The asymmetric reduction of acetophenone with sodium borohydride in the presence of β-cyclodextrin (β-CD) as catalyst can improve selectivity and yield. The interaction between acetophenone and β-CD plays an important role for the reduction of acetophenone. This work studies the reaction of acetophenone in the presence of β-CD using density functional theory (DFT) method. Energy is investigated to find out the lowest energy of two possible complexation models. The geometrical structure confirms that acetophenone inserts into the cavity mainly from the secondary hydroxyl side. Hydrogen bonds are researched on the basis of natural bonding orbital (NBO) analysis, the results confirm the donor-acceptor interactions of complex. Mülliken charge and frontier orbital are employed for revealing the electronic transfer. In addition, (13)C nuclear magnetic resonance ((13)CNMR) spectroscopy shows that the active site concentrates on the carbon atom of carbonyl group. The probable catalytic mechanism of β-CD is discussed in terms of the calculated parameters.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1007/s00894-014-2268-7 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Substrate expansion of Geotrichum candidum alcohol dehydrogenase towards diaryl ketones by mutation.
Appl Microbiol Biotechnol
December 2024
Department of Life Science and Technology: Tokyo Kogyo Daigaku Seimei Rikogakuin Seimei Rikogakukei, Institute of Science Tokyo, 4259 Nagatsuta-Cho Midzeori-Ku, Yokohama, 226-8501, Japan.
Chiral diaryl alcohols, such as (4-chlorophenyl)(pyridin-2-yl)methanol, are important intermediates for pharmaceutical synthesis. However, using alcohol dehydrogenases (ADHs) in the asymmetric reduction of diaryl ketones to produce the corresponding alcohols is challenging due to steric hindrance in the substrate binding pockets of the enzymes. In this study, the steric hindrance of the ADH from Geotrichum candidum NBRC 4597 (G.
View Article and Find Full Text PDFA Modified Green Star Area (MoGSA) and software to assess greenness of reactions in the chemistry laboratories.
PLoS One
December 2024
Department of Pharmaceutical of Chemistry, Faculty of Pharmacy, Kafrelsheikh University, Kafrelsheikh, Egypt.
The environmental and health impacts of chemical processes have been a growing concern, leading to the establishment of Green Chemistry principles. Introducing new metrics for the assessment of methods' greenness is crucial to evaluate the exerted efforts to conserve the environment. In this work, we introduce a Modified Green Star Area (MoGSA) and software to assess the greenness of chemical reactions in laboratory settings.
View Article and Find Full Text PDFPickering Emulsion Promoted Interfacial Sequential Chemo-Biocatalytic Reaction for the Synthesis of Chiral Alcohols from Styrene.
ACS Appl Mater Interfaces
October 2024
College of Biotechnology and Bioengineering, Zhejiang University of Technology, 310014 Hangzhou, China.
Chemo-biocatalytic cascades have emerged as a promising approach in the realm of advanced synthesis. However, reconciling the incompatible reaction conditions among distinct catalytic species presents a significant challenge. Herein, we introduce an innovative solution using an emulsion system stabilized by Janus silica nanoparticles, which serve as a bridge for both chemo-catalysts and biocatalysts at the interface.
View Article and Find Full Text PDFThe bacterial quorum sensing signal 2'-aminoacetophenone rewires immune cell bioenergetics through the Ppargc1a/Esrra axis to mediate tolerance to infection.
Elife
September 2024
Department of Surgery, Massachusetts General Hospital, and Harvard Medical School, Boston, United States.
How bacterial pathogens exploit host metabolism to promote immune tolerance and persist in infected hosts remains elusive. To achieve this, we show that () a recalcitrant pathogen, utilizes the quorum sensing (QS) signal 2'-aminoacetophenone (2-AA). Here, we unveil how 2-AA-driven immune tolerization causes distinct metabolic perturbations in murine macrophages' mitochondrial respiration and bioenergetics.
View Article and Find Full Text PDFApocynin alleviates thioacetamide-induced acute liver injury: Role of NOX1/NOX4/NF-κB/NLRP3 pathways.
Cytokine
November 2024
Department of Pharmacology and Toxicology, Faculty of Pharmacy, Mansoura University, Mansoura, Egypt.
The liver has a distinctive capacity to regenerate, yet severe acute injury can be life-threatening if not treated appropriately. Inflammation and oxidative stress are central processes implicated in the pathophysiology of acute livery injury. NOX isoforms are important enzymes for ROS generation, NF-κB and NLRP3 activation, its inhibition could be vital in alleviating acute liver injury (ALI).
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!