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).

Diazo 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 high-quality image (126 K)Download as PowerPoint slide