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5. Electrochemically Generated Carbocations in Organic Synthesis.

Author

Hawkins, Bill C., Chalker, Justin M., Coote, Michelle L., and Bissember, Alex C.

Abstract

This Minireview examines a selection of case studies that showcase distinctive and enabling electrochemical approaches that have allowed for the generation and reaction of carbocation intermediates under mild conditions. Particular emphasis is placed on the progress that has been made in this area of organic synthesis and polymer chemistry over the past decade. [ABSTRACT FROM AUTHOR]

Published
2024
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8. Synthesis and Applications of Polymers Made by Inverse Vulcanization

Author

Chalker, Justin M., Worthington, Max J. H., Lundquist, Nicholas A., Esdaile, Louisa J., Olivucci, Massimo, Editor-in-Chief, Wong, Wai-Yeung, Editor-in-Chief, Bayley, Hagan, Series Editor, Hughes, Greg, Series Editor, Hunter, Christopher A., Series Editor, Hwang, Seong-Ju, Series Editor, Ishihara, Kazuaki, Series Editor, Kirchner, Barbara, Series Editor, Krische, Michael J., Series Editor, Larsen, Delmar, Series Editor, Lehn, Jean-Marie, Series Editor, Luque, Rafael, Series Editor, Siegel, Jay S., Series Editor, Thiem, Joachim, Series Editor, Venturi, Margherita, Series Editor, Wong, Chi-Huey, Series Editor, Wong, Henry N.C., Series Editor, Yam, Vivian Wing-Wah, Series Editor, Yan, Chunhua, Series Editor, You, Shu-Li, Series Editor, and Jiang, Xuefeng, editor

Published
2019
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9. Exploring Inverse Vulcanized Dicyclopentadiene As a Polymer Matrix for Carbon Fiber Composites.

Author

Wickramasingha, Y. Athulya, Stojcevski, Filip, Eyckens, Daniel J., Hayne, David J., Chalker, Justin M., and Henderson, Luke C.

Subjects
CARBON fibers, FIBROUS composites, CARBON composites, REPURPOSED materials, DICYCLOPENTADIENE, POLYMERIC composites
Abstract

Inverse vulcanization of waste or renewable dienes has generated materials with phenomenal properties across a spectrum of applications. Nevertheless, the use of these materials for structural applications remains a challenge. Here, the use of an inverse vulcanized cyclopentadiene polymer as a resin for carbon fiber reinforced composites is explored. The dynamic S─S bonds in the polymer matrix are used to repair composite specimens over 5 generations by heating the material to 140 °C. A range of composites are manufactured and evaluated for their flexural properties, using a range of fiber orientations. Finally, this polymer is used to reinforce a carbon fiber fabric composed entirely of reclaimed materials, constituting a composite entirely composed of waste materials and second life carbon fibers. [ABSTRACT FROM AUTHOR]

Published
2024
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12. Reaction engineering for protein modification : tools for chemistry and biology

Author

Chalker, Justin M. and Davis, Benjamin G.

Subjects
572, Glycobiology, Chemistry & allied sciences, Biomimetic synthesis, Catalysis, Chemical biology, Crystallography, Heterocyclic chemistry, Mass spectrometry, Organic chemistry, Organic synthesis, Organometallic Chemistry, Protein chemistry, Synthetic organic chemistry, Biochemistry, Protein Modification, Reaction Engineering, Enzyme, Histone, Aqueous Chemistry, Cross-Coupling, Palladium, Olefin Metathesis, Ruthenium, Dehydroalanine, Cysteine
Abstract

Chemical modification of proteins is critical for many areas of biochemistry and medicine. Several methods for site-selective protein modification are reported in this Thesis that are useful in accessing both natural and artificial protein architectures. Multiple, complementary methods for the conversion of cysteine to dehydroalanine are described. Dehydroalanine is used as a general precursor to several post-translational modifications and glycosylation, polyprenylation, phosphorylation, and lysine methylation and acetylation are all accessible. These modifications and their mimics were explored on multiple proteins, including histone proteins. Unnatural modifications were also explored. The first examples of olefin metathesis and Suzuki-Miyaura cross-coupling on protein substrates are reported. Allyl sulfides were discovered to be remarkably reactive substrates in olefin metathesis, allowing use of this reaction in water and on proteins. For Suzuki-Miyaura cross-coupling, a new catalyst is described that is fully compatible with proteins. Both olefin metathesis and cross-coupling allow the formation of carbon-carbon bonds on proteins. The prospects of these transformations in chemical biology are discussed. Finally, a novel strategy is reported for the installation of natural, unnatural, and post-translationally modified amino acid residues on proteins. This technology relies on addition of carbon radicals to dehydroalanine. This method of "chemical mutagenesis" is anticipated to complement standard genetic manipulation of protein structure.

Published
2011

14. Electrochemical Synthesis of Poly(trisulfides)

Author

Pople, Jasmine M. M., primary, Nicholls, Thomas P., additional, Pham, Le Nhan, additional, Bloch, Witold M., additional, Lisboa, Lynn S., additional, Perkins, Michael V., additional, Gibson, Christopher T., additional, Coote, Michelle L., additional, Jia, Zhongfan, additional, and Chalker, Justin M., additional

Published
2023
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15. Posttranslational mutagenesis: A chemical strategy for exploring protein side-chain diversity

Author

Wright, Tom H., Bower, Ben J., Chalker, Justin M., Bernardes, Gonçalo J. L., Wiewiora, Rafel, Ng, Wai-Lung, Raj, Ritu, Faulkner, Sarah, Vallée, M. Robert J., Phanumartwiwath, Anuchit, Coleman, Oliver D., Thézénas, Marie-Laëtitia, Khan, Maola, Galan, Sébastien R. G., Lercher, Lukas, Schombs, Matthew W., Gerstberger, Stefanie, Palm-Espling, Maria E., Baldwin, Andrew J., Kessler, Benedikt M., Claridge, Timothy D. W., Mohammed, Shabaz, and Davis, Benjamin G.

Published
2016

16. Electrochemical Synthesis of Gold‐N‐Heterocyclic Carbene Complexes.

Author

Nicholls, Thomas P., Jia, Zhongfan, and Chalker, Justin M.

Subjects
CARBENE synthesis, GOLD electrodes, CATALYST testing
Abstract

An electrochemical synthesis of gold(I)‐N‐heterocyclic carbene (Au‐NHC) complexes has been developed. The electrochemical methodology uses only imidazolium salts, gold metal electrodes, and electricity to produce these complexes with hydrogen gas as the only by‐product. This high‐yielding and operationally simple procedure has been used to produce eight mononuclear and three dinuclear Au‐NHC complexes. The electrochemical procedure facilitates a clean reaction with no by‐products. As such, Au‐NHC complexes can be directly transferred to catalytic reactions without work‐up or purification. The Au‐NHC complexes were produced on‐demand and tested as catalysts in a vinylcyclopropanation reaction. All mononuclear Au‐NHC complexes performed similarly to or better than the isolated complexes. [ABSTRACT FROM AUTHOR]

Published
2024
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26. Chemically induced repair, adhesion, and recycling of polymers made by inverse vulcanization† †Electronic supplementary information (ESI) available: Full experimental details, characterisation data and mechanistic discussion. See DOI: 10.1039/d0sc00855a

Author

Tonkin, Samuel J., Gibson, Christopher T., Campbell, Jonathan A., Lewis, David A., Karton, Amir, Hasell, Tom, and Chalker, Justin M.

Subjects
Chemistry
Abstract

Polymers made by inverse vulcanization can be assembled, repaired, and recycled at room temperature through nucleophile-catalyzed S–S metathesis., Inverse vulcanization is a copolymerization of elemental sulfur and alkenes that provides unique materials with high sulfur content (typically ≥50% sulfur by mass). These polymers contain a dynamic and reactive polysulfide network that creates many opportunities for processing, assembly, and repair that are not possible with traditional plastics, rubbers and thermosets. In this study, we demonstrate that two surfaces of these sulfur polymers can be chemically joined at room temperature through a phosphine or amine-catalyzed exchange of the S–S bonds in the polymer. When the nucleophile is pyridine or triethylamine, we show that S–S metathesis only occurs at room temperature for a sulfur rank > 2—an important discovery for the design of polymers made by inverse vulcanization. This mechanistic understanding of the S–S metathesis was further supported with small molecule crossover experiments in addition to computational studies. Applications of this chemistry in latent adhesives, additive manufacturing, polymer repair, and recycling are also presented.

Published
2020

29. Vortex fluidic induced mass transfer across immiscible phases

Author

Jellicoe, Matt, primary, Igder, Aghil, additional, Chuah, Clarence, additional, Jones, Darryl B., additional, Luo, Xuan, additional, Stubbs, Keith A., additional, Crawley, Emily M., additional, Pye, Scott J., additional, Joseph, Nikita, additional, Vimalananthan, Kasturi, additional, Gardner, Zoe, additional, Harvey, David P., additional, Chen, Xianjue, additional, Salvemini, Filomena, additional, He, Shan, additional, Zhang, Wei, additional, Chalker, Justin M., additional, Quinton, Jamie S., additional, Tang, Youhong, additional, and Raston, Colin L., additional

Published
2022
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36. Cover Feature: Insulating Composites Made from Sulfur, Canola Oil, and Wool (ChemSusChem 11/2021)

Author

Bu Najmah, Israa, primary, Lundquist, Nicholas A., additional, Stanfield, Melissa K., additional, Stojcevski, Filip, additional, Campbell, Jonathan A., additional, Esdaile, Louisa J., additional, Gibson, Christopher T., additional, Lewis, David A., additional, Henderson, Luke C., additional, Hasell, Tom, additional, and Chalker, Justin M., additional

Published
2021
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37. Insulating composites made from sulfur, canola oil, and wool

Author

Bu Najmah, Israa, Lundquist, Nicholas A, Stanfield, Melissa K, Stojcevski, Filip, Campbell, Jonathan A, Esdaile, Louisa J, Gibson, Christopher T, Lewis, David A, Henderson, Luke C, Hasell, Tom, Chalker, Justin M, Bu Najmah, Israa, Lundquist, Nicholas A, Stanfield, Melissa K, Stojcevski, Filip, Campbell, Jonathan A, Esdaile, Louisa J, Gibson, Christopher T, Lewis, David A, Henderson, Luke C, Hasell, Tom, and Chalker, Justin M

Published
2021

39. Norbornene Probes for the Detection of Cysteine Sulfenic Acid in Cells

Author

Alcock, Lisa J, Oliveira, Bruno L, Deery, Michael J, Pukala, Tara L, Perkins, Michael V, Bernardes, Gonçalo JL, Chalker, Justin M, Alcock, Lisa J [0000-0001-9068-0756], Pukala, Tara L [0000-0001-7391-1436], Bernardes, Gonçalo JL [0000-0001-6594-8917], Chalker, Justin M [0000-0002-7504-5508], and Apollo - University of Cambridge Repository

Subjects
Molecular Probes, Cysteine, Norbornanes, Oxidation-Reduction, Sulfenic Acids
Abstract

Norbornene derivatives were validated as probes for cysteine sulfenic acid on proteins and in live cells. Trapping sulfenic acids with norbornene probes is highly selective and revealed a different reactivity profile than the traditional dimedone reagent. The norbornene probe also revealed a superior chemoselectivity when compared to a commonly used dimedone probe. Together, these results advance the study of cysteine oxidation in biological systems.

Published
2019

42. Insulating Composites Made from Sulfur, Canola Oil, and Wool**

Author

Bu Najmah, Israa, primary, Lundquist, Nicholas A., additional, Stanfield, Melissa K., additional, Stojcevski, Filip, additional, Campbell, Jonathan A., additional, Esdaile, Louisa J., additional, Gibson, Christopher T., additional, Lewis, David A., additional, Henderson, Luke C., additional, Hasell, Tom, additional, and Chalker, Justin M., additional

Published
2021
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43. Reactive compression molding post-inverse vulcanization: a method to assemble, recycle, and repurpose sulfur polymers and composites

Author

Lundquist, Nicholas A., Tikoalu, Alfrets D., Worthington, Max J. H., Shapter, Ryan, Tonkin, Samuel J., Stojcevski, Filip, Mann, Maximilian, Gibson, Christopher T., Gascooke, Jason R., Karton, Amir, Henderson, Luke C., Esdaile, Louisa J., Chalker, Justin M., Lundquist, Nicholas A., Tikoalu, Alfrets D., Worthington, Max J. H., Shapter, Ryan, Tonkin, Samuel J., Stojcevski, Filip, Mann, Maximilian, Gibson, Christopher T., Gascooke, Jason R., Karton, Amir, Henderson, Luke C., Esdaile, Louisa J., and Chalker, Justin M.

Published
2020

44. Proteome-Wide Survey of Cysteine Oxidation by Using a Norbornene Probe

Author

Alcock, Lisa J, Langini, Maike, Stühler, Kai, Remke, Marc, Perkins, Michael V, Bernardes, Gonçalo JL, Chalker, Justin M, Lopes Bernardes, Goncalo [0000-0001-6594-8917], and Apollo - University of Cambridge Repository

Subjects
sulfenome, oxidative stress, norbornene, cysteine oxidation, sulfenic acid
Abstract

Rapid detection of cysteine oxidation in living cells is critical in advancing our understanding of responses to reactive oxygen species (ROS) and oxidative stress. Accordingly, there is a need to develop chemical probes that facilitate proteome-wide detection of cysteine's many oxidation states. Herein, we report the first whole-cell proteomics analysis using a norbornene probe to detect the initial product of cysteine oxidation: cysteine sulfenic acid. The oxidised proteins identified in the HeLa cell model represent the first targets of the ROS hydrogen peroxide. The panel of protein hits provides new and important information about the targets of oxidative stress, including 148 new protein members of the sulfenome. These findings provide new leads for the study and understanding of redox signalling and diseases associated with oxidative stress.

Published
2019

45. Carbonisation of a polymer made from sulfur and canola oil

Author

Mann, Maximilian, primary, Luo, Xuan, additional, Tikoalu, Alfrets D., additional, Gibson, Christopher T., additional, Yin, Yanting, additional, Al-Attabi, Riyadh, additional, Andersson, Gunther G., additional, Raston, Colin L., additional, Henderson, Luke C., additional, Pring, Allan, additional, Hasell, Tom, additional, and Chalker, Justin M., additional

Published
2021
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46. Sub-micron moulding topological mass transport regimes in angled vortex fluidic flow

Author

Alharbi, Thaar M. D., primary, Jellicoe, Matt, additional, Luo, Xuan, additional, Vimalanathan, Kasturi, additional, Alsulami, Ibrahim K., additional, AL Harbi, Bediea S., additional, Igder, Aghil, additional, Alrashaidi, Fayed A. J., additional, Chen, Xianjue, additional, Stubbs, Keith A., additional, Chalker, Justin M., additional, Zhang, Wei, additional, Boulos, Ramiz A., additional, Jones, Darryl B., additional, Quinton, Jamie S., additional, and Raston, Colin L., additional

Published
2021
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