Organic & Biomolecular Chemistry最新文献

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

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":"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 Streptococcus pneumoniae 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.","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

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

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":"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 Cu2+ 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 polyP8. Furthermore, the probe shows selectivity towards linear polyphosphates over cyclic metaphosphates. The rapid 'turn-off-turn-on' fluorescence responses upon consecutive addition of Cu2+ and polyP8 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).","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 meso-(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":"Meso-(tetra-aryl) picket calix[4]pyrrole 1 featuring p-fluorophenyl groups at all four meso-positions in a cis-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.","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":"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CH3, XCF3; RCH3, XCl; RCH2Ph, XCF3; RCH(CH3)2, and XCF3. Agreement of calculations (M06-2X/6-311+G(d,p)/CPCM(THF)) with experiment suggests that the enantioselectivity is predominantly governed by thermodynamic control.","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

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

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

引用次数: 0