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Facile Synthesis of 15N-Labeled Amino Acids Using 15N-Ammonium Salt
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-27 DOI: 10.1016/j.tetlet.2025.155490
Kuga Arima, Kenichi Matsuda, Toshiyuki Wakimoto
{"title":"Facile Synthesis of 15N-Labeled Amino Acids Using 15N-Ammonium Salt","authors":"Kuga Arima,&nbsp;Kenichi Matsuda,&nbsp;Toshiyuki Wakimoto","doi":"10.1016/j.tetlet.2025.155490","DOIUrl":"10.1016/j.tetlet.2025.155490","url":null,"abstract":"<div><div><sup>15</sup>N-Labeled amino acids are utilized across a wide range of research fields in biology and chemistry. However, <sup>15</sup>N-labeled materials are typically not readily available, hindering broader applications despite their versatility. In this study, we developed a facile synthetic method for <sup>15</sup>N-labeled amino acid hydrochlorides, using a cost-effective and easy-to-handle <sup>15</sup>N-ammonium salt as the <sup>15</sup>N source. This method employs <sup>15</sup>N-labeled phthalimide as a key synthetic intermediate, which is subsequently coupled with hydroxy acid derivatives under Mitsunobu conditions to afford the corresponding amino acids, providing efficient access to various <sup>15</sup>N-labeled amino acids.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155490"},"PeriodicalIF":1.5,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150504","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Identification of a new tetrahydropyrimidine compound derived from glycation mimic reaction of spermidine and methylglyoxal in wheat germ crackers
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-27 DOI: 10.1016/j.tetlet.2025.155491
Koki Sugiura , Yuta Morishita , Yuto Shimoda , Takashi Fujimoto , Tomoyuki Fujita , Ayumi Tsutsui
{"title":"Identification of a new tetrahydropyrimidine compound derived from glycation mimic reaction of spermidine and methylglyoxal in wheat germ crackers","authors":"Koki Sugiura ,&nbsp;Yuta Morishita ,&nbsp;Yuto Shimoda ,&nbsp;Takashi Fujimoto ,&nbsp;Tomoyuki Fujita ,&nbsp;Ayumi Tsutsui","doi":"10.1016/j.tetlet.2025.155491","DOIUrl":"10.1016/j.tetlet.2025.155491","url":null,"abstract":"<div><div>Polyamines are important biological compounds. Mammals, including humans, biosynthesize polyamines in vivo or ingest them as food constituents. Spermidine is a reactive nucleophilic polyamine that reacts readily with aldehydes and carbonyls. In this study, a new tetrahydropyrimidine compound (MG-HSpd) is reported from the reaction of spermidine with methylglyoxal, a carbonyl stress substance produced by autoxidation of glucose. MG-HSpd was confirmed as a constituent of wheat germ crackers after the reaction of spermidine and methylglyoxal during the baking process.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155491"},"PeriodicalIF":1.5,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150502","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
NCBSI/TEA: A reagent system for rapid and efficient synthesis of isoxazolines from aldoxime
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-27 DOI: 10.1016/j.tetlet.2025.155489
Nilesh B. Patil , Rhutuja Patil , Ganesh U. Chaturbhuj
{"title":"NCBSI/TEA: A reagent system for rapid and efficient synthesis of isoxazolines from aldoxime","authors":"Nilesh B. Patil ,&nbsp;Rhutuja Patil ,&nbsp;Ganesh U. Chaturbhuj","doi":"10.1016/j.tetlet.2025.155489","DOIUrl":"10.1016/j.tetlet.2025.155489","url":null,"abstract":"<div><div>This report describes an efficient method for synthesizing isoxazolines from aldoximes using NCBSI as a reagent. In this protocol, <em>N</em>-chloro-<em>N</em>-(phenylsulfonyl)benzene sulfonamide (NCBSI) oxidized aldoximes into nitrile oxide. The nitrile oxide underwent 1,3-dipolar cycloaddition to alkenes, giving isoxazolines in good to excellant yields. Furthermore, the precursor <em>N</em>-(phenylsulfonyl)benzene sulfonamide was recovered and transformed to NCBSI, making the protocol eco-friendly and cost-effective.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155489"},"PeriodicalIF":1.5,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150503","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Copper-catalyzed γ-selective yne-allylic substitution of vinyl ethynylethylene carbonates towards a formal [3 + 3] cycloaddition
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-27 DOI: 10.1016/j.tetlet.2025.155487
Yu Bao, HaiHui Zhu, Hai Huang
{"title":"Copper-catalyzed γ-selective yne-allylic substitution of vinyl ethynylethylene carbonates towards a formal [3 + 3] cycloaddition","authors":"Yu Bao,&nbsp;HaiHui Zhu,&nbsp;Hai Huang","doi":"10.1016/j.tetlet.2025.155487","DOIUrl":"10.1016/j.tetlet.2025.155487","url":null,"abstract":"<div><div>Selective nonclassic propargylic substitutions have been a research focus in recent years. Herein, we developed a tandem γ-selective propargylic substitution and ring closure reaction of vinyl ethynylethylene carbonates (VEECs), efficiently synthesizing a series of 4<em>H</em>-pyran compounds. Additionally, the synthetic applications demonstrated that the products have significant synthetic potential in the synthesis of spirocyclic compounds.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155487"},"PeriodicalIF":1.5,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143132699","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Multifunctional Cys labeling-directed N-terminus-selective stapling strategy development
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-24 DOI: 10.1016/j.tetlet.2025.155480
Yabo Deng , Yisheng Cao , Yi Zhou , Zhiqiang Shen , Danna Chen , Shunqing Wang , Wenjin Yan , Jian Han , Jinqi Huang
{"title":"Multifunctional Cys labeling-directed N-terminus-selective stapling strategy development","authors":"Yabo Deng ,&nbsp;Yisheng Cao ,&nbsp;Yi Zhou ,&nbsp;Zhiqiang Shen ,&nbsp;Danna Chen ,&nbsp;Shunqing Wang ,&nbsp;Wenjin Yan ,&nbsp;Jian Han ,&nbsp;Jinqi Huang","doi":"10.1016/j.tetlet.2025.155480","DOIUrl":"10.1016/j.tetlet.2025.155480","url":null,"abstract":"<div><div>Protein bioconjugation technology integrates the fields of synthetic chemistry and molecular biology, where <em>N</em>-terminal amino groups are increasingly targeted for site-specific modification strategies due to their unique properties. Herein, we report a novel approach to achieve bioconjugation of cysteine and <em>N</em>-terminal amino groups using multifunctional allyl sulfone-activated esters. The experiments were performed in a biocompatible environment (pH 7.4, 10 mM PBS, 37 °C) with universal sequence compatibility for unprotected random peptides of different lengths. Cyclic peptides show desirable late functionalization modifications (including biotin, alkynyl, and PEG et al.).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155480"},"PeriodicalIF":1.5,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150495","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Synthesis and stability of N-ε-phospholysine derivatives
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-20 DOI: 10.1016/j.tetlet.2025.155471
Ryanne K. Ballard, Clifford E. Berkman
{"title":"Synthesis and stability of N-ε-phospholysine derivatives","authors":"Ryanne K. Ballard,&nbsp;Clifford E. Berkman","doi":"10.1016/j.tetlet.2025.155471","DOIUrl":"10.1016/j.tetlet.2025.155471","url":null,"abstract":"<div><div><em>N-ε</em>-Phosphorylated lysine (<em>p</em>Lys) residues have been understudied due to their presumed instability to withstand the conventional acidic conditions used in phosphoprotein and phosphopeptide analysis. While some efforts have been made to develop non-hydrolysable <em>p</em>Lys surrogates, less progress has been made on developing methods to prepare authentic <em>p</em>Lys residue and its derivatives. This study provides a synthetic route to <em>N-ε</em>-phosphorylated lysine models and assesses their pH-dependent stability by use of <sup>31</sup>P NMR and HPLC. While the <em>p</em>Lys models expectedly showed instability at lower pH (3.5), they showed unexpected stability in moderately acidic conditions (pH 5.0). In addition, the <em>p</em>Lys models were sufficiently stable when analyzed utilizing HPLC gradients with an acid modifier (0.1 % TFA).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155471"},"PeriodicalIF":1.5,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150497","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Rapid construction of a diterpene-inspired tetracyclic skeleton bearing bicyclo[3.2.1]octane rings based on desymmetrization of 1,3-diketones
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-19 DOI: 10.1016/j.tetlet.2025.155470
Hidetoshi Kamada, Haruki Mizoguchi, Akira Sakakura
{"title":"Rapid construction of a diterpene-inspired tetracyclic skeleton bearing bicyclo[3.2.1]octane rings based on desymmetrization of 1,3-diketones","authors":"Hidetoshi Kamada,&nbsp;Haruki Mizoguchi,&nbsp;Akira Sakakura","doi":"10.1016/j.tetlet.2025.155470","DOIUrl":"10.1016/j.tetlet.2025.155470","url":null,"abstract":"<div><div>A synthetic methodology for constructing <em>ent</em>-kaurane-like tetracyclic skeletons possessing a bicyclo[3.2.1]octane moiety has been developed by employing a desymmetrizing sequential cyclization strategy. Using a symmetric diketone as a key branching point, the sequence of desymmetric Friedel–Crafts cyclization and Pd-catalyzed intramolecular α-vinylation of ketone allowed us to construct the <em>ent</em>-kaurane-like tetracyclic skeleton from 1,3-cyclohexanedione in four steps. In contrast, reversing the order of the cyclization steps yielded a pseudo-symmetric tetracyclic skeleton, which is also reminiscent of the kaurane framework.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155470"},"PeriodicalIF":1.5,"publicationDate":"2025-01-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150494","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Visible-light-promoted trifluoromethylation/arylation of unactivated alkenes with Togni-CF3 for the synthesis of trifluoromethylated pyrrolo[1,2–a]indoles
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-18 DOI: 10.1016/j.tetlet.2025.155468
Hongni Qin , Yong Zhang , Song Sun
{"title":"Visible-light-promoted trifluoromethylation/arylation of unactivated alkenes with Togni-CF3 for the synthesis of trifluoromethylated pyrrolo[1,2–a]indoles","authors":"Hongni Qin ,&nbsp;Yong Zhang ,&nbsp;Song Sun","doi":"10.1016/j.tetlet.2025.155468","DOIUrl":"10.1016/j.tetlet.2025.155468","url":null,"abstract":"<div><div>Herein, we reported a visible-light-promoted trifluoromethylation/arylation of unactivated alkenes with Togni-CF<sub>3</sub>, leading to a series of trifluoromethylated indole-fused heterocycles in moderate to good yields. Mechanically, this reaction initiated by the radical addition of CF<sub>3</sub> radical to the alkene motif, furnishing an alkyl carbon radical, followed by its addition to the aromatic ring, and then rearomatization to afford the trifluoromethylated pyrrolo[1,2–<em>a</em>]indoles.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155468"},"PeriodicalIF":1.5,"publicationDate":"2025-01-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150493","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
A “double-locked” fluorescent probe for HClO/H2S detection
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-17 DOI: 10.1016/j.tetlet.2025.155466
Zhengkun Liu , Qianqian Wang , Wenjie Zhang , Wenyang Li , Xinyue Liu , Xiaoqiang Li , Jialong Gou
{"title":"A “double-locked” fluorescent probe for HClO/H2S detection","authors":"Zhengkun Liu ,&nbsp;Qianqian Wang ,&nbsp;Wenjie Zhang ,&nbsp;Wenyang Li ,&nbsp;Xinyue Liu ,&nbsp;Xiaoqiang Li ,&nbsp;Jialong Gou","doi":"10.1016/j.tetlet.2025.155466","DOIUrl":"10.1016/j.tetlet.2025.155466","url":null,"abstract":"<div><div>This study explores the “double-locked” probe strategy for simultaneous detection of oxidative hypochlorous acid (HClO) and reductive hydrogen sulfide (H<sub>2</sub>S). Drawing on our previous work on push–pull electronic structure-based probe <strong>Sa1</strong>, we designed and synthesized a novel double-locked probe, <strong>An1</strong>, for the simultaneous sensing of HClO and H<sub>2</sub>S. Our results demonstrate that <strong>An1</strong> remains fluorescently quenched in the presence of either HClO or H<sub>2</sub>S alone, while displaying robust fluorescence turn-on upon their coexistence. This detection mechanism is well-supported by mass spectrometry analysis. Reaction kinetics studies reveal excellent responsiveness, and selectivity experiments confirm the specific recognition of HClO and H<sub>2</sub>S. Prior to biological applications, the low cytotoxicity of <strong>An1</strong> was validated through MTT assays. Finally, the applicability of <strong>An1</strong> in biological systems was successfully demonstrated in tumor cells and zebrafish models. This work not only validates the potent double-locked detection capability of <strong>An1</strong> with potential clinical implications but also underscores the versatility of the push–pull electronic structure as a generic platform for double-locked probe design.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155466"},"PeriodicalIF":1.5,"publicationDate":"2025-01-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150499","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Silica mediated 1,6-conjugate addition of indoles and other heterocycles to p-quinone methides under solvent free condition
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-15 DOI: 10.1016/j.tetlet.2024.155398
Ramanand Das , Dip Raj Rai , Deepika Kindo , Kimron Protim Phukan , Taraknath Kundu
{"title":"Silica mediated 1,6-conjugate addition of indoles and other heterocycles to p-quinone methides under solvent free condition","authors":"Ramanand Das ,&nbsp;Dip Raj Rai ,&nbsp;Deepika Kindo ,&nbsp;Kimron Protim Phukan ,&nbsp;Taraknath Kundu","doi":"10.1016/j.tetlet.2024.155398","DOIUrl":"10.1016/j.tetlet.2024.155398","url":null,"abstract":"<div><div>Herein, we report an atom economical, operationally simple, solvent and metal-free, green synthetic method for the synthesis of triarylmethanes (TAMs) and indolyl diarylmethanes (IDMs) using commercial silica gel as recyclable solid support reagents through nucleophilic 1,6-conjugate addition of indoles to <em>p</em>-quinone methides (<em>p</em>-QMs). The method doesn’t require any additional catalyst and is compatible with a wide range of combinations of substituted <em>p</em>-QMs with indoles and other heterocycles giving good to excellent yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155398"},"PeriodicalIF":1.5,"publicationDate":"2025-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143151332","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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