All Outputs (53)

Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas (2024)
Journal Article
Hampton, A. S., Hodgson, D. R. W., McDougald, G., Wang, L., & Sandford, G. (2024). Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas. Beilstein Journal of Organic Chemistry, 20, 460-469. https://doi.org/10.3762/bjoc.20.41

Solutions of 1,3-diketones and 1,3-ketoester derivatives react with fluorine to give the corresponding 2,2-difluoro-1,3-dicarbonyl derivatives in the presence of quinuclidine. Quinuclidine reacts with fluorine in situ to generate a fluoride ion that... Read More about Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas.

Going Full Circle with Organocatalysis and Biocatalysis: The Latent Potential of Cofactor Mimics in Asymmetric Synthesis (2023)
Journal Article
Murray, J., Hodgson, D. R., & O’Donoghue, A. C. (2023). Going Full Circle with Organocatalysis and Biocatalysis: The Latent Potential of Cofactor Mimics in Asymmetric Synthesis. Journal of Organic Chemistry, https://doi.org/10.1021/acs.joc.2c02747

Many enzymes work in tandem with small molecule cofactors, which have inspired organocatalyst designs. Chemical modification of cofactor scaffolds has increased organocatalytic reactivity and reaction scope. This synopsis presents a selection of rece... Read More about Going Full Circle with Organocatalysis and Biocatalysis: The Latent Potential of Cofactor Mimics in Asymmetric Synthesis.

Allophycocyanin A is a carbon dioxide receptor in the cyanobacterial phycobilisome (2022)
Journal Article
Guillen-Garcia, A., Gibson, S., Jordan, C., Ramaswamy, V., Linthwaite, V., Bromley, E., …Cann, M. (2022). Allophycocyanin A is a carbon dioxide receptor in the cyanobacterial phycobilisome. Nature Communications, 13, Article 5289. https://doi.org/10.1038/s41467-022-32925-6

Light harvesting is fundamental for production of ATP and reducing equivalents for CO2 fixation during photosynthesis. However, electronic energy transfer (EET) through a photosystem can harm the photosynthetic apparatus when not balanced with CO2. H... Read More about Allophycocyanin A is a carbon dioxide receptor in the cyanobacterial phycobilisome.

Ubiquitin is a carbon dioxide-binding protein (2021)
Journal Article
Linthwaite, V., Pawloski, W., Pegg, H., Townsend, P., Thomas, M., Brown, A., …Cann, M. (2021). Ubiquitin is a carbon dioxide-binding protein. Science Advances, 7(39), Article eabi5507. https://doi.org/10.1126/sciadv.abi5507

The identification of CO2-binding proteins is crucial to understanding CO2-regulated molecular processes. CO2 can form a reversible posttranslational modification through carbamylation of neutral N-terminal -amino or lysine -amino groups. We have p... Read More about Ubiquitin is a carbon dioxide-binding protein.

Triazolium Salt Organocatalysis: Mechanistic Evaluation of Unusual Ortho-Substituent Effects on Deprotonation (2021)
Journal Article
Quinn, P., Smith, M. S., Zhu, J., Hodgson, D. R., & O’Donoghue, A. C. (2021). Triazolium Salt Organocatalysis: Mechanistic Evaluation of Unusual Ortho-Substituent Effects on Deprotonation. Catalysts, 11(9), Article 1055. https://doi.org/10.3390/catal11091055

Organocatalysis by N-heterocyclic carbenes is normally initiated by the deprotonation of precursor azolium ions to form active nucleophilic species. Substituent effects on deprotonation have an impact on catalytic efficiency and provide insight into... Read More about Triazolium Salt Organocatalysis: Mechanistic Evaluation of Unusual Ortho-Substituent Effects on Deprotonation.

Reactivities of electrophilic N–F fluorinating reagents (2020)
Journal Article
Rozatian, N., & Hodgson, D. R. (2021). Reactivities of electrophilic N–F fluorinating reagents. Chemical Communications, 57(6), 683-712. https://doi.org/10.1039/d0cc06339h

Electrophilic fluorination represents one of the most direct and useful methods available for the selective introduction of fluorine into organic compounds. Electrophilic fluorinating reagents of the N–F class have revolutionised the incorporation of... Read More about Reactivities of electrophilic N–F fluorinating reagents.

Kinetics of electrophilic fluorination of steroids and epimerisation of fluorosteroids (2020)
Journal Article
Rozatian, N., Harsanyi, A., Murray, B. J., Hampton, A. S., Chin, E. J., Cook, A. S., …Sandford, G. (2020). Kinetics of electrophilic fluorination of steroids and epimerisation of fluorosteroids. Chemistry - A European Journal, 26(52), 12027-12035. https://doi.org/10.1002/chem.202001120

Fluorinated steroids, which are synthesised by electrophilic fluorination, form a significant proportion of marketed pharmaceuticals. To gain quantitative information on fluorination at the 6‐position of steroids, we conducted kinetics studies on eno... Read More about Kinetics of electrophilic fluorination of steroids and epimerisation of fluorosteroids.

Stereoselective Syntheses of 3’-Hydroxyamino- and 3’-Methoxyamino-2’,3’-Dideoxynucleosides (2019)
Journal Article
Bose, S., & Hodgson, D. R. (2019). Stereoselective Syntheses of 3’-Hydroxyamino- and 3’-Methoxyamino-2’,3’-Dideoxynucleosides. Organic Letters, 21(22), 9084-9088. https://doi.org/10.1021/acs.orglett.9b03474

Aminonucleosides are used as key motifs in medicinal and bioconjugate chemistry; however, existing strategies toward 3′-hypernucleophilic amine systems do not readily deliver deoxyribo-configured products. We report diastereoselective syntheses of de... Read More about Stereoselective Syntheses of 3’-Hydroxyamino- and 3’-Methoxyamino-2’,3’-Dideoxynucleosides.

Enolization rates control mono- versus di-fluorination of 1,3-dicarbonyl derivatives (2019)
Journal Article
Rozatian, N., Beeby, A., Ashworth, I. W., Sandford, G., & Hodgson, D. R. (2019). Enolization rates control mono- versus di-fluorination of 1,3-dicarbonyl derivatives. Chemical Science, 10(44), 10318-10330. https://doi.org/10.1039/c9sc04185k

Fluorine-containing 1,3-dicarbonyl derivatives are essential building blocks for drug discovery and manufacture. To understand the factors that determine selectivity between mono- and di-fluorination of 1,3-dicarbonyls systems, we have performed kine... Read More about Enolization rates control mono- versus di-fluorination of 1,3-dicarbonyl derivatives.

TRIPHOSPHORYLATION REACTION (2019)
Patent
Hodgson, D. (2020). TRIPHOSPHORYLATION REACTION

The disclosure provides a method of producing a triphosphate compound. The method comprises (a) dissolving imidazole in an aqueous alkaline solution to make an imidazole solution; (b) dissolving phosphoryl halide in an organic solvent to make an orga... Read More about TRIPHOSPHORYLATION REACTION.

A Quantitative Reactivity Scale for Electrophilic Fluorinating Reagents (2018)
Journal Article
Rozatian, N., Ashworth, I. W., Sandford, G., & Hodgson, D. R. (2018). A Quantitative Reactivity Scale for Electrophilic Fluorinating Reagents. Chemical Science, 9(46), 8692-8702. https://doi.org/10.1039/c8sc03596b

Electrophilic N-F fluorination agents underpin the introduction of fluorine in aliphatic systems across drug and academic research. The choice of N-F reagent is currently determined through empirical experimentation in the absence of quantitative val... Read More about A Quantitative Reactivity Scale for Electrophilic Fluorinating Reagents.

The identification of carbon dioxide mediated protein post-translational modifications (2018)
Journal Article
Linthwaite, V., Janus, J., Brown, A., Wong-Pascua, D., O’Donoghue, A., Porter, A., …Cann, M. (2018). The identification of carbon dioxide mediated protein post-translational modifications. Nature Communications, 9, Article 3092. https://doi.org/10.1038/s41467-018-05475-z

Carbon dioxide is vital to the chemistry of life processes including metabolism, cellular homoeostasis, and pathogenesis. CO2 is generally unreactive but can combine with neutral amines to form carbamates on proteins under physiological conditions. T... Read More about The identification of carbon dioxide mediated protein post-translational modifications.

Physicochemical Aspects of Aqueous and Nonaqueous Approaches to the Preparation of Nucleosides, Nucleotides and Phosphate Ester Mimics (2017)
Book Chapter
Hodgson, D. R. (2017). Physicochemical Aspects of Aqueous and Nonaqueous Approaches to the Preparation of Nucleosides, Nucleotides and Phosphate Ester Mimics. In N. Williams, & I. Williams (Eds.), Advances in Physical Organic Chemistry. Elsevier. https://doi.org/10.1016/bs.apoc.2017.09.002

Synthetic approaches towards nucleosides, nucleotides and their mimics are reviewed in the context of the underpinning physicochemical properties of these classes of molecules and how these properties impinge upon the methods and reagents used to pre... Read More about Physicochemical Aspects of Aqueous and Nonaqueous Approaches to the Preparation of Nucleosides, Nucleotides and Phosphate Ester Mimics.

Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill (2017)
Journal Article
Eguaogie, O., Conlon, P. F., Ravalico, F., Sweet, J. S., Elder, T. B., Conway, L. P., …Vyle, J. S. (2017). Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill. Beilstein Journal of Organic Chemistry, 13, 87-92. https://doi.org/10.3762/bjoc.13.11

Vibration ball-milling in a zirconia-lined vessel afforded clean and quantitative nucleophilic displacement reactions between 4-methoxybenzylthiolate salts and nucleoside 5′-halides or 5′-tosylates in five to 60 minutes. Under these conditions, commo... Read More about Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill.

The Synthesis, Conformation and Hydrolytic Stability of an N,S-bridging Thiophosphoramidate Analogue of Thymidylyl-3ʹ,5ʹ-Thymidine (2016)
Journal Article
Conway, L., Mikkola, S., O’Donoghue, A., & Hodgson, D. (2016). The Synthesis, Conformation and Hydrolytic Stability of an N,S-bridging Thiophosphoramidate Analogue of Thymidylyl-3ʹ,5ʹ-Thymidine. Organic and Biomolecular Chemistry, 14(30), 7361-7367. https://doi.org/10.1039/c6ob01270a

A 3'-N,5'-S-bridging thiophosphoramidate analogue of thymidylyl-3ʹ,5ʹ-thymidine was synthesised under aqueous conditions. 1H NMR conformational measurements show that the 3'-N-substituted deoxyribose ring is biased towards the 'north', RNA-like confo... Read More about The Synthesis, Conformation and Hydrolytic Stability of an N,S-bridging Thiophosphoramidate Analogue of Thymidylyl-3ʹ,5ʹ-Thymidine.

Synthesis of novel pyrophosphorothiolate-linked dinucleoside cap analogues in a ball mill (2015)
Journal Article
Eguaogie, O., Cooke, L. A., Martin, P. M., Ravalico, F., Conway, L. P., Hodgson, D. R., …Vyle, J. S. (2016). Synthesis of novel pyrophosphorothiolate-linked dinucleoside cap analogues in a ball mill. Organic and Biomolecular Chemistry, 14(4), 1201-1205. https://doi.org/10.1039/c5ob02061a

Michaelis–Arbuzov reactions of S-aryl disulfide derivatives of 3′-thiothymidine or 5′-thioadenosine with tris(trimethylsilyl) phosphite proceeded in high yields to the corresponding phosphorothiolate monoesters. Subsequent hydrolytic desilylation and... Read More about Synthesis of novel pyrophosphorothiolate-linked dinucleoside cap analogues in a ball mill.

Metal–ion promoted cleavage of nucleoside diphosphosugars: A model for reactions of phosphodiester bonds in carbohydrates (2015)
Journal Article
Dano, M., Elmeranta, M., Hodgson, D. R., Jaakkola, J., Korhonen, H., & Mikkola, S. (2015). Metal–ion promoted cleavage of nucleoside diphosphosugars: A model for reactions of phosphodiester bonds in carbohydrates. JBIC Journal of Biological Inorganic Chemistry, 20(8), 1299-1306. https://doi.org/10.1007/s00775-015-1308-9

Cleavage of five different nucleoside diphosphosugars has been studied in the presence of Cu2+ and Zn2+ complexes. The results show that metal ion catalysts promote the cleavage via intramolecular transesterification whenever a neighbouring HO group... Read More about Metal–ion promoted cleavage of nucleoside diphosphosugars: A model for reactions of phosphodiester bonds in carbohydrates.

Preparation of an antibacterial poly(ionic liquid) graft copolymer of hydroxyethyl cellulose (2015)
Journal Article
Joubert, F., Yeo, R. P., Sharples, G. J., Musa, O. M., Hodgson, D. R., & Cameron, N. R. (2015). Preparation of an antibacterial poly(ionic liquid) graft copolymer of hydroxyethyl cellulose. Biomacromolecules, 16(12), 397-3979. https://doi.org/10.1021/acs.biomac.5b01300

Poly(ionic liquid)s (P(IL)s) of different degrees of polymerisation (10, 50 and 100) were prepared via RAFT polymerisation using an alkyne-terminated xanthate as transfer agent, with a monomer conversion of up to ~80% and a ƉM of 1.5 for P(IL)100. Su... Read More about Preparation of an antibacterial poly(ionic liquid) graft copolymer of hydroxyethyl cellulose.

The role of protein-ligand contacts in allosteric regulation of the Escherichia coli Catabolite Activator Protein (2015)
Journal Article
Townsend, P., Rodgers, T., Glover, L., Korhonen, H., Richards, S., Colwell, L., …Cann, M. (2015). The role of protein-ligand contacts in allosteric regulation of the Escherichia coli Catabolite Activator Protein. Journal of Biological Chemistry, 290(36), 22225-22235. https://doi.org/10.1074/jbc.m115.669267

Allostery is a fundamental process by which ligand binding to a protein alters its activity at a distant site. Both experimental and theoretical evidence demonstrate that allostery can be communicated through altered slow relaxation protein dynamics... Read More about The role of protein-ligand contacts in allosteric regulation of the Escherichia coli Catabolite Activator Protein.

Understanding Thio-Effects in Simple Phosphoryl Systems: Role of Solvent Effects and Nucleophile Charge (2015)
Journal Article
Carvalho, A., O’Donoghue, A., Hodgson, D., & Kamerlin, S. (2015). Understanding Thio-Effects in Simple Phosphoryl Systems: Role of Solvent Effects and Nucleophile Charge. Organic and Biomolecular Chemistry, 13(19), 5391-5398. https://doi.org/10.1039/c5ob00309a

Recent experimental work (J. Org. Chem., 2012, 77, 5829) demonstrated pronounced differences in measured thio-effects for the hydrolysis of (thio)phosphodichloridates by water and hydroxide nucleophiles. In the present work, we have performed detaile... Read More about Understanding Thio-Effects in Simple Phosphoryl Systems: Role of Solvent Effects and Nucleophile Charge.