Diazo ester insertion in N-H 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

Hassan F. Srour (1) , Paul Le Maux (1) , Soizic Chevance (1) , Daniel Carrié (1) , Nicolas Le Yondre (2) , Gérard Simonneaux (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 CRMPO - Centre Régional de Mesures Physiques de l'Ouest

The metal complex FeTSPPCl (5,10,15,20-tetrakis)-(4-sulfonato-phenyl)-porphyrin-iron(III) chloride is an active catalyst for carbenoid insertion in N–H 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)

Keywords: amino ester; Catalytic NH insertion; diazo ester; Insulin; iron porphyrin

Domains: Chemical Sciences

Hassan F. Srour, Paul Le Maux, Soizic Chevance, Daniel Carrié, Nicolas Le Yondre, et al.. Diazo ester insertion in N-H 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. Journal of Molecular Catalysis A: Chemical, 2015, 407, pp.194-203. ⟨10.1016/j.molcata.2015.06.028⟩. ⟨hal-01174902⟩