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

Richard J. Spears; Clíona McMahon; Monika Shamsabadi; Calise Bahou; Ioanna A. Thanasi; Léa N. C. Rochet; Nafsika Forte; Fabien Thoreau; James R. Baker; Vijay Chudasama

doi:10.1039/D1CC03802H

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

Richard J. Spears,

^a Clíona McMahon,^a Monika Shamsabadi,^a Calise Bahou,^a Ioanna A. Thanasi,^a Léa N. C. Rochet,^a Nafsika Forte,^a Fabien Thoreau,^a James R. Baker

*^a and Vijay Chudasama

*^a

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* Corresponding authors

^a UCL Department of Chemistry, 20 Gordon Street, London, UK
E-mail: v.chudasama@ucl.ac.uk, j.r.baker@ucl.ac.uk

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.

Chemical Communications

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

Abstract

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

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