Chemical ReviewsPub Date : 2024-12-10DOI: 10.1021/acs.chemrev.4c00264
Daiana A. Capdevila, Johnma J. Rondón, Katherine A. Edmonds, Joseph S. Rocchio, Matias Villarruel Dujovne, David P. Giedroc
{"title":"Bacterial Metallostasis: Metal Sensing, Metalloproteome Remodeling, and Metal Trafficking","authors":"Daiana A. Capdevila, Johnma J. Rondón, Katherine A. Edmonds, Joseph S. Rocchio, Matias Villarruel Dujovne, David P. Giedroc","doi":"10.1021/acs.chemrev.4c00264","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00264","url":null,"abstract":"Transition metals function as structural and catalytic cofactors for a large diversity of proteins and enzymes that collectively comprise the metalloproteome. Metallostasis considers all cellular processes, notably metal sensing, metalloproteome remodeling, and trafficking (or allocation) of metals that collectively ensure the functional integrity and adaptability of the metalloproteome. Bacteria employ both protein and RNA-based mechanisms that sense intracellular transition metal bioavailability and orchestrate systems-level outputs that maintain metallostasis. In this review, we contextualize metallostasis by briefly discussing the metalloproteome and specialized roles that metals play in biology. We then offer a comprehensive perspective on the diversity of metalloregulatory proteins and metal-sensing riboswitches, defining general principles within each sensor superfamily that capture how specificity is encoded in the sequence, and how selectivity can be leveraged in downstream synthetic biology and biotechnology applications. This is followed by a discussion of recent work that highlights selected metalloregulatory outputs, including metalloproteome remodeling and metal allocation by metallochaperones to both client proteins and compartments. We close by briefly discussing places where more work is needed to fill in gaps in our understanding of metallostasis.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"8 1","pages":""},"PeriodicalIF":62.1,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142805266","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-12-06DOI: 10.1021/acs.chemrev.4c00858
Jessica Wu, Katherine L. Verboom, Michael J. Krische
{"title":"Catalytic Enantioselective C–C Coupling of Alcohols for Polyketide Total Synthesis beyond Chiral Auxiliaries and Premetalated Reagents","authors":"Jessica Wu, Katherine L. Verboom, Michael J. Krische","doi":"10.1021/acs.chemrev.4c00858","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00858","url":null,"abstract":"Catalytic enantioselective hydrogen autotransfer reactions for the direct conversion of lower alcohols to higher alcohols are catalogued and their application to the total synthesis of polyketide natural products is described. These methods exploit a redox process in which alcohol oxidation is balanced by reductive generation of organometallic nucleophiles from unsaturated hydrocarbon pronucleophiles. Unlike classical carbonyl additions, premetalated reagents, chiral auxiliaries and discrete alcohol-to-aldehyde redox reactions are not required. Additionally, chemoselective dehydrogenation of primary alcohols in the presence of secondary alcohols enables C–C coupling in the absence of protecting groups.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"8 1","pages":""},"PeriodicalIF":62.1,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142788780","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-12-06DOI: 10.1021/acs.chemrev.4c0085810.1021/acs.chemrev.4c00858
Jessica Wu, Katherine L. Verboom and Michael J. Krische*,
{"title":"Catalytic Enantioselective C–C Coupling of Alcohols for Polyketide Total Synthesis beyond Chiral Auxiliaries and Premetalated Reagents","authors":"Jessica Wu, Katherine L. Verboom and Michael J. Krische*, ","doi":"10.1021/acs.chemrev.4c0085810.1021/acs.chemrev.4c00858","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00858https://doi.org/10.1021/acs.chemrev.4c00858","url":null,"abstract":"<p >Catalytic enantioselective hydrogen autotransfer reactions for the direct conversion of lower alcohols to higher alcohols are catalogued and their application to the total synthesis of polyketide natural products is described. These methods exploit a redox process in which alcohol oxidation is balanced by reductive generation of organometallic nucleophiles from unsaturated hydrocarbon pronucleophiles. Unlike classical carbonyl additions, premetalated reagents, chiral auxiliaries and discrete alcohol-to-aldehyde redox reactions are not required. Additionally, chemoselective dehydrogenation of primary alcohols in the presence of secondary alcohols enables C–C coupling in the absence of protecting groups.</p>","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"124 24","pages":"13715–13735 13715–13735"},"PeriodicalIF":51.4,"publicationDate":"2024-12-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143126188","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-12-02DOI: 10.1021/acs.chemrev.4c00251
Krishanu Ghosal, Swarup Krishna Bhattacharyya, Vivek Mishra, Han Zuilhof
{"title":"Click Chemistry for Biofunctional Polymers: From Observing to Steering Cell Behavior","authors":"Krishanu Ghosal, Swarup Krishna Bhattacharyya, Vivek Mishra, Han Zuilhof","doi":"10.1021/acs.chemrev.4c00251","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00251","url":null,"abstract":"Click chemistry has become one of the most powerful construction tools in the field of organic chemistry, materials science, and polymer science, as it offers hassle-free platforms for the high-yielding synthesis of novel materials and easy functionalization strategies. The absence of harsh reaction conditions or complicated workup procedures allowed the rapid development of novel biofunctional polymeric materials, such as biopolymers, tailor-made polymer surfaces, stimulus-responsive polymers, etc. In this review, we discuss various types of click reactions─including azide–alkyne cycloadditions, nucleophilic and radical thiol click reactions, a range of cycloadditions (Diels–Alder, tetrazole, nitrile oxide, etc.), sulfur fluoride exchange (SuFEx) click reaction, and oxime-hydrazone click reactions─and their use for the formation and study of biofunctional polymers. Following that, we discuss state-of-the-art biological applications of “click”-biofunctionalized polymers, including both passive applications (e.g., biosensing and bioimaging) and “active” ones that aim to direct changes in biosystems, e.g., for drug delivery, antiviral action, and tissue engineering. In conclusion, we have outlined future directions and existing challenges of click-based polymers for medicinal chemistry and clinical applications.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"13 1","pages":""},"PeriodicalIF":62.1,"publicationDate":"2024-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142760237","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-12-02DOI: 10.1021/acs.chemrev.4c00327
Chen Yang, Yilin Guo, Heng Zhang, Xuefeng Guo
{"title":"Utilization of Electric Fields to Modulate Molecular Activities on the Nanoscale: From Physical Properties to Chemical Reactions","authors":"Chen Yang, Yilin Guo, Heng Zhang, Xuefeng Guo","doi":"10.1021/acs.chemrev.4c00327","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00327","url":null,"abstract":"As a primary energy source, electricity drives broad fields from everyday electronic circuits to industrial chemical catalysis. From a chemistry viewpoint, studying electric field effects on chemical reactivity is highly important for revealing the intrinsic mechanisms of molecular behaviors and mastering chemical reactions. Recently, manipulating the molecular activity using electric fields has emerged as a new research field. In addition, because integration of molecules into electronic devices has the natural complementary metal-oxide-semiconductor compatibility, electric field-driven molecular devices meet the requirements for both electronic device miniaturization and precise regulation of chemical reactions. This Review provides a timely and comprehensive overview of recent state-of-the-art advances, including theoretical models and prototype devices for electric field-based manipulation of molecular activities. First, we summarize the main approaches to providing electric fields for molecules. Then, we introduce several methods to measure their strengths in different systems quantitatively. Subsequently, we provide detailed discussions of electric field-regulated photophysics, electron transport, molecular movements, and chemical reactions. This review intends to provide a technical manual for precise molecular control in devices via electric fields. This could lead to development of new optoelectronic functions, more efficient logic processing units, more precise bond-selective control, new catalytic paradigms, and new chemical reactions.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"37 1","pages":""},"PeriodicalIF":62.1,"publicationDate":"2024-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142760033","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-12-02DOI: 10.1021/acs.chemrev.4c0032710.1021/acs.chemrev.4c00327
Chen Yang, Yilin Guo, Heng Zhang and Xuefeng Guo*,
{"title":"Utilization of Electric Fields to Modulate Molecular Activities on the Nanoscale: From Physical Properties to Chemical Reactions","authors":"Chen Yang, Yilin Guo, Heng Zhang and Xuefeng Guo*, ","doi":"10.1021/acs.chemrev.4c0032710.1021/acs.chemrev.4c00327","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00327https://doi.org/10.1021/acs.chemrev.4c00327","url":null,"abstract":"<p >As a primary energy source, electricity drives broad fields from everyday electronic circuits to industrial chemical catalysis. From a chemistry viewpoint, studying electric field effects on chemical reactivity is highly important for revealing the intrinsic mechanisms of molecular behaviors and mastering chemical reactions. Recently, manipulating the molecular activity using electric fields has emerged as a new research field. In addition, because integration of molecules into electronic devices has the natural complementary metal-oxide-semiconductor compatibility, electric field-driven molecular devices meet the requirements for both electronic device miniaturization and precise regulation of chemical reactions. This Review provides a timely and comprehensive overview of recent state-of-the-art advances, including theoretical models and prototype devices for electric field-based manipulation of molecular activities. First, we summarize the main approaches to providing electric fields for molecules. Then, we introduce several methods to measure their strengths in different systems quantitatively. Subsequently, we provide detailed discussions of electric field-regulated photophysics, electron transport, molecular movements, and chemical reactions. This review intends to provide a technical manual for precise molecular control in devices via electric fields. This could lead to development of new optoelectronic functions, more efficient logic processing units, more precise bond-selective control, new catalytic paradigms, and new chemical reactions.</p>","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"125 1","pages":"223–293 223–293"},"PeriodicalIF":51.4,"publicationDate":"2024-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143085143","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-12-02DOI: 10.1021/acs.chemrev.4c0025110.1021/acs.chemrev.4c00251
Krishanu Ghosal, Swarup Krishna Bhattacharyya, Vivek Mishra and Han Zuilhof,
{"title":"Click Chemistry for Biofunctional Polymers: From Observing to Steering Cell Behavior","authors":"Krishanu Ghosal, Swarup Krishna Bhattacharyya, Vivek Mishra and Han Zuilhof, ","doi":"10.1021/acs.chemrev.4c0025110.1021/acs.chemrev.4c00251","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00251https://doi.org/10.1021/acs.chemrev.4c00251","url":null,"abstract":"<p >Click chemistry has become one of the most powerful construction tools in the field of organic chemistry, materials science, and polymer science, as it offers hassle-free platforms for the high-yielding synthesis of novel materials and easy functionalization strategies. The absence of harsh reaction conditions or complicated workup procedures allowed the rapid development of novel biofunctional polymeric materials, such as biopolymers, tailor-made polymer surfaces, stimulus-responsive polymers, etc. In this review, we discuss various types of click reactions─including azide–alkyne cycloadditions, nucleophilic and radical thiol click reactions, a range of cycloadditions (Diels–Alder, tetrazole, nitrile oxide, etc.), sulfur fluoride exchange (SuFEx) click reaction, and oxime-hydrazone click reactions─and their use for the formation and study of biofunctional polymers. Following that, we discuss state-of-the-art biological applications of “click”-biofunctionalized polymers, including both passive applications (e.g., biosensing and bioimaging) and “active” ones that aim to direct changes in biosystems, e.g., for drug delivery, antiviral action, and tissue engineering. In conclusion, we have outlined future directions and existing challenges of click-based polymers for medicinal chemistry and clinical applications.</p>","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"124 23","pages":"13216–13300 13216–13300"},"PeriodicalIF":51.4,"publicationDate":"2024-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.chemrev.4c00251","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142842138","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-11-27Epub Date: 2024-11-14DOI: 10.1021/acs.chemrev.3c00955
Joo-Chan Kim, YouJin Kim, Suho Cho, Hee-Sung Park
{"title":"Noncanonical Amino Acid Incorporation in Animals and Animal Cells.","authors":"Joo-Chan Kim, YouJin Kim, Suho Cho, Hee-Sung Park","doi":"10.1021/acs.chemrev.3c00955","DOIUrl":"10.1021/acs.chemrev.3c00955","url":null,"abstract":"<p><p>Noncanonical amino acids (ncAAs) are synthetic building blocks that, when incorporated into proteins, confer novel functions and enable precise control over biological processes. These small yet powerful tools offer unprecedented opportunities to investigate and manipulate various complex life forms. In particular, ncAA incorporation technology has garnered significant attention in the study of animals and their constituent cells, which serve as invaluable model organisms for gaining insights into human physiology, genetics, and diseases. This review will provide a comprehensive discussion on the applications of ncAA incorporation technology in animals and animal cells, covering past achievements, current developments, and future perspectives.</p>","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":" ","pages":"12463-12497"},"PeriodicalIF":51.4,"publicationDate":"2024-11-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142612700","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-11-26DOI: 10.1021/acs.chemrev.4c00524
Lauren E. Ehehalt, Omar M. Beleh, Isabella C. Priest, Julianna M. Mouat, Alyssa K. Olszewski, Benjamin N. Ahern, Alexandro R. Cruz, Benjamin K. Chi, Anthony J. Castro, Kai Kang, Jiang Wang, Daniel J. Weix
{"title":"Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis","authors":"Lauren E. Ehehalt, Omar M. Beleh, Isabella C. Priest, Julianna M. Mouat, Alyssa K. Olszewski, Benjamin N. Ahern, Alexandro R. Cruz, Benjamin K. Chi, Anthony J. Castro, Kai Kang, Jiang Wang, Daniel J. Weix","doi":"10.1021/acs.chemrev.4c00524","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00524","url":null,"abstract":"Cross-electrophile coupling (XEC), defined by us as the cross-coupling of two different σ-electrophiles that is driven by catalyst reduction, has seen rapid progression in recent years. As such, this review aims to summarize the field from its beginnings up until mid-2023 and to provide comprehensive coverage on synthetic methods and current state of mechanistic understanding. Chapters are split by type of bond formed, which include C(sp<sup>3</sup>)–C(sp<sup>3</sup>), C(sp<sup>2</sup>)–C(sp<sup>2</sup>), C(sp<sup>2</sup>)–C(sp<sup>3</sup>), and C(sp<sup>2</sup>)–C(sp) bond formation. Additional chapters include alkene difunctionalization, alkyne difunctionalization, and formation of carbon-heteroatom bonds. Each chapter is generally organized with an initial summary of mechanisms followed by detailed figures and notes on methodological developments and ending with application notes in synthesis. While XEC is becoming an increasingly utilized approach in synthesis, its early stage of development means that optimal catalysts, ligands, additives, and reductants are still in flux. This review has collected data on these and various other aspects of the reactions to capture the state of the field. Finally, the data collected on the papers in this review is offered as Supporting Information for readers.","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"258 1","pages":""},"PeriodicalIF":62.1,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142719064","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chemical ReviewsPub Date : 2024-11-26DOI: 10.1021/acs.chemrev.4c0052410.1021/acs.chemrev.4c00524
Lauren E. Ehehalt, Omar M. Beleh, Isabella C. Priest, Julianna M. Mouat, Alyssa K. Olszewski, Benjamin N. Ahern, Alexandro R. Cruz, Benjamin K. Chi, Anthony J. Castro, Kai Kang, Jiang Wang and Daniel J. Weix*,
{"title":"Cross-Electrophile Coupling: Principles, Methods, and Applications in Synthesis","authors":"Lauren E. Ehehalt, Omar M. Beleh, Isabella C. Priest, Julianna M. Mouat, Alyssa K. Olszewski, Benjamin N. Ahern, Alexandro R. Cruz, Benjamin K. Chi, Anthony J. Castro, Kai Kang, Jiang Wang and Daniel J. Weix*, ","doi":"10.1021/acs.chemrev.4c0052410.1021/acs.chemrev.4c00524","DOIUrl":"https://doi.org/10.1021/acs.chemrev.4c00524https://doi.org/10.1021/acs.chemrev.4c00524","url":null,"abstract":"<p >Cross-electrophile coupling (XEC), defined by us as the cross-coupling of two different σ-electrophiles that is driven by catalyst reduction, has seen rapid progression in recent years. As such, this review aims to summarize the field from its beginnings up until mid-2023 and to provide comprehensive coverage on synthetic methods and current state of mechanistic understanding. Chapters are split by type of bond formed, which include C(sp<sup>3</sup>)–C(sp<sup>3</sup>), C(sp<sup>2</sup>)–C(sp<sup>2</sup>), C(sp<sup>2</sup>)–C(sp<sup>3</sup>), and C(sp<sup>2</sup>)–C(sp) bond formation. Additional chapters include alkene difunctionalization, alkyne difunctionalization, and formation of carbon-heteroatom bonds. Each chapter is generally organized with an initial summary of mechanisms followed by detailed figures and notes on methodological developments and ending with application notes in synthesis. While XEC is becoming an increasingly utilized approach in synthesis, its early stage of development means that optimal catalysts, ligands, additives, and reductants are still in flux. This review has collected data on these and various other aspects of the reactions to capture the state of the field. Finally, the data collected on the papers in this review is offered as Supporting Information for readers.</p>","PeriodicalId":32,"journal":{"name":"Chemical Reviews","volume":"124 23","pages":"13397–13569 13397–13569"},"PeriodicalIF":51.4,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.chemrev.4c00524","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142850709","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}