The metal complexes of N-confused porphyrin as heme model compounds

Journal of Inorganic Biochemistry
John D Harvey, Christopher J Ziegler

Abstract

Recently, metal complexes of the isomers and analogs of porphyrin have become important model compounds for heme enzymes and proteins. While the chemistry of metalloporphyrins as heme models still attracts attention, the isomers and analogs of porphyrins provide insight into the biological choice of porphine as the macrocycle of choice and also help model reactive intermediates, such as high valent oxidation states. In this mini-review, we discuss the heme-relevant chemistry of N-confused porphyrin, an isomer of porphyrin with an inverted pyrrole ring, and focus on the chemistry of manganese, iron, and cobalt. The metallation chemistry of this macrocycle is more diverse than normal porphyrin, and involves tautomerization, C-H bond activation, the Lewis basicity of the external nitrogen, and issues with nucleophilic sensitivity. Despite the challenges posed by N-confused porphyrin, significant progress has been made toward generating heme-model complexes with this macrocycle.

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Citations

Oct 18, 2013·The Journal of Physical Chemistry. a·Christopher J ZieglerVictor N Nemykin
Apr 1, 2017·The Journal of Organic Chemistry·Julia M FisherG Richard Geier
Jan 26, 2008·Chemical Communications : Chem Comm·Anil CetinChristopher J Ziegler
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Feb 29, 2008·Angewandte Chemie·Norbert Jux
Nov 6, 2008·Chemical Communications : Chem Comm·Hua-Wei JiangYu-Cheng Gu
Jul 21, 2009·Chemical Communications : Chem Comm·Saovalak SripothongnakChristopher J Ziegler
Sep 9, 2011·Chemical Communications : Chem Comm·Motoki Toganoh, Hiroyuki Furuta
Mar 1, 2012·Chemistry : a European Journal·Motoki ToganohHiroyuki Furuta

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