Professor ROBERT STOCKMAN's Outputs (37)

A short stereodivergent synthesis of (R) and (S)-nicotine (2025)
Journal Article
Dawood, R. S., & Stockman, R. A. (2025). A short stereodivergent synthesis of (R) and (S)-nicotine. New Journal of Chemistry, 49(12), 4860-4863. https://doi.org/10.1039/D5NJ00366K

A straightforward and efficient enantioselective synthesis of (S)-nicotine and unnatural (R)-nicotine with high yields is presented. Judicious choice of solvent in the key asymmetric addition of the pyridyl Grignard reagent to the chiral sulfinimine... Read More about A short stereodivergent synthesis of (R) and (S)-nicotine.

Rapid, Highly Sustainable Ring-Opening Polymerization via Resonant Acoustic Mixing (2025)
Journal Article
Fowler, H. R., O’Shea, R., Sefton, J., Howard, S. C., Muir, B. W., Stockman, R. A., Taresco, V., & Irvine, D. J. (2025). Rapid, Highly Sustainable Ring-Opening Polymerization via Resonant Acoustic Mixing. ACS Sustainable Chemistry and Engineering, 13(5), 1916–1926. https://doi.org/10.1021/acssuschemeng.4c06330

Reported herein is the first combination of resonant acoustic mixing (RAM) and controlled ring-opening polymerization (ROP) to deliver fully sustainable, end-functionalized, biodegradable polymers via a manufacturing route with a much-reduced environ... Read More about Rapid, Highly Sustainable Ring-Opening Polymerization via Resonant Acoustic Mixing.

Sustainable, upscaled synthesis of pinene-derived (meth)acrylates and their application as high Tg monomers in styrene/acrylic-based bioderived copolymer coatings (2024)
Journal Article
Pin-Nó, M., Jacob, P. L., Taresco, V., Kastelijn, M., Nabuurs, T., Surti, C., Bilney, J., Daly, J., Keddie, D. J., Howdle, S. M., & Stockman, R. A. (2024). Sustainable, upscaled synthesis of pinene-derived (meth)acrylates and their application as high Tg monomers in styrene/acrylic-based bioderived copolymer coatings. RSC Sustainability, 2(9), 2515-2523. https://doi.org/10.1039/D4SU00210E

An improved synthesis of the pinene-derived monomers (3-pinanyl acrylate 1 and 3-pinanyl methacrylate 2), replacing hazardous and/or expensive reagents from established methods with cheaper, more innocuous and sustainable reagents, is reported; the m... Read More about Sustainable, upscaled synthesis of pinene-derived (meth)acrylates and their application as high Tg monomers in styrene/acrylic-based bioderived copolymer coatings.

Simultaneous geraniol and citronellol transesterification using Pseudomonas fluorescens lipase for the production of fragrance and flavour esters: a kinetic study (2024)
Journal Article
Wikaputri, A. S., Irvine, D. J., Stockman, R. A., & Shivaprasad, P. (2024). Simultaneous geraniol and citronellol transesterification using Pseudomonas fluorescens lipase for the production of fragrance and flavour esters: a kinetic study. Journal of Agriculture and Food Research, 16, Article 101186. https://doi.org/10.1016/j.jafr.2024.101186

This study aims to develop, for the very first time, a kinetic model for the simultaneous transesterification of geraniol and citronellol using Pseudomonas fluorescens lipase to produce their respective esters. This allows us to test the feasibility... Read More about Simultaneous geraniol and citronellol transesterification using Pseudomonas fluorescens lipase for the production of fragrance and flavour esters: a kinetic study.

Pea aphid odorant-binding protein ApisOBP6 discriminates between aphid sex pheromone components, aphid alarm pheromone and a host plant volatile (2023)
Journal Article
Sims, C., Birkett, M. A., Oldham, N. J., Stockman, R. A., & Withall, D. M. (2023). Pea aphid odorant-binding protein ApisOBP6 discriminates between aphid sex pheromone components, aphid alarm pheromone and a host plant volatile. Insect Biochemistry and Molecular Biology, 162, Article 104026. https://doi.org/10.1016/j.ibmb.2023.104026

Olfactory perception of pheromones in insects involves odorant-binding proteins (OBPs), relatively small proteins (ca.110-240 amino acid residues) that can bind reversibly to behaviourally active olfactory ligands. In this study, we investigated the... Read More about Pea aphid odorant-binding protein ApisOBP6 discriminates between aphid sex pheromone components, aphid alarm pheromone and a host plant volatile.

Evaluation of two terpene-derived polymers as consolidants for archaeological wood (2023)
Journal Article
Cutajar, M., Braovac, S., Stockman, R. A., Howdle, S. M., & Harding, S. E. (2023). Evaluation of two terpene-derived polymers as consolidants for archaeological wood. Scientific Reports, 13(1), Article 3664. https://doi.org/10.1038/s41598-023-29785-5

The evaluation of two terpene-derived polymers, termed TPA6 and TPA7, as possible consolidants for archaeological wood was carried out. The overall objective of this work was to expand the non-aqueous treatment toolkit which is available for the cons... Read More about Evaluation of two terpene-derived polymers as consolidants for archaeological wood.

Oxidation of Monoterpenes to Form Diols and Triols: A Versatile Toolbox for Polymer Synthesis (2023)
Journal Article
Fowler, H. R., O'Brien, D. M., Keddie, D. J., Alexander, C., Irvine, D. J., Stockman, R. A., Howdle, S. M., & Taresco, V. (2023). Oxidation of Monoterpenes to Form Diols and Triols: A Versatile Toolbox for Polymer Synthesis. Macromolecular Chemistry and Physics, 224(8), Article 2200446. https://doi.org/10.1002/macp.202200446

Polyols and polyacrylates have a wide range of applications in polymer synthesis as monomers, initiators, or building blocks in a variety of polymerization reaction types. With an ever-growing need to reduce the global dependency on fossil fuels, fin... Read More about Oxidation of Monoterpenes to Form Diols and Triols: A Versatile Toolbox for Polymer Synthesis.

Predictive Molecular Design and Structure–Property Validation of Novel Terpene-Based, Sustainably Sourced Bacterial Biofilm-Resistant Materials (2023)
Journal Article
Cuzzucoli Crucitti, V., Ilchev, A., Moore, J. C., Fowler, H. R., Dubern, J.-F., Sanni, O., Xue, X., Husband, B. K., Dundas, A. A., Smith, S., Wildman, J. L., Taresco, V., Williams, P., Alexander, M. R., Howdle, S. M., Wildman, R. D., Stockman, R. A., & Irvine, D. J. (2023). Predictive Molecular Design and Structure–Property Validation of Novel Terpene-Based, Sustainably Sourced Bacterial Biofilm-Resistant Materials. Biomacromolecules, https://doi.org/10.1021/acs.biomac.2c00721

Presented in this work is the use of a molecular descriptor, termed the α parameter, to aid in the design of a series of novel, terpene-based, and sustainable polymers that were resistant to biofilm formation by the model bacterial pathogen Pseudomon... Read More about Predictive Molecular Design and Structure–Property Validation of Novel Terpene-Based, Sustainably Sourced Bacterial Biofilm-Resistant Materials.

Comparative hydrodynamic characterisation of two hydroxylated polymers based on α-pinene- or oleic acid-derived monomers for potential use as archaeological consolidants (2022)
Journal Article
Cutajar, M., Machado, F., Cuzzucoli Crucitti, V., Braovac, S., Stockman, R. A., Howdle, S. M., & Harding, S. E. (2022). Comparative hydrodynamic characterisation of two hydroxylated polymers based on α-pinene- or oleic acid-derived monomers for potential use as archaeological consolidants. Scientific Reports, 12(1), Article 18411. https://doi.org/10.1038/s41598-022-21027-4

The Oseberg Viking ship burial is one of the most extensive collections of Viking wooden artefacts ever excavated in Norway. In the early twentieth century, many of these artefacts were treated with alum in order to preserve them, inadvertently leadi... Read More about Comparative hydrodynamic characterisation of two hydroxylated polymers based on α-pinene- or oleic acid-derived monomers for potential use as archaeological consolidants.

Sustainable ABA triblock methacrylate copolymers incorporating both high and low Tg terpene-derived monomers (2022)
Journal Article
Atkinson, R. L., Elsmore, M., Smith, S., Reynolds-Green, M., Topham, P. D., Toolan, D. T., Derry, M. J., Monaghan, O., Taresco, V., Irvine, D. J., Stockman, R. A., De Focatiis, D. S., & Howdle, S. M. (2022). Sustainable ABA triblock methacrylate copolymers incorporating both high and low Tg terpene-derived monomers. European Polymer Journal, 179, Article 11567. https://doi.org/10.1016/j.eurpolymj.2022.111567

We report the synthesis of novel terpene-based monomers: nopinyl acrylate and methacrylate, from naturally abundant β-pinene. A very high Tg value was observed for poly(nopinyl methacrylate) when synthesised by free radical polymerisation, and well-d... Read More about Sustainable ABA triblock methacrylate copolymers incorporating both high and low Tg terpene-derived monomers.

A self-crosslinking monomer, α-pinene methacrylate: understanding and exploiting hydrogen abstraction (2022)
Journal Article
Monaghan, O. R., Skowron, S. T., Moore, J. C., Pin-Nó, M., Kortsen, K., Atkinson, R. L., Krumins, E., Lentz, J. C., Machado, F., Onat, Z., Brookfield, A., Collison, D., Khlobystov, A. N., De Focatiis, D., Irvine, D. J., Taresco, V., Stockman, R. A., & Howdle, S. M. (2022). A self-crosslinking monomer, α-pinene methacrylate: understanding and exploiting hydrogen abstraction. Polymer Chemistry, 13(39), 5557-5567. https://doi.org/10.1039/d2py00878e

Crosslinking is a valuable route to creating new polymeric materials and normally involves introduction of a cross linker or some form of secondary processing. Here we report the discovery and analysis of a self-crosslinking sustainable terpene deriv... Read More about A self-crosslinking monomer, α-pinene methacrylate: understanding and exploiting hydrogen abstraction.

Computational investigation of aphid odorant receptor structure and binding function (2022)
Journal Article
Sims, C., Withall, D. M., Oldham, N., Stockman, R., & Birkett, M. (2023). Computational investigation of aphid odorant receptor structure and binding function. Journal of Biomolecular Structure and Dynamics, 41(8), 3647-3658. https://doi.org/10.1080/07391102.2022.2053743

Odorant receptors (OR) play a critical role in signal transduction and olfactory recognition in insects. Unfortunately, insect ORs are difficult to express and purify, and limited structural data are available. Computational methods were used to pred... Read More about Computational investigation of aphid odorant receptor structure and binding function.

Comparative Hydrodynamic Study on Non-Aqueous Soluble Archaeological Wood Consolidants: Butvar B-98 and PDMS-OH Siloxanes (2022)
Journal Article
Cutajar, M., Stockman, R. A., Braovac, S., Steindal, C. C., Zisi, A., & Harding, S. E. (2022). Comparative Hydrodynamic Study on Non-Aqueous Soluble Archaeological Wood Consolidants: Butvar B-98 and PDMS-OH Siloxanes. Molecules, 27(7), Article 2133. https://doi.org/10.3390/molecules27072133

Butvar B-98 and PDMS-OH both have a demonstrable ability as consolidants for archaeological wood. This makes them both potential treatment options for the Oseberg collection, which is one of the most important archaeological finds from the Viking era... Read More about Comparative Hydrodynamic Study on Non-Aqueous Soluble Archaeological Wood Consolidants: Butvar B-98 and PDMS-OH Siloxanes.

Stereodivergent Total Syntheses of (+)‐Monomorine I and (+)‐Indolizidine 195B (2021)
Journal Article
Dawood, R. S., & Stockman, R. A. (2021). Stereodivergent Total Syntheses of (+)‐Monomorine I and (+)‐Indolizidine 195B. European Journal of Organic Chemistry, 2021(27), 3850-3853. https://doi.org/10.1002/ejoc.202100453

A simple and efficient stereoselective total syntheses of two natural products (+)-monomorine I and (+)-indolizidine 195B in high yields starting from a readily available alcohol is described. The key step in this synthetic route exploits the judicio... Read More about Stereodivergent Total Syntheses of (+)‐Monomorine I and (+)‐Indolizidine 195B.

RAFT polymerisation of renewable terpene (meth)acrylates and the convergent synthesis of methacrylate-acrylate-methacrylate triblock copolymers (2021)
Journal Article
Atkinson, R. L., Monaghan, O., Elsmore, M. T., Topham, P. D., Toolan, D. T. W., Derry, M. J., Taresco, V., Stockman, R., De Focatiis, D. S., Irvine, D. J., & Howdle, S. M. (2021). RAFT polymerisation of renewable terpene (meth)acrylates and the convergent synthesis of methacrylate-acrylate-methacrylate triblock copolymers. Polymer Chemistry, 12(21), 3177-3189. https://doi.org/10.1039/d1py00326g

Terpenes are ideal candidates for sustainable polymer feedstocks, due to their natural abundance and availability from existing waste streams. Previously, we have shown that a range of terpene(meth)acrylate monomers can be synthesised from the most c... Read More about RAFT polymerisation of renewable terpene (meth)acrylates and the convergent synthesis of methacrylate-acrylate-methacrylate triblock copolymers.

Iridoid Sex Pheromone Biosynthesis in Aphids Mimics Iridoid‐Producing Plants (2021)
Journal Article
Partridge, S. J., Withall, D. M., Caulfield, J. C., Pickett, J. A., Stockman, R. A., Oldham, N. J., & Birkett, M. A. (2021). Iridoid Sex Pheromone Biosynthesis in Aphids Mimics Iridoid‐Producing Plants. Chemistry - A European Journal, 27(25), 7231-7234. https://doi.org/10.1002/chem.202001356

Biosynthesis of (1R,4aS,7S,7aR)‐nepetalactol (1) and (4aS,7S,7aR)‐nepetalactone (2) in plants involves iridoid synthase (ISY), an atypical reductive cyclase that catalyses the reduction of 8‐oxogeranial into the reactive enol of (S)‐8‐oxocitronellal,... Read More about Iridoid Sex Pheromone Biosynthesis in Aphids Mimics Iridoid‐Producing Plants.

Terpene polyacrylate TPA5 shows favorable molecular hydrodynamic properties as a potential bioinspired archaeological wood consolidant (2021)
Journal Article
Cutajar, M., Andriulo, F., Thomsett, M. R., Moore, J. C., Couturaud, B., Howdle, S. M., Stockman, R. A., & Harding, S. E. (2021). Terpene polyacrylate TPA5 shows favorable molecular hydrodynamic properties as a potential bioinspired archaeological wood consolidant. Scientific Reports, 11(1), Article 7343. https://doi.org/10.1038/s41598-021-86543-1

There is currently a pressing need for the development of novel bioinspired consolidants for waterlogged, archaeological wood. Bioinspired materials possess many advantages, such as biocompatibility and sustainability, which makes them ideal to use i... Read More about Terpene polyacrylate TPA5 shows favorable molecular hydrodynamic properties as a potential bioinspired archaeological wood consolidant.

Tert-butyldimethylsilyl chitosan synthesis and characterization by analytical ultracentrifugation, for archaeological wood conservation (2020)
Journal Article
Wakefield, J. M. K., Braovac, S., Kutzke, H., Stockman, R. A., & Harding, S. E. (2020). Tert-butyldimethylsilyl chitosan synthesis and characterization by analytical ultracentrifugation, for archaeological wood conservation. European Biophysics Journal, 49, 781-789. https://doi.org/10.1007/s00249-020-01450-z

The Oseberg ship is one of the most important archaeological testimonies of the Vikings. After excavation in 1904, the wooden gravegoods were conserved using alum salts. This resulted in extreme degradation of a number of the objects a hundred years... Read More about Tert-butyldimethylsilyl chitosan synthesis and characterization by analytical ultracentrifugation, for archaeological wood conservation.

Synthetic approaches and applications of sulfonimidates (2020)
Journal Article
Matos, P. M., & Stockman, R. A. (2020). Synthetic approaches and applications of sulfonimidates. Organic and Biomolecular Chemistry, 18(33), 6429-6442. https://doi.org/10.1039/d0ob01191f

This review article explores the synthesis of the organosulfur(VI) species named sulfonimidates, focusing on their synthesis from sulfur(II), sulfur(IV) and sulfur(VI) reagents, and investigates their recent resurgeance in interest as intermediates t... Read More about Synthetic approaches and applications of sulfonimidates.

General Method for the Asymmetric Synthesis of N–H Sulfoximines via C–S Bond Formation (2020)
Journal Article
Mendonça Matos, P., Lewis, W., Argent, S. P., Moore, J. C., & Stockman, R. A. (in press). General Method for the Asymmetric Synthesis of N–H Sulfoximines via C–S Bond Formation. Organic Letters, 22(7), 2776-2780. https://doi.org/10.1021/acs.orglett.0c00761

A versatile method for the synthesis of enantioenriched N–H sulfoximines is reported. The approach stems from the organomagnesium-mediated ring opening of novel cyclic sulfonimidate templates. The reactions proceed in high yield and with excellent st... Read More about General Method for the Asymmetric Synthesis of N–H Sulfoximines via C–S Bond Formation.