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Cover Feature: Applying Metallo-Organic Ligand Design Principles to the Stereoselective Synthesis of a Peptide-Based Pd2L4X4 Cage (ChemistryEurope 1/2025)
ChemistryEurope Pub Date : 2025-01-12 DOI: 10.1002/ceur.202580102
Dr. Dominic F. Brightwell, Dr. Kushal Samanta, Dr. Jimmy Muldoon, Dr. Patricia C. Fleming, Dr. Yannick Ortin, Dr. Lina Mardiana, Dr. Paul G. Waddell, Dr. Michael J. Hall, Dr. Ewan R. Clark, Dr. Felipe Fantuzzi, Dr. Aniello Palma
{"title":"Cover Feature: Applying Metallo-Organic Ligand Design Principles to the Stereoselective Synthesis of a Peptide-Based Pd2L4X4 Cage (ChemistryEurope 1/2025)","authors":"Dr. Dominic F. Brightwell,&nbsp;Dr. Kushal Samanta,&nbsp;Dr. Jimmy Muldoon,&nbsp;Dr. Patricia C. Fleming,&nbsp;Dr. Yannick Ortin,&nbsp;Dr. Lina Mardiana,&nbsp;Dr. Paul G. Waddell,&nbsp;Dr. Michael J. Hall,&nbsp;Dr. Ewan R. Clark,&nbsp;Dr. Felipe Fantuzzi,&nbsp;Dr. Aniello Palma","doi":"10.1002/ceur.202580102","DOIUrl":"https://doi.org/10.1002/ceur.202580102","url":null,"abstract":"<p><b>The Cover Feature</b> celebrates the stereoselective synthesis of a peptide-based palladium cage. The chiral, low-symmetry peptide-based ligand used to generate this Pd cage could theoretically yield up to four structural isomers. Remarkably, only a single isomeric cage is formed in solution, the thermodynamically stable one. The image represents the single isomer emerging into the spotlight from all the possible isomers, shown in different colours in the background. More information can be found in the Research Article by A. Palma and co-workers (DOI: 10.1002/ceur.202400050).\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2025-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202580102","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143114459","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
Front Cover: (Ph3P)4C4P4: Effect of substitution on the Oligomerization of carbon phosphide radicals (ChemistryEurope 1/2025)
ChemistryEurope Pub Date : 2025-01-12 DOI: 10.1002/ceur.202580101
Dr. Moritz Scharnhölz, Dr. Jose Juan Gamboa Carballo, Dr. Nils Trapp, Dr. Rene Verel, Dr. Peter Coburger, Prof. Dr. Hansjörg Grützmacher
{"title":"Front Cover: (Ph3P)4C4P4: Effect of substitution on the Oligomerization of carbon phosphide radicals (ChemistryEurope 1/2025)","authors":"Dr. Moritz Scharnhölz,&nbsp;Dr. Jose Juan Gamboa Carballo,&nbsp;Dr. Nils Trapp,&nbsp;Dr. Rene Verel,&nbsp;Dr. Peter Coburger,&nbsp;Prof. Dr. Hansjörg Grützmacher","doi":"10.1002/ceur.202580101","DOIUrl":"https://doi.org/10.1002/ceur.202580101","url":null,"abstract":"<p><b>The Front Cover</b> shows the compound (PPh<sub>3</sub>)<sub>2</sub>(C<sub>2</sub>P<sub>2</sub>), depicted as a fictional, fast, and elusive creature adorned with PPh<sub>3</sub> antlers. This creature is theoretically characterized in the background illustration. However, as it exists only as a “fleeting intermediate”, previous attempts to capture its image resulted in only a blurred photograph taken with a wildlife camera. To increase the likelihood of obtaining a clearer image, the creature was enticed with its preferred food: iron carbonyls. This approach proved effective, leading to a successful clear photograph. Additionally, it was noted that when the creature is accompanied by a conspecific, it becomes less vigilant, allowing the image of a dimer to be captured. More information can be found in the Research Article by P. Coburger, H. Grützmacher and co-workers (DOI: 10.1002/ceur.202400061).\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2025-01-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202580101","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143114458","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
Amido-Triazole Complexes, “Normal” Triazole-Based Imines and Metallo-Mesoionic Imines
ChemistryEurope Pub Date : 2024-11-21 DOI: 10.1002/ceur.202400066
M. Sc. Richard Rudolf, Prof. Dr. Biprajit Sarkar
{"title":"Amido-Triazole Complexes, “Normal” Triazole-Based Imines and Metallo-Mesoionic Imines","authors":"M. Sc. Richard Rudolf,&nbsp;Prof. Dr. Biprajit Sarkar","doi":"10.1002/ceur.202400066","DOIUrl":"https://doi.org/10.1002/ceur.202400066","url":null,"abstract":"<p>Mesoionic compounds are hugely popular in fields such as organic chemistry, organometallic chemistry and homogeneous catalysis. A new sub-class are the mesoionic imines (MIIs). We present here 5-amino-4-pyridyl-1,2,3-triazole as a new and versatile synthon for generating first examples of metallo-MIIs. In this approach, we make use of metallation at the N-pyridyl/N3-triazole chelating pocket (instead of quarternisation of N3-triazole) and subsequent deprotonation to generate highly versatile and tunable metallo-MIIs. These unprecedented metallo-MIIs contain a highly nucleophilic N-donor site, and a tunable electrophilic metal site. Apart from displaying strong and directed H-bonding interactions like their “classical” MII analogues, the metallo-MIIs engage in aromatic C−F activation as well as meta−C−H activation reactions. Facile synthesis of homo and heterodincuelar complexes which contain a mixed coordinative saturation/unsaturation with these metallo-MIIs is presented. Apart from the metallo-MIIs we have also used 5-amino-4-pyridyl-1,2,3-triazole as a precursor to generate the first examples of amido-1,2,3-triazole complexes and the first example of a “normal” (and not mesoionic) 1,2,3-triazole based imine. Our results establish metallo-MIIs as a versatile new class of mesoionic compounds that combine the modularity of click reactions, with the functionality of metal fragments to generate electronically ambivalent compounds with a huge potential in synthetic chemistry, catalysis and beyond.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202400066","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143117524","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
Mechanochemical Halogenations and Rearrangement of Sydnones: Insight into Reaction Conditions and Mechanism
ChemistryEurope Pub Date : 2024-11-16 DOI: 10.1002/ceur.202400054
Dr. Florian Luttringer, Dr. Nicolas Pétry, Dr. Eric Clot, Prof. Dr. Xavier Bantreil, Dr. Frédéric Lamaty
{"title":"Mechanochemical Halogenations and Rearrangement of Sydnones: Insight into Reaction Conditions and Mechanism","authors":"Dr. Florian Luttringer,&nbsp;Dr. Nicolas Pétry,&nbsp;Dr. Eric Clot,&nbsp;Prof. Dr. Xavier Bantreil,&nbsp;Dr. Frédéric Lamaty","doi":"10.1002/ceur.202400054","DOIUrl":"https://doi.org/10.1002/ceur.202400054","url":null,"abstract":"<p>New mechanochemical methods for sydnone halogenation and insights into an efficient ring rearrangement yielding 1,3,4-oxadiazolin-2-ones by heated ball-milling are reported herein. Using equimolar amounts of <i>N</i>-chlorosuccinimide (NCS), oxone and sodium chloride, 3-phenylsydnone was quantitatively chlorinated in short reaction time and high yields. Moreover, an efficient method for the bromination of sydnones was developed by mixing equimolar amount of <i>N</i>-bromosuccinimide (NBS), Ac<sub>2</sub>O and a sydnone in a vibratory ball-mill, in the absence of solvent, with excellent yields and a reduced environmental impact. When the reaction was heated while milling, a fast and efficient ring rearrangement into 1,3,4-oxadiazolin-2-ones was observed. Insights concerning the mechanism of the reaction under solvent-less conditions, supported by DFT calculations, are discussed. The scope of this reaction, including solid anhydrides, is presented.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202400054","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143115871","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
Competitive Heavy-Atom Tunneling Reactions Controlled Through Electronic Effects
ChemistryEurope Pub Date : 2024-11-13 DOI: 10.1002/ceur.202400060
José P. L. Roque, Cláudio M. Nunes, Fumito Saito, Bastian Bernhardt, Rui Fausto, Peter R. Schreiner
{"title":"Competitive Heavy-Atom Tunneling Reactions Controlled Through Electronic Effects","authors":"José P. L. Roque,&nbsp;Cláudio M. Nunes,&nbsp;Fumito Saito,&nbsp;Bastian Bernhardt,&nbsp;Rui Fausto,&nbsp;Peter R. Schreiner","doi":"10.1002/ceur.202400060","DOIUrl":"https://doi.org/10.1002/ceur.202400060","url":null,"abstract":"<p>Controlling QMT reactivity remains exceptionally challenging and largely unexplored, as it requires rationales distinctly different from those used for classical chemical reactivity. Herein, we investigated how QMT reactivity can be controlled using electronic substituent effects. Benzazirines, which have the exceptional feature to react via two competitive QMT pathways, were used as model compounds. Three novel derivatives with increasingly stronger electron-donating substituents at C4 [R = OH, N(CH<sub>3</sub>)<sub>2</sub>, and N(CH<sub>2</sub>)<sub>4</sub>] were generated in argon matrices at 3 K. Remarkably, different QMT selectivities were observed in all benzazirines. As the electron-donating strength of the substituent increases, the QMT ring-opening to nitrene starts to compete with the QMT ring-expansion to ketenimine, becoming the dominant process for the strongest electron-donating substituent [N(CH<sub>2</sub>)<sub>4</sub>]. A theoretical analysis of the substituent effects on the QMT reactivity of benzazirines was performed and compared with the experimental data for these and other C4 derivatives. Overall, the results compellingly demonstrate how subtle changes in electronic effects can be used to fine-tune QMT selectivity.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202400060","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143114928","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
Applying Metallo-Organic Ligand Design Principles to the Stereoselective Synthesis of a Peptide-Based Pd2L4X4 Cage
ChemistryEurope Pub Date : 2024-11-13 DOI: 10.1002/ceur.202400050
Dr. Dominic F. Brightwell, Dr. Kushal Samanta, Dr. Jimmy Muldoon, Dr. Patricia C. Fleming, Dr. Yannick Ortin, Dr. Lina Mardiana, Dr. Paul G. Waddell, Dr. Michael J. Hall, Dr. Ewan R. Clark, Dr. Felipe Fantuzzi, Dr. Aniello Palma
{"title":"Applying Metallo-Organic Ligand Design Principles to the Stereoselective Synthesis of a Peptide-Based Pd2L4X4 Cage","authors":"Dr. Dominic F. Brightwell,&nbsp;Dr. Kushal Samanta,&nbsp;Dr. Jimmy Muldoon,&nbsp;Dr. Patricia C. Fleming,&nbsp;Dr. Yannick Ortin,&nbsp;Dr. Lina Mardiana,&nbsp;Dr. Paul G. Waddell,&nbsp;Dr. Michael J. Hall,&nbsp;Dr. Ewan R. Clark,&nbsp;Dr. Felipe Fantuzzi,&nbsp;Dr. Aniello Palma","doi":"10.1002/ceur.202400050","DOIUrl":"https://doi.org/10.1002/ceur.202400050","url":null,"abstract":"<p>The rational and controlled synthesis of metallo-organic cages using polyaromatic ligands is well established in the literature. There is a strong interest to advance this field towards the use of chiral ligands capable of yielding cages in a stereoselective manner. Herein, we demonstrate that the classical approach for designing metallo-organic cages can be translated to polyproline peptides, a biocompatible class of chiral ligands. We have successfully designed a series of polyprolines, which mimic the topology of ditopic polyaromatic ligands, to achieve the stereoselective synthesis of a novel Pd lantern cage. This cage exhibits excellent stability in water and demonstrates the stabilization of a highly reactive species in solution. This work will pave the way towards the stereospecific synthesis of more complex, functionalized peptide-based metallo-cages.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202400050","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143114929","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
Front Cover: Luminescence and Single-Molecule Magnet Properties in Ideal Symmetry Compounds: Example of a Near-Planar Tricoordinate Ytterbium(III) Amide (ChemistryEurope 6/2024) 封面：理想对称化合物的发光和单分子磁特性：近平面三配位镱(III)酰胺的实例（欧洲化学 6/2024）
ChemistryEurope Pub Date : 2024-11-12 DOI: 10.1002/ceur.202480601
Dr. Nimisha Jain, Dr. Félix Houard, Rémi Marchal, Marie Cordier, Dr. Boris Le Guennic, Dr. Yan Suffren, Dr. Yann Sarazin, Prof. Kevin Bernot
{"title":"Front Cover: Luminescence and Single-Molecule Magnet Properties in Ideal Symmetry Compounds: Example of a Near-Planar Tricoordinate Ytterbium(III) Amide (ChemistryEurope 6/2024)","authors":"Dr. Nimisha Jain,&nbsp;Dr. Félix Houard,&nbsp;Rémi Marchal,&nbsp;Marie Cordier,&nbsp;Dr. Boris Le Guennic,&nbsp;Dr. Yan Suffren,&nbsp;Dr. Yann Sarazin,&nbsp;Prof. Kevin Bernot","doi":"10.1002/ceur.202480601","DOIUrl":"https://doi.org/10.1002/ceur.202480601","url":null,"abstract":"<p><b>The Front Cover</b> shows a magnetic molecule that is being considered for nanoscale information storage and quantum applications. An ideal molecule based on a tri-coordinated Yb<sup>III</sup> was theorised in 2021. In their Research Article (DOI: 10.1002/ceur.202400062), Y. Sarazin, K. Bernot and co-workers show that this molecule does indeed possess the ideal electronic structure postulated, but that its performance is much weaker than expected. The anomalies observed in its infrared emission could be an experimental signature of active vibronic contributions in the molecule, detrimental to its magnetic behaviour.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"2 6","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202480601","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142664779","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/S cooperativity: from stoichiometric activation of Si−H bonds to catalytic hydrosilylation
ChemistryEurope Pub Date : 2024-11-12 DOI: 10.1002/ceur.202400079
Arnaud Clerc, Marceline Humbert, Sonia Mallet-Ladeira, Dr. Karinne Miqueu, Dr. Julien Monot, Prof. Blanca Martín-Vaca, Dr. Didier Bourissou
{"title":"Pd/S cooperativity: from stoichiometric activation of Si−H bonds to catalytic hydrosilylation","authors":"Arnaud Clerc,&nbsp;Marceline Humbert,&nbsp;Sonia Mallet-Ladeira,&nbsp;Dr. Karinne Miqueu,&nbsp;Dr. Julien Monot,&nbsp;Prof. Blanca Martín-Vaca,&nbsp;Dr. Didier Bourissou","doi":"10.1002/ceur.202400079","DOIUrl":"https://doi.org/10.1002/ceur.202400079","url":null,"abstract":"<p>With the aim to explore metal-ligand cooperation across Pd−S linkages, we designed a quinoline-based PNS tridentate ligand and prepared Pd(II) complexes thereof. Optimal solubility and stability of the dicationic complex [(PNS)Pd(II)]<sub>2</sub><sup>2+</sup> <b>IV<sub>2</sub></b> were achieved with B(C<sub>6</sub>F<sub>5</sub>)<sub>4</sub><sup>–</sup> as counter-anion. It adopts a thiolate-bridged dimeric structure with a (PdS)<sub>2</sub> core, but readily activates hydrosilanes across the Pd−S linkage. The resulting mononuclear Pd(II) hydride [(PNS<sup>SiR3</sup>)Pd(II)H]<sup>+</sup> <b>VI</b> was characterized by multi-nuclear NMR spectroscopy and the Si−H bond coordination/activation was studied computationally. Complex <b>IV<sub>2</sub></b> was found to efficiently catalyze the hydrosilylation of alkynes, internal as well as terminal, with good stereo and regioselectivity.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202400079","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143114501","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
Cover Feature: Water Chemistry at the Nanoscale: Clues for Resolving the “Water Paradox” Underlying the Emergence of Life (ChemistryEurope 6/2024) 封面专题：纳米尺度的水化学：解决生命出现背后的 "水悖论 "的线索（欧洲化学展 6/2024）
ChemistryEurope Pub Date : 2024-11-12 DOI: 10.1002/ceur.202480602
Dr. Hye-Eun Lee, Dr. Michael Russell, Prof. Ryuhei Nakamura
{"title":"Cover Feature: Water Chemistry at the Nanoscale: Clues for Resolving the “Water Paradox” Underlying the Emergence of Life (ChemistryEurope 6/2024)","authors":"Dr. Hye-Eun Lee,&nbsp;Dr. Michael Russell,&nbsp;Prof. Ryuhei Nakamura","doi":"10.1002/ceur.202480602","DOIUrl":"https://doi.org/10.1002/ceur.202480602","url":null,"abstract":"<p><b>The Cover Feature</b> illustrates the unique properties of nanoconfined water that can facilitate condensation reactions, potentially leading to the formation of biopolymers in submarine hydrothermal vents. In confined nanospace, the arrangement of water molecules changes significantly, lowering the dielectric constant of water and modulating the enthalpy–entropy correlation of chemical reactions. Due to these altered properties, layered minerals with confined nanospace drive enzyme-like condensation reactions. In this Concept (DOI: 10.1002/ceur.202400038), H.-E. Lee, M. Russell and R. Nakamura explore these possibilities, offering a clue to resolving the “water paradox” in the origin of life and an innovative use of nanoconfined water as a greener solvent for polymerization chemistry.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"2 6","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202480602","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142664780","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
Developing an On-Resin Synthesis of α-Galactosylceramide-Peptide Conjugate Vaccines
ChemistryEurope Pub Date : 2024-11-07 DOI: 10.1002/ceur.202400059
Dr. Michael A. Meijlink, Dr. Susanna T. S. Chan, Kathryn J. Farrand, Sarah L. Draper, Dr. Oliva K. Burn, Jasmine M. Seifert-Simpson, Ngarangi C. Mason, Dr. Lisa M. Connor, Prof. Ian F. Hermans, Prof. Gavin F. Painter, Dr. Benjamin J. Compton
{"title":"Developing an On-Resin Synthesis of α-Galactosylceramide-Peptide Conjugate Vaccines","authors":"Dr. Michael A. Meijlink,&nbsp;Dr. Susanna T. S. Chan,&nbsp;Kathryn J. Farrand,&nbsp;Sarah L. Draper,&nbsp;Dr. Oliva K. Burn,&nbsp;Jasmine M. Seifert-Simpson,&nbsp;Ngarangi C. Mason,&nbsp;Dr. Lisa M. Connor,&nbsp;Prof. Ian F. Hermans,&nbsp;Prof. Gavin F. Painter,&nbsp;Dr. Benjamin J. Compton","doi":"10.1002/ceur.202400059","DOIUrl":"https://doi.org/10.1002/ceur.202400059","url":null,"abstract":"<p>The covalent attachment of peptide antigens to the NKT cell agonist, α-galactosylceramide (αGalCer), generates self-adjuvanting vaccines that prevent and/or eliminate disease in animal models of cancer and infectious disease. To date, the manufacture of these glycolipid-peptide (GLP) conjugate vaccines utilises an automated solid-phase process to produce the peptide followed by a manual ‘wet chemistry’ conjugation step. To expedite GLP vaccine manufacture, we sought to develop methodology that enables the attachment of resin-bound peptide antigen to αGalCer via an amide bond thereby avoiding the need to carry out a separate chemoselective conjugation step. To facilitate this approach, novel analogues of αGalCer incorporating an activated ester spaced by an acid-resistant, protease-sensitive linker from either the 6′′-position or the <i>N</i>-acyl lipid were synthesised. Reacting these with resin-bound peptide afforded the conjugate vaccines in good to excellent yields and purity. In vivo testing showed that vaccines incorporating peptide antigen attached via the galactosyl head group induced strong antigen specific CD8<sup>+</sup> T cell responses compared to those with antigen attached via the lipid tail and control vaccine manufactured in a stepwise manner.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2024-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202400059","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143112825","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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