A Simple Synthesis of Dioxoisobacteriochlorins from Hematoporphyrin

Abstract

Hematoporphyrin dimethyl ester 1, available in any desired amount from slaughter houses, can be transformed by a surprisingly simple reaction sequence into complex porphyrin structures of the isobacteriochlorin type such as 2. Such compounds play a key role as coenzymes in sulfite and nitrite reduction in microorganisms and plants.

Magnetic Resonance and Structural Investigations of (Monooxooctaethylchlorinato)iron(III) Chloride and Its Bis(imidazole) Complex

“…Hence, in an attempt to investigate the electronic properties of heme d 1 , we have begun a study of the iron(III) complexes of monooxooctaethylchlorin (oxo-OEC) and dioxooctaethylisobacteriochlorin (dioxo-OEiBC), the latter of which should be a good model for the heme d 1 center. The synthesis of these macrocycles from octaethylporphyrin [24][25][26] and of derivatives of the natural porphyrins from hematoporphyrin 27 has been reported, as has the crystal structure of (oxo-OEC)-FeCl 28 and (dioxo-OEiBC)FeCl. 29 In this work, a second molecular structure of (oxo-OEC)FeCl has been solved, and the 1 H NMR and EPR spectra of its bis(imidazole) complex are reported.…”