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The use of tyrosinases in a chemoenzymatic cascade as a peptide ligation strategy

Ni, Yeke; Wang, Yu; Tabor, Alethea B; Ward, John M; Hailes, Helen C; (2023) The use of tyrosinases in a chemoenzymatic cascade as a peptide ligation strategy. RSC Chemical Biology 10.1039/d2cb00237j. (In press). Green open access

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Abstract

Peptides play many key roles in biological systems and numerous methods have been developed to generate both natural and unnatural peptides. However, straightforward, reliable coupling methods that can be achieved under mild reactions conditions are still sought after. In this work, a new N-terminal tyrosine-containing peptide ligation method with aldehydes, utilising a Pictet–Spengler reaction is described. In a key step, tyrosinase enzymes have been used to convert L-tyrosine to L-3,4-dihydroxyphenyl alanine (L-DOPA) residues, generating suitable functionality for the Pictet–Spengler coupling. This new chemoenzymatic coupling strategy can be used for fluorescent-tagging and peptide ligation purposes.

Type: Article
Title: The use of tyrosinases in a chemoenzymatic cascade as a peptide ligation strategy
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/d2cb00237j
Publisher version: https://doi.org/10.1039/D2CB00237J
Language: English
Additional information: This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Engineering Science > Dept of Biochemical Engineering
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/10162172
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