NDLI: Exploring the Strength of the H-Bond in Synthetic Models for Heme Proteins: The Importance of the N−H Acidity of the Distal Base

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Exploring the Strength of the H-Bond in Synthetic Models for Heme Proteins: The Importance of the N−H Acidity of the Distal Base

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Exploring the Strength of the H-Bond in Synthetic Models for Heme Proteins: The Importance of the N−H Acidity of the Distal Base

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Tödtli, Laura Polyhach, Yevhen Jeschke, Gunnar Diederich, François Tzirakis, Manolis D. Alberti, Mariza N.
Description	Author Affiliation: Alberti MN ( Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093, Zurich, Switzerland.); Polyhach Y ( Laboratory of Physical Chemistry, ETH Zurich, Vladimir-Prelog-Weg 2, 8093, Zurich, Switzerland.); Tzirakis MD ( Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093, Zurich, Switzerland.); Tödtli L ( Laboratory of Physical Chemistry, ETH Zurich, Vladimir-Prelog-Weg 2, 8093, Zurich, Switzerland.); Jeschke G ( Laboratory of Physical Chemistry, ETH Zurich, Vladimir-Prelog-Weg 2, 8093, Zurich, Switzerland. gunnar.jeschke@phys.chem.ethz.ch.); Diederich F ( Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093, Zurich, Switzerland. diederich@org.chem.ethz.ch.)
Abstract	The distal hydrogen bond (H-bond) in dioxygen-binding proteins is crucial for the discrimination of $O_{2}$ with respect to CO or NO. We report the preparation and characterization of a series of $Zn^{II}$ porphyrins, with one of three meso-phenyl rings bearing both an alkyl-tethered proximal imidazole ligand and a heterocyclic distal H-bond donor connected by a rigid acetylene spacer. Previously, we had validated the corresponding $Co^{II}$ complexes as synthetic model systems for dioxygen-binding heme proteins and demonstrated the structural requirements for proper distal H-bonding to $Co^{II}-bound$ dioxygen. Here, we systematically vary the H-bond donor ability of the distal heterocycles, as predicted based on $pK_{a}$ values. The H-bond in the dioxygen adducts of the $Co^{II}$ porphyrins was directly measured by Q-band Davies-ENDOR spectroscopy. It was shown that the strength of the hyperfine coupling between the dioxygen radical and the distal H-atom increases with enhanced acidity of the H-bond donor.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	29
Volume Number	22
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2016-07-11
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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