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

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dc.contributor.authorScroggie, Kymberley R
dc.contributor.authorAlcock, Lisa J
dc.contributor.authorMatos, Maria J
dc.contributor.authorBernardes, Goncalo J L
dc.contributor.authorPerkins, Michael Victor
dc.contributor.authorChalker, Justin M
dc.date.accessioned2018-10-04T03:10:24Z
dc.date.available2018-10-04T03:10:24Z
dc.date.issued2018-03-13
dc.descriptionThis is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.en_US
dc.description.abstractA 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.en_US
dc.description.sponsorshipAustralian Research Council, Grant Number: DE150101863; The Royal Society (University Research Fellowship; the EPSRC; the European Research Council (Starting Grant); FCT Portugalen_US
dc.identifier.citationScroggie, K. R., Alcock, L. J., Matos, M. J., Bernardes, G. J. L., Perkins, M. V. & Chalker, J. M., (2018). 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. Peptide Science, 110:e24069.en_US
dc.identifier.doihttps://doi.org/10.1002/pep2.24069en_US
dc.identifier.issn1097-0282
dc.identifier.urihttp://hdl.handle.net/2328/38355
dc.language.isoenen_US
dc.oaire.license.condition.licenseCC-BY
dc.publisherWileyen_US
dc.relation.grantnumberARC/DE150101863en_US
dc.rightsThis is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. © 2018 The Authors Peptide Science Published by Wiley Periodicals, Inc.en_US
dc.rights.holder© 2018 The Authors Peptide Science Published by Wiley Periodicals, Inc.en_US
dc.subjectamino acidsen_US
dc.subjectfluorinationen_US
dc.subjectoxidative cleavageen_US
dc.subjectPETen_US
dc.subjectsiliconen_US
dc.subjectStrecker synthesisen_US
dc.titleA silicon-labelled amino acid suitable for late-stage fluorination and unexpected oxidative cleavage reactions in the preparation of a key intermediate in the Strecker synthesisen_US
dc.typeArticleen
local.contributor.authorOrcidLookupChalker, Justin M: https://orcid.org/0000-0002-7504-5508en_US
local.contributor.authorOrcidLookupPerkins, Michael Victor: https://orcid.org/0000-0003-1706-2315en_US
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