Derivatives of 3,4-dihydro-β-carboline-3-carboxylic acid from C-terminal tryptophan-containing peptides. Synthesis and properties

Article abstract of DOI:10.1002/jhet.5570250444

C-terminal tryptophan containing peptides have been converted into 1-peptidyl-3,4-dihydro-β-carboline-3-carboxylic acids by acid catalyzed isomerization of their azlactone derivatives. The main properties of these abnormal peptides are a strong absorption around 360 nm an intense fluoroscence and ability to generate reactive carbanions when dissolved in basic media. This tryptophan conversion takes place with high yield and is of general applicability.