Characterization of several novel iron nitrosyl porphyrins

Olson, Larry W.; Schaeper, D.; Lançon, D.; Kadish, Karl M.

doi:10.1021/ja00371a051

Cited by 71 publications

(65 citation statements)

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“…21 Exchange of 18 O into the substrate NO has also been demonstrated. 111 Known potentials for the heme Fe 2+ -NO/heme Fe 2+ -NO + couple range from +0.39 to -0.02V, 53,54 well within the physiologically accessible range, suggesting that an oxidized heme-nitrosyl species similar to that encountered in the reaction of the heme cd 1 nitrite reductase may be responsible.…”

Section: A Bacterial Nitric Oxide Reductasesmentioning

confidence: 95%

“…-0.9 V and do not depend greatly on the nature of the heme (porphyrin vs dihydroporphyrin vs tetrahydroporhyrin) 53 or on the nature of the ligand trans to the NO. 54 This is almost a volt more negative than the potential of physiological reductants such as succinate (Table 1). It is therefore difficult to see how the enzyme could produce NO -bound to a heme.…”

Section: A Bacterial Nitric Oxide Reductasesmentioning

confidence: 99%

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Dissimilatory Nitrite and Nitric Oxide Reductases

1996

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Section: A Bacterial Nitric Oxide Reductasesmentioning

confidence: 95%

Section: A Bacterial Nitric Oxide Reductasesmentioning

confidence: 99%

Dissimilatory Nitrite and Nitric Oxide Reductases

1996

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“…14 This result is in strong contrast to the non-heme {FeNO} 7 , where the reduction is centered on the iron in forming the {FeNO} 8 complex. 41 This difference is also reflected in the redox potentials, which is much more negative for the heme {Fe-NO} 7 complexes.…”

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confidence: 99%

X-ray Structure and Properties of the Ferrous Octaethylporphyrin Nitroxyl Complex

et al. 2016

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Synopsis:The X-ray crystal structure of [Fe(OEP) (NO)]− is reported, along with infrared and NMR spectra. The Fe−N−O bond angle decreased upon reduction and was consistent with those in other {FeNO} 8 complexes. The 1 H NMR spectrum was reported, which was different from those for other S = 0 metalloporphyrin complexes due to the displacement of the Fe atom from the porphyrin plane. This spectrum was consistent with DFT calculations.NOT THE PUBLISHED VERSION; this is the author's final, peer-reviewed manuscript. The published version may be accessed by following the link in the citation at the bottom of the page.Inorganic Chemistry, Vol 55, No. 5 (2016): pg. 2070-2075. DOI. This article is © American Chemical Society and permission has been granted for this version to appear in e-Publications@Marquette. American Chemical Society does not grant permission for this article to be further copied/distributed or hosted elsewhere without the express permission from American Chemical Society. 2 AbstractThe preparation and characterization of the iron octaethylporphyrin nitroxyl ion, [Fe(OEP), is reported. The complex was synthesized by the oneelectron reduction of Fe(OEP)(NO) using anthracenide as the reducing agent. The compound was isolated as the potassium (2.2.2)cryptand salt. The anion was characterized using X-ray analysis with visible and infrared spectroscopy. The spectral features of the iron nitroxyl complex were consistent with previous literature reports. The important structural changes upon reduction were a significant decrease in the Fe-N-O bond angle from 142° to 127° and an increase in the N-O bond length from that in the starting nitrosyl moiety. The porphyrin ring became significantly less planar upon reduction, but the displacement of the iron atom from the 24-atom plane was essentially unchanged. In spite of the attempt to encapsulate the potassium ion with the (2.2.2)cryptand, significant interaction between K + and the oxygen of the nitroxyl were observed, indicating a contact ion pair in the crystal structure. Comparison between the experimental structure and the DFT-calculated parameters were reported. The results are consistent with the Fe-N-O moiety being the site of the reduction, with little evidence for the reduction of the iron itself or the porphyrin ring. The proton NMR spectrum was also obtained, NOT THE PUBLISHED VERSION; this is the author's final, peer-reviewed manuscript. The published version may be accessed by following the link in the citation at the bottom of the page.Inorganic Chemistry, Vol 55, No. 5 (2016): pg. 2070-2075. DOI. This article is © American Chemical Society and permission has been granted for this version to appear in e-Publications@Marquette. American Chemical Society does not grant permission for this article to be further copied/distributed or hosted elsewhere without the express permission from American Chemical Society.3 and the chemical shifts were significantly different from other S = 0 metalloporphyrin complexes. These shifts, though, were consistent wit...

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“…One approach is to introduce a modification into the furanose moieties. The gauche-effect from an electronegative group at the 2Ј-position has been shown to shift the conformational equilibrium toward the North conformers (largely 3Ј-endo), [8,9] which in general results in oligonucleotide analogues with increased hybridization affinity towards complementary RNA. [10,11] Recent studies of oligonucleotide than that obtained by tert-butyldimethylsilyl protection, when 9-BBN-H was used as reagent.…”

Section: Introductionmentioning

confidence: 99%

“…The ribo isomer was converted into the corresponding mesylate 6 to allow for further functionalization. Subsequent substitution with azide and reduction afforded 1-[3-C-aminomethyl-2-O-(tert-butyldimethylsilyl)-3-deoxy-5-O-(4-methoxytrityl)-β-D-ribo-pentofuranosyl]uracil (8) in good overall yield (43% over 6 steps).…”

Section: Introductionmentioning

confidence: 99%