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Going Round in Circles with N -> S Acyl Transfer

Macmillan, D; (2017) Going Round in Circles with N -> S Acyl Transfer. Synlett , 28 (13) pp. 1517-1529. 10.1055/s-0036-1588789. Green open access

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Abstract

It is not highly sophisticated, yet the N→S acyl transfer reaction of a native peptide sequence potentially fills an important technology gap. While several routes to synthetic peptide thioesters exist, only one is routinely applicable for biologically derived samples. Using the naturally occurring amino acid cysteine as the sole activator for N→S acyl transfer we have demonstrated transformation of synthetic and biologically derived precursors into thioesters for use in Native Chemical Ligation, providing a viable alternative for biological samples. Further refinement will be key to realising the full potential of this intriguing process, and increase the number of applications in peptide engineering and therapeutics.

Type: Article
Title: Going Round in Circles with N -> S Acyl Transfer
Open access status: An open access version is available from UCL Discovery
DOI: 10.1055/s-0036-1588789
Publisher version: https://doi.org/10.1055/s-0036-1588789
Language: English
Additional information: This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions.
Keywords: thioester - native chemical ligation - cyclic peptides - acyl transfer
UCL classification: UCL
UCL > Provost and Vice Provost Offices
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10060527
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