Organic chemistry

Enzyme

Combinatorial chemistry

Cysteine

Biology

Biophysics

Biomedical engineering

Chemistry

Peptide

Protecting group

Group (periodic table)

Thiol

Alkyl

Scaffold

Biochemistry

Medicine

Chemical Communications

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.

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