736f
Xiaoshan Zheng, Menghan Wang, Xianbin Sun, Yu Gao, Haijun Chen
{"title":"Catalyst-free coupling of peroxypyrroloindolenines with amines to afford stable peroxyindolenines.","authors":"Xiaoshan Zheng, Menghan Wang, Xianbin Sun, Yu Gao, Haijun Chen","doi":"10.1039/d4ob01736f","DOIUrl":"https://doi.org/10.1039/d4ob01736f","url":null,"abstract":"<p><p>Here we report a highly efficient method for coupling of peroxypyrroloindolenines with amines under catalyst-free conditions to obtain stable C2-N peroxyindolenines in high yields with remarkable functional group tolerance. Initial studies have shown that compound 13 exhibits potent inhibition of the B16/F10 cell line with an IC<sub>50</sub> value of 2.18 μM.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142875542","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Aluminum-catalyzed anti-Markovnikov hydroamination of aromatic alkenes with aromatic amines.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-12-23 DOI: 10.1039/d4ob01820f
Wenliang Yan, Xiaoli Ma, Qifeng Li, Ziyuan Pang, Xiaobo Yang, Yiwen Chen, Zhi Yang
{"title":"Aluminum-catalyzed anti-Markovnikov hydroamination of aromatic alkenes with aromatic amines.","authors":"Wenliang Yan, Xiaoli Ma, Qifeng Li, Ziyuan Pang, Xiaobo Yang, Yiwen Chen, Zhi Yang","doi":"10.1039/d4ob01820f","DOIUrl":"https://doi.org/10.1039/d4ob01820f","url":null,"abstract":"<p><p>Herein, we report a novel Al compound supported by a NacNac ligand that facilitates the anti-Markovnikov hydroamination of aromatic alkenes and primary amines. This represents the first instance of an aluminum-catalyzed intermolecular hydroamination of alkenes, successfully synthesizing a variety of aromatic imine derivatives. The proposed mechanism suggests that the coordination activation of <sup><i>t</i></sup>BuOK by ether solvents is crucial, allowing the <sup><i>t</i></sup>BuO<sup>-</sup> anion to coordinate with the catalyst's Al center, thus forming a key intermediate.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142875539","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
ESIPT fluorescence turn-on sensors for detection of short chain inorganic polyphosphate in water.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-12-23 DOI: 10.1039/d4ob01926a
Subhra Kanti Roy, Sandra Moser, Tobias Dürr-Mayer, Rahel Hinkelmann, Henning J Jessen
{"title":"ESIPT fluorescence turn-on sensors for detection of short chain inorganic polyphosphate in water.","authors":"Subhra Kanti Roy, Sandra Moser, Tobias Dürr-Mayer, Rahel Hinkelmann, Henning J Jessen","doi":"10.1039/d4ob01926a","DOIUrl":"https://doi.org/10.1039/d4ob01926a","url":null,"abstract":"<p><p>We introduce two water-soluble excited state intramolecular proton transfer (ESIPT) based fluorescent turn-on probes responding to inorganic polyphosphates. These ESIPT probes enable specific detection of short-chain inorganic polyphosphates over a range of different condensed phosphates. The probes are weakly emissive in their off-state due to the blocking of ESIPT by Cu<sup>2+</sup> coordination. Removal of the copper ion through decomplexation by the analyte accesses the on-state. The probes detect polyphosphates over other biologically occurring phosphates, pyrophosphate, and nucleotides such as ATP, ADP, GTP. An optimal fluorescence response is observed with the short-chain polyphosphate polyP<sub>8</sub>. Furthermore, the probe shows selectivity towards linear polyphosphates over cyclic metaphosphates. The rapid 'turn-off-turn-on' fluorescence responses upon consecutive addition of Cu<sup>2+</sup> and polyP<sub>8</sub> are reversible, further highlighting sensor performance in an aqueous environment. One of the sensors is then used to monitor polyP digestion by an exopolyphosphatase (PPX).</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142875556","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Submicromolar fluorescence 'turn-on' detection of fluoride anions using meso-(tetra-aryl) calix[4]pyrrole.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-12-23 DOI: 10.1039/d4ob01708k
Anik Roy, Ranjan Dutta, Dibakar Halder, Koushik Mandal, Somenath Kundu, Maidul Hossain, Indrajit Saha, Chang-Hee Lee
{"title":"Submicromolar fluorescence 'turn-on' detection of fluoride anions using <i>meso</i>-(tetra-aryl) calix[4]pyrrole.","authors":"Anik Roy, Ranjan Dutta, Dibakar Halder, Koushik Mandal, Somenath Kundu, Maidul Hossain, Indrajit Saha, Chang-Hee Lee","doi":"10.1039/d4ob01708k","DOIUrl":"https://doi.org/10.1039/d4ob01708k","url":null,"abstract":"<p><p><i>Meso</i>-(tetra-aryl) picket calix[4]pyrrole 1 featuring <i>p</i>-fluorophenyl groups at all four <i>meso</i>-positions in a <i>cis</i>-configuration has been synthesized and characterized unambiguously using single-crystal X-ray diffraction analysis. This pre-organized system possesses a deep binding pocket created by the four aryl groups so that anions can be accommodated through anion-π interactions and four-point N-H⋯anion hydrogen bonds. Single-crystal X-ray diffraction analysis of the CsF and TEAF (TEA = tetraethylammonium) complexes of receptor 1 unequivocally confirms the formation of 1 : 1 complexes, revealing the binding modes in the solid state. The anion binding studies conducted in acetonitrile confirmed that the receptor forms stable 1/1 complexes with fluoride anions and coumarin anion 2- in solution. The host-coumarin ensemble 3 was then applied for the detection of fluoride anions through a fluorescent dye displacement assay (FDDA). The highly fluorescent coumarin anion becomes completely non-fluorescent upon complexation with receptor 1, and its fluorescence is recovered in a concentration-dependent manner upon the addition of fluoride anions. This system proves to be an excellent 'turn-on' sensor for detecting fluoride anions with high selectivity and sensitivity, with a detection limit for fluoride anions estimated at 177 nM.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-12-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142875564","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Origins of the substituent effects in the aldol condensation of axially chiral thiohydantoins: a computational study.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-12-20 DOI: 10.1039/d4ob01904k
Nazli Goksel Carpa, Zekihan Ozerdem, Ilknur Dogan, Zeynep Pinar Haslak, Viktorya Aviyente
{"title":"Origins of the substituent effects in the aldol condensation of axially chiral thiohydantoins: a computational study.","authors":"Nazli Goksel Carpa, Zekihan Ozerdem, Ilknur Dogan, Zeynep Pinar Haslak, Viktorya Aviyente","doi":"10.1039/d4ob01904k","DOIUrl":"https://doi.org/10.1039/d4ob01904k","url":null,"abstract":"<p><p>Aldol reactions are one of the most fundamental organic reactions involving the formation of carbon-carbon bonds that are commonly used in the synthesis of complex molecules through the condensation of an enol or enolate with a carbonyl group. The aldol reaction of thiohydantoin derivatives with benzaldehyde starts with hydrogen removal from C5 by lithium diisopropylamide (LDA) to form the enolate. Benzaldehyde adds to the enolate either at the less or more hindered site. The formed products have 3 chiral centers; thus they exist in 8 isomeric forms, RMS*/SPR*, RMR*/SPS*, SMR*/RPS*, and SMS*/RPR*, which are enantiomeric couples. Experimentally the axial chirality of the reactant is protected throughout the reaction; if the starting thiohydantoin is the M isomer, only RMS*, RMR*, SMR*, and SMS* diastereomers can be obtained. In this study, we aim to report a theoretical study of the aldol reactions between benzaldehyde and thiohydantoin derivatives conducted at the M06-2X/6-311+G(d,p) level of theory using the CPCM solvation model for THF as solvent, at 195 K. The investigation of the effect of substituents at C5 (stereocenter) and X positions on selectivity was performed by varying the substituents RCH<sub>3</sub>, XCF<sub>3</sub>; RCH<sub>3</sub>, XCl; RCH<sub>2</sub>Ph, XCF<sub>3</sub>; RCH(CH<sub>3</sub>)<sub>2</sub>, and XCF<sub>3</sub>. Agreement of calculations (M06-2X/6-311+G(d,p)/CPCM(THF)) with experiment suggests that the enantioselectivity is predominantly governed by thermodynamic control.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142862606","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Continuous flow synthesis of alkynes from isoxazolones.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-12-20 DOI: 10.1039/d4ob01772b
Aisling Loftus, Rosa De Gregorio, Marcus Baumann
{"title":"Continuous flow synthesis of alkynes from isoxazolones.","authors":"Aisling Loftus, Rosa De Gregorio, Marcus Baumann","doi":"10.1039/d4ob01772b","DOIUrl":"https://doi.org/10.1039/d4ob01772b","url":null,"abstract":"<p><p>The development of a continuous flow approach for the generation of alkynes from isoxazolones under diazotisation conditions is reported. The underlying transformation has been known for several decades; however, in batch mode, it is plagued by variable yields, excessive use of sodium nitrite and limited scalability due to its exothermic nature and the release of copious amounts of toxic nitroxide gases. The presented flow approach overcomes these limitations and delivers various alkyne products in residence times of less than 1 minute with productivities of <i>ca.</i> 2 g h<sup>-1</sup>. This demonstrates the value of continuous flow processing in miniaturised devices and renders this alkyne forming method an attractive addition to the limited synthetic toolbox towards this important functional group.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142862604","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Organo-photocatalytic dearomative hydrosilylation of indoles with silanes.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-12-20 DOI: 10.1039/d4ob01792g
Qiao Zhang, Yadi Xu, Congjian Xia, Wengang Xu, Mingbo Wu
{"title":"Organo-photocatalytic dearomative hydrosilylation of indoles with silanes.","authors":"Qiao Zhang, Yadi Xu, Congjian Xia, Wengang Xu, Mingbo Wu","doi":"10.1039/d4ob01792g","DOIUrl":"https://doi.org/10.1039/d4ob01792g","url":null,"abstract":"<p><p>A photocatalytic dearomative hydrosilylation reaction of indole derivatives with silanes has been accomplished for the synthesis of valuable indolinyl silanes through a carbon-silyl radical coupling process with the cooperation of photoredox and hydrogen atom transfer catalytic systems composed of 3DPA2FBN (2,4,6-tris(diphenylamino)-3,5-difluorobenzonitrile), (i-Pr)<sub>3</sub>SiSH, and base additives. This protocol is featured by a broad substrate scope, transition metal-free conditions, high diastereoselectivities and applications in natural product derivatives.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142862605","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
TFA-catalyzed solvent-free dearomative cyanidation of isoquinoline using (Boc)2O as an acylation agent.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-12-20 DOI: 10.1039/d4ob01849d
Xujin Zhang, Lihua Huang, Ye Zhang, Fanhua Meng, Xiandong Dai, Chunru Cheng, Yongbiao Guo, Zhenhua Gao
{"title":"TFA-catalyzed solvent-free dearomative cyanidation of isoquinoline using (Boc)<sub>2</sub>O as an acylation agent.","authors":"Xujin Zhang, Lihua Huang, Ye Zhang, Fanhua Meng, Xiandong Dai, Chunru Cheng, Yongbiao Guo, Zhenhua Gao","doi":"10.1039/d4ob01849d","DOIUrl":"https://doi.org/10.1039/d4ob01849d","url":null,"abstract":"<p><p>A TFA-catalyzed dearomative cyanidation of isoquinoline is described, which provides a series of 1-cyanoisoquinolines in high yields under solvent-free conditions. This protocol is operated under mild and environmentally friendly conditions, utilizing readily available and cost-effective starting materials. The reaction features broad functional group compatibility, 100 mmol scale synthesis ability and operational simplicity, making it a significant potential approach for the synthesis of various biologically interesting isoquinolines <i>via</i> α C-cyanation.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2024-12-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142862607","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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