C-H bond amination is an effective way to obtain nitrogen-containing products. In this work, we demonstrate that myoglobin reconstituted with iron porphycene (rMb(FePc)) catalyzes intramolecular C(sp)-H bond amination of arylsulfonyl azides to yield corresponding sultam analogs. The total turnover number of rMb(FePc) is up to 5.7 × 10 for the C-H bond amination of 2,4,6-triisopropylbenzenesulfonyl azide. Moreover, rMb(FePc) exhibits higher selectivity for the desired C-H bond amination than the competing azide reduction compared to native myoglobin. Kinetic studies reveal that the k value of rMb(FePc) is 4-fold higher than that of native myoglobin. Furthermore, H64A, H64V and H64I mutants of rMb(FePc) enhance the turnover number (TON) and enantioselectivity for the C-H bond amination of 2,4,6-triethylbenzenesulfonyl azide. The present findings indicate that iron porphycene is an attractive artificial cofactor for myoglobin toward the C-H bond amination reaction.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.jinorgbio.2023.112459 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Effect of Irrigation Solution Temperature on Bioceramic Sealer Bond Strength.
Med Sci Monit
January 2025
Department of Endodontics, Faculty of Dentistry, Dicle University, Diyarbakir, Turkey.
BACKGROUND Different temperature conditions can affect the efficiency of irrigation solutions and consequently the ability of canal sealers to bond to root canal walls. The aim of this endodontic study was to evaluate the effect of irrigation solutions at different temperatures on the bond strength of a bioceramic-based root canal sealer. MATERIAL AND METHODS Root canal preparations were completed through irrigation with the following solutions: Group 1 was irrigated with 5 ml NaOCl (sodium hypochlorite) +5 ml EDTA (Ethylenediamine tetra-acetic acid) (22°C); Group 2 was irrigated with 5 ml NaOCl +5 ml EDTA (37°C); Group 3 was irrigated with 5 ml NaOCl +5 ml GA (Glycolic acid) (22°C); Group 4 was irrigated with 5 ml NaOCl +5 ml GA (37°C), Group 5 was irrigated with 20 ml Dual Rinse® HEDP (Etidronate) - NaOCl mixture (22°C); and Group 6 was irrigated with 20 ml of Dual Rinse® HEDP mixture (37°C).
View Article and Find Full Text PDFPhoto-Driven Direct Construction of Imidazolidines from Anilines and Paraformaldehyde and Its Application in Polyoxymethylene Plastics Usage.
Chem Asian J
January 2025
Leibniz-Institut fur Katalyse eV, organmetallic and catalyst, Albert-Einstein-Str. 29a, 18059, Rostock, GERMANY.
Imidazolines play pivotal roles in numerous fields. However, the direct construction of imidazolines from primary amines involves precise C-C and C-N bond formations, rendering this area still underdeveloped to this day. Herein, a photo-driven metal-free catalytic system has been successfully applied to a novel coupling-cyclization reaction between arylamines and formaldehyde, enabling the direct synthesis of various 1,3-diarylimidazolines from primary amines.
View Article and Find Full Text PDFFluorescent Artificial Receptor for Dopamine based on Molecular Recognition-driven Dynamic Covalent Chemistry in a Lipid Nanoreactor.
Angew Chem Int Ed Engl
January 2025
University of Strasbourg, UMR 7213 CNRS, 74, Route du Rhin, 67401, Illkirch-Strasbourg, FRANCE.
Molecular recognition and detection of small bioactive molecules, like neurotransmitters, remain a challenge for chemists, whereas nature found an elegant solution in form of protein receptors. Here, we introduce a concept of a dynamic artificial receptor that synergically combines molecular recognition with dynamic imine bond formation inside a lipid nanoreactor, inducing a fluorescence response. The designed supramolecular system combines a lipophilic recognition ligand derived from a boronic acid, a fluorescent aldehyde based on push-pull styryl pyridine and a phenol-based catalyst.
View Article and Find Full Text PDFSilylformates are emerging surrogates of hydrosilanes, able to reduce carbonyl groups in transfer hydrosilylation reactions, with the concomitant release of CO2. In this work, a new reactivity is revealed for silylformates, in the presence of imines. Using ruthenium catalysts, and lithium iodide as a co-catalyst, imines are shown to undergo hydrocarboxysilylation by formal insertion of CO2 to the N-Si bond of silyl amine to yield silyl carbamates in excellent yields.
View Article and Find Full Text PDFDefect-Induced Electron Localization Promotes D2O Dissociation and Nitrile Adsorption for Deuterated Amines.
Angew Chem Int Ed Engl
January 2025
Tianjin University, Department of Chemistry, #92, Weijin Road, Nankai District, Department of Chemistry, School of Science, Tianjin University, 300072, Tianjin, CHINA.
Electrochemical reductive deuteration of nitriles is a promising strategy for synthesizing deuterated amines with D2O as the deuterated source. However, this reaction suffers from high overpotentials owing to the sluggish D2O dissociation kinetics and high thermodynamic stability of the C≡N triple bond. Here, low-coordinated copper (LC-Cu) is designed to decrease the overpotential for the electrosynthesis of the precursor of Melatonin-d4, 5-methoxytryptamine-d4, by 100 mV with a 68% yield (Faraday efficiency), which is 4 times greater than that of high-coordinated copper (HC-Cu).
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!