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Structure and Bonding in Heme–Nitrosyl Complexes and Implications for Biology

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Nitrosyl Complexes in Inorganic Chemistry, Biochemistry and Medicine II

Part of the book series: Structure and Bonding ((STRUCTURE,volume 154))

Abstract

This review summarizes our current understanding of the geometric and electronic structures of ferrous and ferric heme–nitrosyls, which are of key importance for the biological functions and transformations of NO. In-depth correlations are made between these properties and the reactivities of these species. Here, a focus is put on the discoveries that have been made in the last 10 years, but previous findings are also included as necessary. Besides this, ferrous heme–nitroxyl complexes are also considered, which have become of increasing interest recently due to their roles as intermediates in NO and multiheme nitrite reductases, and because of the potential role of HNO as a signaling molecule in mammals. In recent years, computational methods have received more attention as a means of investigating enzyme reaction mechanisms, and some important findings from these theoretical studies are also highlighted in this chapter.

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Abbreviations

2-MI:

2-Methylimidazole

3,5-Me-BAFP:

3,5-Methyl-bis(aryloxy)-fence porphyrin

4-MePip:

4-Methylpiperidine

5C:

Five-coordinate

6C:

Six-coordinate

CcNIR:

Multiheme cytochrome c nitrite reductase

CcO:

Cytochrome c oxidase

Cys:

Cysteine, cysteinate

Cyt c :

Cytochrome c

Deut2− :

Deuteroporphyrin IX dimethylester dianion

ENDOR:

Electron-nuclear double resonance spectroscopy

eNOS:

Endothelial nitric oxide synthase

EPR:

Electron paramagnetic resonance spectroscopy

Hb:

Hemoglobin

His:

Histidine

HNOX:

Heme-nitric oxide or oxygen binding (domain)

HOMO:

Highest occupied molecular orbital

HRP:

Horseradish peroxidase

hs:

High-spin

iNOS:

Inducible nitric oxide synthase

Iz:

Indazole

ls:

Low-spin

LUMO:

Lowest unoccupied molecular orbital

Mb:

Myoglobin

MCD:

Magnetic circular dichroism spectroscopy

MI:

1-Methylimidazole (also called N-methylimidazole)

MO:

Molecular orbital

NIR:

Nitrite reductase

nNOS:

Neuronal nitric oxide synthase

NO:

Nitric oxide

NOD:

Nitric oxide dioxygenation

NOR:

Nitric oxide reductases

NorBC:

Bacterial respiratory NO reductase

NOS:

Nitric oxide synthase

Np:

Nitrophorins

NRVS:

Nuclear resonance vibrational spectroscopy

OEP2− :

Octaethylporphyrin dianion

OETPP2− :

Octaethyltetraphenylporphyin dianion

oxoOEC2− :

Oxooctaethylchlorin

P2− :

Porphine dianion

P450nor:

Fungal cytochrome P450 NO reductase

p-C6H4F− :

4-Fluorophenyl anion

PCET:

Proton-coupled electron transfer

PES:

Potential energy surface

Prz:

Pyrazine

Py:

Pyridine

Pz:

Pyrazole

rNp:

Rhodnius prolixus nitrophorins

sGC:

Soluble guanylate cyclase

SOMO:

Singly occupied molecular orbital

To-F2PP2− :

Tetra(ortho-difluoro-phenyl)-porphyrin dianion

Tp-CF3PP2− :

Tetra(para-trifluoromethylphenyl)-porphyrin dianion

Tp-FPP2− :

Tetra(para-fluorophenyl)-porphyrin dianion

TpivPP2− :

Picket fence porphyrin

Tp-NO2PP2− :

Tetra(para-nitrophenyl)-porphyrin dianion

Tp-OCH3PP2− :

Tetra(para-methoxyphenyl)-porphyrin dianion

TPP*2− :

Phenyl-substituted tetraphenylporphyrin dianion

TPP2− :

Tetraphenylporphyrin dianion

TPPBr4 2− :

2,3,12,13-Tetrabromotetraphenylporphyrin dianion

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Authors and Affiliations

  1. Department of Chemistry, The University of Michigan, Ann Arbor, MI, 48109-1055, USA

    Nicolai Lehnert & Matthew W. Wolf

  2. Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, IN, 46556, USA

    W. Robert Scheidt

Authors
  1. Nicolai Lehnert
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  2. W. Robert Scheidt
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  3. Matthew W. Wolf
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Correspondence to Nicolai Lehnert or W. Robert Scheidt .

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  1. Inorganic Chemistry Laboratory, University of Oxford, Oxford, United Kingdom

    D. Michael P. Mingos

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Lehnert, N., Scheidt, W.R., Wolf, M.W. (2013). Structure and Bonding in Heme–Nitrosyl Complexes and Implications for Biology. In: Mingos, D. (eds) Nitrosyl Complexes in Inorganic Chemistry, Biochemistry and Medicine II. Structure and Bonding, vol 154. Springer, Berlin, Heidelberg. https://doi.org/10.1007/430_2013_92

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