A Six-Coordinate Peroxynitrite Low-Spin Iron(III) Porphyrinate Complex—The Product of the Reaction of Nitrogen Monoxide (·NO(g)) with a Ferric-Superoxide Species

Sharma, Savita K.; Schaefer, Andrew W.; Lim, Hyeongtaek; Matsumura, Hirotoshi; Moenne-Loccoz, Pierre; Hedman, Britt; Hodgson, Keith O.; Solomon, Edward I.; Karlin, Kenneth D.

doi:10.1021/jacs.7b08468

A Six-Coordinate Peroxynitrite Low-Spin Iron(III) Porphyrinate Complex—The Product of the Reaction of Nitrogen Monoxide (·NO_(g)) with a Ferric-Superoxide Species

Journal Article · Wed Nov 01 00:00:00 EDT 2017 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.7b08468· OSTI ID:1457149

Sharma, Savita K. ^[1]; Schaefer, Andrew W. ^[2]; Lim, Hyeongtaek ^[2]; Matsumura, Hirotoshi ^[3]; ^[3]; Hedman, Britt ^[4]; Hodgson, Keith O. ^[5]; ^[5]; ^[1]

Johns Hopkins Univ., Baltimore, MD (United States)
Stanford Univ., Stanford, CA (United States)
Oregon Health & Science Univ., Portland, OR (United States)
SLAC National Accelerator Lab., Menlo Park, CA (United States)
Stanford Univ., Stanford, CA (United States); SLAC National Accelerator Lab., Menlo Park, CA (United States)

Peroxynitrite (^–OON=O, PN) is a reactive nitrogen species (RNS) which can effect deleterious nitrative or oxidative (bio)chemistry. It may derive from reaction of superoxide anion (O₂^•–) with nitric oxide (·NO) and has been suggested to form an as-yet unobserved bound heme-iron-PN intermediate in the catalytic cycle of nitric oxide dioxygenase (NOD) enzymes, which facilitate a ·NO homeostatic process, i.e., its oxidation to the nitrate anion. Here, a discrete six-coordinate low-spin porphyrinate-Fe^III complex [(P^Im)Fe^III(^–OON=O)] (P^Im; a porphyrin moiety with a covalently tethered imidazole axial “base” donor ligand) has been identified and characterized by various spectroscopies (UV–vis, NMR, EPR, XAS, resonance Raman) and DFT calculations, following its formation at –80 °C by addition of ·NO_(g) to the heme-superoxo species, [(P^Im)Fe^III(O₂^•–)]. DFT calculations confirm that is a six-coordinate low-spin species with the PN ligand coordinated to iron via its terminal peroxidic anionic O atom with the overall geometry being in a cis-configuration. Complex thermally transforms to its isomeric low-spin nitrato form [(P^Im)Fe^III(NO₃^–)]. While previous (bio)chemical studies show that phenolic substrates undergo nitration in the presence of PN or PN-metal complexes, in the present system, addition of 2,4-di-tert-butylphenol (^2,4DTBP) to complex does not lead to nitrated phenol; the nitrate complex still forms. Furthermore, DFT calculations reveal that the phenolic H atom approaches the terminal PN O atom (farthest from the metal center and ring core), effecting O–O cleavage, giving nitrogen dioxide (·NO₂) plus a ferryl compound [(P^Im)Fe^IV=O] (7); this rebounds to give [(P^Im)Fe^III(NO₃^–)].The generation and characterization of the long sought after ferriheme peroxynitrite complex has been accomplished.

View Accepted Manuscript (DOE)

Research Organization:: SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-76SF00515

OSTI ID:: 1457149

Journal Information:: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 48 Vol. 139; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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