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Recent trends in the identification and engineering of halogenases 卤素酶鉴定和工程设计的最新趋势
Tetrahedron chem Pub Date : 2024-11-19 DOI: 10.1016/j.tchem.2024.100112
Huibin Wang , Ikuro Abe
{"title":"Recent trends in the identification and engineering of halogenases","authors":"Huibin Wang ,&nbsp;Ikuro Abe","doi":"10.1016/j.tchem.2024.100112","DOIUrl":"10.1016/j.tchem.2024.100112","url":null,"abstract":"<div><div>Halogenation significantly enhances the biological activity, stability, and solubility of organic molecules, and thus is a crucial modification in the biotechnology and pharmaceutical industries. Halogenases, the core enzymes responsible for this transformation, are invaluable tools for the selective incorporation of halogens into diverse substrates, offering vast potential in drug development and synthetic biology. Recent discoveries of novel classes of halogenases have substantially expanded the repertoire of enzymatic halogenation. In parallel, remarkable progress in the protein engineering of halogenases is leading to unprecedented opportunities in the synthesis of novel compounds. These efforts have not only expanded the substrate scope, improved the selectivity, and enhanced the catalytic activity but also demonstrated their capacity for new-to-nature reactions. This perspective article highlights critical developments in the identification and engineering of halogenases, underscoring their growing significance in biocatalysis and sustainable chemical production. Continued exploration of novel halogenases, coupled with advanced protein engineering strategies, will open new frontiers in biocatalyst development and drug discovery.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100112"},"PeriodicalIF":0.0,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142705642","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
Tyrosine bioconjugation using stably preparable urazole radicals 利用可稳定制备的脲唑自由基进行酪氨酸生物键合
Tetrahedron chem Pub Date : 2024-11-19 DOI: 10.1016/j.tchem.2024.100111
Shinichi Sato , Shogo Miyano , Keita Nakane , Zhengyi Liu , Munehiro Kumashiro , Tomohide Saio , Yuya Tanaka , Akira Shigenaga , Chizu Fujimura , Eri Koyanagi , Hafumi Nishi , Shusuke Tomoshige , Minoru Ishikawa
{"title":"Tyrosine bioconjugation using stably preparable urazole radicals","authors":"Shinichi Sato ,&nbsp;Shogo Miyano ,&nbsp;Keita Nakane ,&nbsp;Zhengyi Liu ,&nbsp;Munehiro Kumashiro ,&nbsp;Tomohide Saio ,&nbsp;Yuya Tanaka ,&nbsp;Akira Shigenaga ,&nbsp;Chizu Fujimura ,&nbsp;Eri Koyanagi ,&nbsp;Hafumi Nishi ,&nbsp;Shusuke Tomoshige ,&nbsp;Minoru Ishikawa","doi":"10.1016/j.tchem.2024.100111","DOIUrl":"10.1016/j.tchem.2024.100111","url":null,"abstract":"<div><div>Our <em>ex situ</em> tyrosine bioconjugation method utilizes the oxidation of <em>N</em>-methylurazole by Bobbitt's salt or electrochemical activation to generate stable radicals for selective tyrosine labeling, thereby addressing the longstanding challenges in protein bioconjugation. Unlike traditional tyrosine conjugation techniques that rely on closed-shell chemistry with 1,2,4-triazoline-3,5-dione derivatives, this method introduces an alternative bond-forming mechanism that expands bioconjugation through a radical-based pathway that enhances tyrosine selectivity. The applicability of this method was demonstrated for various proteins and validated through proteome-wide analyses, highlighting its potential as a valuable tool for investigating protein function and interaction dynamics.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100111"},"PeriodicalIF":0.0,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142705643","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
A modern approach to intermittent illumination for the characterization of chain-propagation in photoredox catalysis 间歇照明用于表征光氧化催化过程中链式传播的现代方法
Tetrahedron chem Pub Date : 2024-11-12 DOI: 10.1016/j.tchem.2024.100110
K.A. Viraj Miyuranga , Kaitlin E. Ashcraft , Spencer P. Pitre
{"title":"A modern approach to intermittent illumination for the characterization of chain-propagation in photoredox catalysis","authors":"K.A. Viraj Miyuranga ,&nbsp;Kaitlin E. Ashcraft ,&nbsp;Spencer P. Pitre","doi":"10.1016/j.tchem.2024.100110","DOIUrl":"10.1016/j.tchem.2024.100110","url":null,"abstract":"<div><div>Photoredox catalysis has become an invaluable tool for the construction of organic molecules, allowing for unparalleled control over radical intermediates enabled by the mild conditions achieved through visible-light activation of a photocatalyst. These reactions can be classified under two distinct mechanistic paradigms: closed photocatalytic cycles, and photoinitiated chain reactions. While optimization strategies for each of these classes of reaction differ significantly, organic chemists still lack a straightforward means for probing chain-propagation. In this work, we report a simple and accessible approach to performing intermittent illumination studies for characterizing chain reactions in photoredox catalysis. Using modern LED technologies to precisely control the rate of sample illumination, we were able to validate the presence or absence of product-forming chain reactions in four previously reported photoredox protocols. Furthermore, this technique also allows for the determination of chain-propagating lifetimes through a simple graphical analysis. Given the operational simplicity and ease of accessibility, we believe this intermittent illumination technique will be of great value to practitioners of the field moving forward.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100110"},"PeriodicalIF":0.0,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142653834","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
Recent advances in catalytic carbofluorination of unsaturated system via C–F bond reconstruction 通过 C-F 键重构催化不饱和体系羧基氟化的最新进展
Tetrahedron chem Pub Date : 2024-11-06 DOI: 10.1016/j.tchem.2024.100109
Yaxin Zeng, Xufei Yan, Ying Xia
{"title":"Recent advances in catalytic carbofluorination of unsaturated system via C–F bond reconstruction","authors":"Yaxin Zeng,&nbsp;Xufei Yan,&nbsp;Ying Xia","doi":"10.1016/j.tchem.2024.100109","DOIUrl":"10.1016/j.tchem.2024.100109","url":null,"abstract":"<div><div>The distinctive properties of the fluorine atom confer significant advantages to organofluorine compounds in pharmaceuticals, agrochemicals, and materials science. A particularly promising approach for synthesizing these compounds involves atom-economical carbofluorination reactions. These reactions involve the activation of a carbon-fluorine (C–F) bond, then facilitating the incorporation of both a carbon-based fragment and a fluorine atom into an unsaturated system. The capacity to reintegrate the fluorine atom from the starting material into the final product, known as fluoride recycling via C–F bond reconstruction, is advantageous in terms of both atom and step economy. This review highlights recent advancements in catalytic C–F bond reconstruction, encompassing the background, chemical transformations, reaction scope, synthetic applications, mechanisms, and future research directions.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100109"},"PeriodicalIF":0.0,"publicationDate":"2024-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142653833","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
Efficient construction of a quinoline framework from alcohols, nitroarenes, and alkenes promoted by a trimetallic catalyst system 在三金属催化剂体系的促进下，从醇、硝基烯烃和烯烃中高效构建喹啉框架
Tetrahedron chem Pub Date : 2024-11-02 DOI: 10.1016/j.tchem.2024.100108
Rikiya Horikawa , Gen Onodera , Tsutomu Fukuda , Masanari Kimura
{"title":"Efficient construction of a quinoline framework from alcohols, nitroarenes, and alkenes promoted by a trimetallic catalyst system","authors":"Rikiya Horikawa ,&nbsp;Gen Onodera ,&nbsp;Tsutomu Fukuda ,&nbsp;Masanari Kimura","doi":"10.1016/j.tchem.2024.100108","DOIUrl":"10.1016/j.tchem.2024.100108","url":null,"abstract":"<div><div>A Pd/Fe/In-trimetallic catalyst system promotes the three-component coupling reaction of primary alcohols, nitroarenes, and terminal alkenes to construct quinoline frameworks in a single operation. These consecutive coupling reactions proceed via an oxidative Povarov reaction of alkenes and aldimines derived from primary alcohols and nitroarenes by a redox hydrogen transfer system. This reaction may contribute to the efficient development of pharmaceuticals and medicinal products.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100108"},"PeriodicalIF":0.0,"publicationDate":"2024-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142592932","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
Palladium iodide catalyzed oxidative carbonylations 碘化钯催化氧化羰基化反应
Tetrahedron chem Pub Date : 2024-11-01 DOI: 10.1016/j.tchem.2024.100107
Bartolo Gabriele
{"title":"Palladium iodide catalyzed oxidative carbonylations","authors":"Bartolo Gabriele","doi":"10.1016/j.tchem.2024.100107","DOIUrl":"10.1016/j.tchem.2024.100107","url":null,"abstract":"<div><div>Since the first publication in 1992, the PdI<sub>2</sub>/KI-catalyzed oxidative carbonylation reaction has emerged as a powerful methodology for the multicomponent and sustainable synthesis of high value added carbonylated compounds (esters, amides, lactones, lactams, ureas, oxazolidinones, cyclic carbonates, and so on) starting from simple feedstocks (alkynes, alcohols, amines, etc) in combination with carbon monoxide as the simplest and atom-economical source of the carbonyl group. The main feature of this methodology is related to the possibility to catalytically assembly several simple units in an ordered sequence to produce carbonylated derivatives in a selective way under conditions that employ the greenest and most convenient oxidation agent available (that is, oxygen from air) with formation of water as benign coproduct.</div><div>In this Review, I will illustrate the achievements that have been realized in this exciting field of research in the course of the years.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100107"},"PeriodicalIF":0.0,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142721559","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
Electrochemical dibromoacetoxylation and trihalogenation of allylarenes 烯丙基醚的电化学二溴乙酰氧基化和三卤化反应
Tetrahedron chem Pub Date : 2024-10-28 DOI: 10.1016/j.tchem.2024.100106
Yong Jiang , Fumei Ke , Chen Zhu , Daixi Li , Tao Shen
{"title":"Electrochemical dibromoacetoxylation and trihalogenation of allylarenes","authors":"Yong Jiang ,&nbsp;Fumei Ke ,&nbsp;Chen Zhu ,&nbsp;Daixi Li ,&nbsp;Tao Shen","doi":"10.1016/j.tchem.2024.100106","DOIUrl":"10.1016/j.tchem.2024.100106","url":null,"abstract":"<div><div>Trifunctionalization serves as an efficient method for rapidly enhancing molecular complexity by incorporating three functional groups from simple, readily available raw materials. Herein, we describe an electrochemical trifunctionalization protocol for allylarenes that enables the synthesis of a diverse range of dibromoacetoxylated and trihalogenated products. Further gram-scale synthesis and divergent transformation of products demonstrate potential application in the pharmaceutical industry. Mechanistic studies reveal the process involves a cascade oxidative difunctionalization of C<img>C bond and oxidative functionalization of benzylic C–H bond.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100106"},"PeriodicalIF":0.0,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142560584","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
Triquinane based natural products via cycloadditions and metathesis 通过环加成和偏合成获得基于三喹烷的天然产品
Tetrahedron chem Pub Date : 2024-10-25 DOI: 10.1016/j.tchem.2024.100103
Subba Rao Cheekatla
{"title":"Triquinane based natural products via cycloadditions and metathesis","authors":"Subba Rao Cheekatla","doi":"10.1016/j.tchem.2024.100103","DOIUrl":"10.1016/j.tchem.2024.100103","url":null,"abstract":"<div><div>Triquinane natural products are an interesting class of polycyclic frameworks that have attracted considerable interest because of their distinct structures and diverse array of biological applications such as antibacterial, antifungal, and anticancer properties and biological diversity of these scaffolds make them promising candidates for drug discovery and medicinal chemistry. These frameworks have a central structure of bicyclo[2.2.1]heptane ring which is linked to another cycloalkane ring generating the a unique tricyclic arrangement. The design and synthesis of triquinane framework is very challenging because of their intricate three-dimensional structure and the requirement for accurate organization of numerous stereocenters. Based on thorough review of literature, cycloadditions and metathesis play a pivotal role for constructing these exciting class of complex frameworks in an efficient and selective manner. In this review we focused mainly on how cycloadditions and metathesis strategies are significant in total synthesis of these interesting class of scaffolds. Here, we summarized the synthetic strategies of linear, angular, and propellane types of triquinane natural products <em>via</em> different cycloaddition protocols as well as photothermal and olefin metathesis which are used as key steps in the total synthesis.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100103"},"PeriodicalIF":0.0,"publicationDate":"2024-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142551884","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
Automation in electrifying flow organic synthesis 电气化流动有机合成的自动化
Tetrahedron chem Pub Date : 2024-10-24 DOI: 10.1016/j.tchem.2024.100105
Tomas Hardwick, Nisar Ahmed
{"title":"Automation in electrifying flow organic synthesis","authors":"Tomas Hardwick,&nbsp;Nisar Ahmed","doi":"10.1016/j.tchem.2024.100105","DOIUrl":"10.1016/j.tchem.2024.100105","url":null,"abstract":"<div><div>Organic electrochemical synthesis may be combined with continuous flow and automation technology. Here, the authors highlight the benefits of such chemical engineering approaches along with technology and software directions taking organic chemistry into the future.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100105"},"PeriodicalIF":0.0,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142538832","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
Pd(II)-catalyzed C–H annulation and lactonization of indole-2-carboxamides with hydroxyalkynoates using air as an oxidant 以空气为氧化剂催化吲哚-2-甲酰胺与羟基炔酸盐的 C-H 环化和内酯化反应
Tetrahedron chem Pub Date : 2024-10-19 DOI: 10.1016/j.tchem.2024.100104
Kiran Aswale , Rajashaker Bantu , B. Sridhar , B.V. Subba Reddy
{"title":"Pd(II)-catalyzed C–H annulation and lactonization of indole-2-carboxamides with hydroxyalkynoates using air as an oxidant","authors":"Kiran Aswale ,&nbsp;Rajashaker Bantu ,&nbsp;B. Sridhar ,&nbsp;B.V. Subba Reddy","doi":"10.1016/j.tchem.2024.100104","DOIUrl":"10.1016/j.tchem.2024.100104","url":null,"abstract":"<div><div>A novel palladium(II) catalyzed C–H annulation strategy has been developed for the synthesis of a diverse range of furo[3′,4':5,6]pyrido[3,4-<em>b</em>]indole-1,5(3<em>H</em>)-dione scaffolds. This is the first report on the construction of polycyclic carboline frameworks from indole-2-carboxamides and 4-hydroxy-2-alkynoates. This method provides a direct access to fused carbolines that are closely resemble to biologically active <em>β</em>-carboline frameworks.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100104"},"PeriodicalIF":0.0,"publicationDate":"2024-10-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142578720","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
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