Direkter Nachweis einer Wasserstoffbrücke zu gebundenem Disauerstoff in einem Modellkomplex für Myoglobin/Hämoglobin und in Cobalt‐Myoglobin durch Puls‐EPR

Dube, Henry; Kasumaj, Besnik; Calle, Carlos I.; Saito, Makoto; Jeschke, Gunnar; Diederich, François

doi:10.1002/ange.200705180

Cited by 15 publications

(18 citation statements)

References 28 publications

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“…[4] Zinc ions were inserted into the obtained free-base porphyrin 15-2H to yield the corresponding complex 15-Zn to which 1-(6-bromohexyl)imidazole (16) [11] was attached to yield 17-Zn. After removal of the iPr 3 Si group, porphyrin 18-Zn was obtained in 93 % yield.…”

Section: Synthesismentioning

confidence: 99%

“…24,H 5.78,N 7.84;found: C 67.41,H 5.95,N 7.70. (Tetraethyl 4,4',4'',[4][5][6][7][8][9][10]-5-{ [6-(1H-imidazol-1-yl)hexyl]oxy}phenyl)porphyrin-5,15-diyl-kN 21 ,kN 22 ,kN 23 ,kN 24 ]bis[benzene-2,1,3-triylbisA C H T U N G T R E N N U N G (oxy)]}tetrabutanoato(2À))zinc (4-Zn): The title compound was prepared from 18-Zn (50 mg, 0.04 mmol) according to the general procedure using iodinated precursor 21. Yield 40 mg (74 %); m.p.…”

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confidence: 99%

“…Yield 40 mg (74 %); m.p. 102-104 8C; (Tetraethyl 4,4',4'',(4)(5)(6)(7)(8)(9)(10)hexyl]oxy}phenyl)porphyrin-5,15-diyl-kN 21 ,kN 22 ,kN 23 ,…”

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confidence: 99%

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Probing Hydrogen Bonding to Bound Dioxygen in Synthetic Models for Heme Proteins: The Importance of Precise Geometry

Dube

Kasumaj

Calle

et al. 2008

Chemistry A European J

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Distal hydrogen bonding in natural dioxygen binding proteins is crucial for the discrimination between different potential ligands such as O(2) or CO. In the present study, we probe the chemical requirements for proper distal hydrogen bonding in a series of synthetic model compounds for dioxygen-binding heme proteins. The model compounds 1-Co to 7-Co bear different distal residues. The hydrogen bonding in their corresponding dioxygen adducts is directly measured by pulse EPR spectroscopy. The geometrical requirements for this interaction to take place were found to be narrow and very specific. Only two model complexes, 1-Co and 7-Co, form a hydrogen bond to bound dioxygen, which was characterized in terms of geometry and nature of the bond. The geometry and dipolar nature of this interaction in 1-Co-O(2) is more similar to the one in natural cobalt myoglobin (Co-Mb), making 1-Co the best model compound in the entire series.

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Section: Synthesismentioning

confidence: 99%

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confidence: 99%

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Probing Hydrogen Bonding to Bound Dioxygen in Synthetic Models for Heme Proteins: The Importance of Precise Geometry

Dube

Kasumaj

Calle

et al. 2008

Chemistry A European J

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“…B. Halogenid oder Cyanid) und wegen der nun fehlenden Chelatisierung zu einer insgesamt flexibleren Struktur. [27] Die katalytische Aktivität von Strukturen, die über diese Ansätze der supramolekularen Koordinationschemie hergestellt wurden, kann hinsichtlich der katalytischen Erhöhung der Reaktionsgeschwindigkeit über Naheffekte in Käfi-gen, [10l, 28] [2, 3,5,[7][8][9]30] Ein wichtiger Gesichtspunkt ist dabei die Aufklärung der Rolle von Mangan-und Eisenporphyrinen bei katalytischen Oxidationen. [31] Viele dieser Systeme entstehen aber nicht durch supramolekulare Koordinationschemie, sondern als Produkte mehrstufiger organischer Synthesen, sodass sie nicht in den Themenbereich dieses Aufsatzes fallen.…”

Section: Ansätze Der Supramolekularen Koordinationschemieunclassified

Enzymnachbildungen auf der Basis supramolekularer Koordinationschemie

2010

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In der aktuellen supramolekularen Koordinationschemie können makromolekulare Komplexe mit Enzymeigenschaften synthetisiert werden. Dieser Aufsatz behandelt solche Strukturen, die nicht in erster Linie die aktiven Zentren von Enzymen nachbilden sollen, sondern von deren Eigenschaften und Funktionen inspiriert sind. Die Komplexe werden in konvergenter Weise mit modularen Methoden in hohen Ausbeuten synthetisiert, wobei ihre Größe, Form und Eigenschaften maßgeschneidert werden können. Viele der Strukturen zeigen eine Reaktivität und Spezifität, die an natürliche Systeme erinnern, und manche haben Funktionen, die über jene ihrer Vorbilder hinausgehen.

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“…Until now, great efforts have been made on the research of the effect of hydrogen bonds in photochemistry and photobiology, and also on the hydrogen-bonding dynamics that appreciably control the dynamics of hydrogenbonded complexes [24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39]. Recently, the relationship between electronic spectral shifts and electronic excited- * E-mail: haoce_dlut@126.com state hydrogen-bonding dynamics has been illustrated by Zhao and Han for the first time.…”

Section: Introductionmentioning

confidence: 99%

A theoretical forecast of the hydrogen bond changes in the electronic excited state for BN and its derivatives

Wang¹,

Hao²,

Wang³

et al. 2011

Open Physics

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Ê Ú ¼ ÖÙ ÖÝ ¾¼½½ ÔØ ¼ Ù Ù×Ø ¾¼½½ ×ØÖ ØThe relationship between electronic spectral shifts and hydrogen-bonding dynamics in electronically excited states of the hydrogen-bonded complex is put forward. Hydrogen bond strengthening will induce a redshift of the corresponding electronic spectra, while hydrogen bond weakening will cause a blueshift. Time-dependent density function theory (TDDFT) was used to study the excitation energies in both singlet and triplet electronically excited states of Benzonitrile (BN), 4-aminobenzonitrile (ABN), and 4-dimethylaminobenzonitrile (DMABN) in methanol solvents. Only the intermolecular hydrogen bond C≡N· · · H-O was involved in our system. A fairly accurate forecast of the hydrogen bond changes in lowlying electronically excited states were presented in light of a very thorough consideration of their related electronic spectra. The deduction we used to depict the trend of the hydrogen bond changes in excited states could help others understand hydrogen-bonding dynamics more effectively.

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Direkter Nachweis einer Wasserstoffbrücke zu gebundenem Disauerstoff in einem Modellkomplex für Myoglobin/Hämoglobin und in Cobalt‐Myoglobin durch Puls‐EPR

Cited by 15 publications

References 28 publications

Probing Hydrogen Bonding to Bound Dioxygen in Synthetic Models for Heme Proteins: The Importance of Precise Geometry

Probing Hydrogen Bonding to Bound Dioxygen in Synthetic Models for Heme Proteins: The Importance of Precise Geometry

Enzymnachbildungen auf der Basis supramolekularer Koordinationschemie

A theoretical forecast of the hydrogen bond changes in the electronic excited state for BN and its derivatives

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