Sequence sensitivity and pH dependence of maleimide conjugated N‐terminal cysteine peptides to thiazine rearrangement

Thiazine formation during the conjugation of N‐terminal cysteine peptides to maleimides is an underreported side reaction in the peptide literature. When the conjugation was performed at neutral and basic pH, we observed the thiazine isomer as a significant by‐product. Nuclear magnetic resonance (NMR) spectroscopy confirmed the structure of the six‐membered thiazine and ultra‐high performance liquid chromatography (UHPLC) combined with tandem...