Diazo ester insertion in NH bonds of amino acid derivatives and insulin catalyzed by water-soluble iron and ruthenium porphyrin complexes (FeTSPPCl) as application of carbenoid transfer in aqueous media

•We report diazo ester insertion in NH bonds of amino acid derivatives.•Sulfonated iron porphyrin is an active catalyst for carbenoid insertion in NH bonds of aminoacid derivatives in aqueous media.•Insertion is regioselective onto the NH2 termini of chain B of insulin.

The metal complex FeTSPPCl (5,10,15,20-tetrakis)-(4-sulfonato-phenyl)-porphyrin-iron(III) chloride is an active catalyst for carbenoid insertion in NH bonds of aminoacid derivatives in aqueous media. A variety of diazoacetates and methyl diazophosphonate were used as carbenoid precursors. The commercially available iron porphyrin complex can also selectively catalyze alkylation of the N-terminus of insulin (chain B).

Graphical abstractDiazo ester insertion in NH bonds of amino acid derivatives and insulin catalyzed by water-soluble iron and ruthenium porphyrin complexes as application of carbenoid transfer in aqueous media.Figure optionsDownload full-size imageDownload high-quality image (126 K)Download as PowerPoint slide