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A novel thiol-labile cysteine protecting group for peptide synthesis based on a pyridazinedione (PD) scaffold

Spears, RJ; McMahon, C; Shamsabadi, M; Bahou, C; Thanasi, IA; Rochet, LNC; Forte, N; ... Chudasama, V; + view all (2021) A novel thiol-labile cysteine protecting group for peptide synthesis based on a pyridazinedione (PD) scaffold. Chemical Communications 10.1039/d1cc03802h. (In press). Green open access

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Abstract

Herein we report a thiol-labile cysteine protecting group based on an unsaturated pyridazinedione (PD) scaffold. We establish compatibility of the PD in conventional solid phase peptide synthesis (SPPS), showcasing this in the on-resin synthesis of biologically relevant oxytocin. Furthermore, we establish the applicability of the PD protecting group towards both microwave-assisted SPPS and native chemical ligation (NCL) in a model system.

Type: Article
Title: A novel thiol-labile cysteine protecting group for peptide synthesis based on a pyridazinedione (PD) scaffold
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/d1cc03802h
Publisher version: https://doi.org/10.1039/d1cc03802h
Language: English
Additional information: This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Keywords: Science & Technology, Physical Sciences, Chemistry, Multidisciplinary, Chemistry, DISULFIDE FORMATION
UCL classification: UCL
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/10138702
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