Chemistry, Physics & Earth Sciences

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Publications produced by staff from the School of Chemistry, Physics & Earth Sciences.

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Browsing Chemistry, Physics & Earth Sciences by Author "Alcock, Lisa J"
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    Norbornene probes for the study of cysteine oxidation
    (Elsevier, 2017-11-04) Alcock, Lisa J ; Farrell, Kyle D ; Akol, Mawey T ; Jones, Gregory H ; Tierney, Matthew M ; Kramer, Holger B ; Pukala, Tara L ; Bernardes, Goncalo J L ; Perkins, Michael Victor ; Chalker, Justin M
    Cysteine residues on proteins can react with cellular oxidants such as hydrogen peroxide. While this process is important for scavenging excess reactive oxygen species, the products of this oxidation may also mediate cell signalling. To understand the role of cysteine oxidation in biology, selective probes are required to detect and quantify its occurrence. Cysteine oxidation products such as sulfenic acids are sometimes unstable and therefore short-lived. If such cysteine derivatives are to be analysed, rapid reaction with the probe is required. Here we introduce norbornene derivatives as probes for cysteine oxidation, and demonstrate their ability to trap sulfenic acids. The synthesis of norbornene derivatives containing alkyne or biotin affinity tags are also reported to facilitate the use of these probes in chemical biology and proteomics.
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    A silicon-labelled amino acid suitable for late-stage fluorination and unexpected oxidative cleavage reactions in the preparation of a key intermediate in the Strecker synthesis
    (Wiley, 2018-03-13) Scroggie, Kymberley R ; Alcock, Lisa J ; Matos, Maria J ; Bernardes, Goncalo J L ; Perkins, Michael Victor ; Chalker, Justin M
    A novel silicon-substituted phenylalanine derivative was prepared using the Strecker amino acid synthesis. An unexpected oxidative cleavage was observed in the preparation of the aldehyde required for the Strecker reaction. In this step, a homobenzylic alcohol intermediate was oxidatively cleaved to the corresponding benzaldehyde using either chromium or palladium based oxidants. This undesired side reaction was overcome through the use of Dess-Martin Periodinane, or through an efficient TEMPO-bleach oxidation. The amino acid prepared in this study was then labelled with fluoride in aqueous solvent using a range of fluoride sources. The efficiency of this labelling motivates future studies in late-stage fluorination of peptide and protein therapeutics for use in positron emission tomography.