What Factors Affect the Regioselectivity of Oxidation by Cytochrome P450? A DFT Study of Allylic Hydroxylation and Double Bond Epoxidation in a Model Reaction

2002 ◽  
Vol 124 (39) ◽  
pp. 11809-11826 ◽  
Author(s):  
Sam P. de Visser ◽  
François Ogliaro ◽  
Pankaz K. Sharma ◽  
Sason Shaik
Keyword(s):  
Cytochrome P450 ◽  
Double Bond ◽  
Model Reaction ◽  
Dft Study ◽  
Allylic Hydroxylation

scholarly journals Design of New Schiff-Base Copper(II) Complexes: Synthesis, Crystal Structures, DFT Study, and Binding Potency toward Cytochrome P450 3A4

ACS Omega ◽  
2021 ◽  
Author(s):  
Tunde L. Yusuf ◽  
Segun D. Oladipo ◽  
Sizwe Zamisa ◽  
Hezekiel M. Kumalo ◽  
Isiaka A. Lawal ◽  
...  
Keyword(s):  
Cytochrome P450 ◽  
Schiff Base ◽  
Crystal Structures ◽  
Dft Study ◽  
Cytochrome P450 3A4

scholarly journals Oxepinamide F biosynthesis involves enzymatic d-aminoacyl epimerization, 3H-oxepin formation, and hydroxylation induced double bond migration

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Liujuan Zheng ◽  
Haowen Wang ◽  
Aili Fan ◽  
Shu-Ming Li
Keyword(s):  
Cytochrome P450 ◽  
Double Bond ◽  
Biosynthetic Pathway ◽  
Hydroxyl Group ◽  
Cytochrome P450 Enzyme ◽  
Double Bond Migration ◽  
Feeding Experiments ◽  
Aspergillus Ustus ◽  
P450 Enzyme ◽  
Derivatives Of

Abstract Oxepinamides are derivatives of anthranilyl-containing tripeptides and share an oxepin ring and a fused pyrimidinone moiety. To the best of our knowledge, no studies have been reported on the elucidation of an oxepinamide biosynthetic pathway and conversion of a quinazolinone to a pyrimidinone-fused 1H-oxepin framework by a cytochrome P450 enzyme in fungal natural product biosynthesis. Here we report the isolation of oxepinamide F from Aspergillus ustus and identification of its biosynthetic pathway by gene deletion, heterologous expression, feeding experiments, and enzyme assays. The nonribosomal peptide synthase (NRPS) OpaA assembles the quinazolinone core with d-Phe incorporation. The cytochrome P450 enzyme OpaB catalyzes alone the oxepin ring formation. The flavoenzyme OpaC installs subsequently one hydroxyl group at the oxepin ring, accompanied by double bond migration. The epimerase OpaE changes the d-Phe residue back to l-form, which is essential for the final methylation by OpaF.

Structure sensitivity of double bond isomerization of butene over MgO surfaces: A periodic DFT study

2011 ◽  
Vol 974 (1-3) ◽  
pp. 52-56 ◽  
Author(s):  
Chuan-Ming Wang ◽  
Yang-Dong Wang ◽  
Jing Dong ◽  
Su Liu ◽  
Zai-Ku Xie
Keyword(s):  
Double Bond ◽  
Structure Sensitivity ◽  
Dft Study ◽  
Double Bond Isomerization ◽  
Periodic Dft

Metal-Free Addition of Boronic Acids to Silylnitronates

Synlett ◽  
2020 ◽  
Vol 31 (09) ◽  
pp. 856-860
Author(s):  
Laurent El Kaïm ◽  
Mansour Dolé Kerim ◽  
Pakoupati Boyode ◽  
Julian Garrec
Keyword(s):  
Reaction Mechanism ◽  
Double Bond ◽  
Boronic Acids ◽  
Dft Study ◽  
Metal Free ◽  
Nitro Derivatives ◽  
Oxime Derivatives ◽  
Nitrogen Double Bond ◽  
First Time ◽  
Aryl Transfer

We report for the first time a metal-free addition of boronic acids to silylnitronates to afford oxime derivatives through aryl transfer on the carbon nitrogen double bond. A reaction mechanism has been proposed in relation with a DFT study on the key aryl transfer. This arylation process is effective for cycloalkenyl nitro derivatives leading to oximes that may be oxidatively converted into 3-arylisoxazole derivatives.

scholarly journals A DFT Study of the Heme Role in the N-Demethylation of Theophylline Mediated by Compound I of Cytochrome P450

2007 ◽  
Vol 48 (4) ◽  
pp. 730-734 ◽  
Author(s):  
Mohamed Ismael ◽  
Carlos A. Del Carpio ◽  
Abdul Rajjak Shaikh ◽  
Hideyuki Tsuboi ◽  
Michihisa Koyama ◽  
...  
Keyword(s):  
Cytochrome P450 ◽  
Dft Study ◽  
Compound I

scholarly journals DFT Study on Double-bond Isomerization of trans-2-butene Catalyzed by Zeolites

2005 ◽  
Vol 21 (08) ◽  
pp. 898-902
Author(s):  
LI Hui-ying ◽  
◽  
PU Min ◽  
CHEN Biao-hua
Keyword(s):  
Double Bond ◽  
Dft Study ◽  
Double Bond Isomerization

Synthesis, X-ray, and DFT Study of the Double-Bond Pyramidalization in 1,7,8,9-Tetraphenyl-4,10,10- trimethyl-4-aza-10-silatricyclo[5.2.1.0.2,6]deca-8-ene-3,5-dione and Its Germanium Analogue

2006 ◽  
Vol 25 (1) ◽  
pp. 111-117 ◽  
Author(s):  
Davor Margetić ◽  
Yasujiro Murata ◽  
Koichi Komatsu ◽  
Mirjana Eckert-Maksić
Keyword(s):  
Double Bond ◽  
Dft Study ◽  
X Ray

Selective Allylic Hydroxylation of Octahydronaphthalene Derivatives with a Bridgehead Double Bond Using Electrochemical Method with Iron Picolinate Complexes.

ChemInform ◽  
2005 ◽  
Vol 36 (31) ◽  
Author(s):  
Iwao Okamoto ◽  
Wataru Funaki ◽  
Sachiyo Nobuchika ◽  
Mika Sawamura ◽  
Eiichi Kotani ◽  
...  
Keyword(s):  
Double Bond ◽  
Electrochemical Method ◽  
Iron Picolinate ◽  
Allylic Hydroxylation

Adsorption of 2-vinyl thiophene on Si(100)2 × 1: A van Der Waals corrected DFT study

2015 ◽  
Vol 14 (02) ◽  
pp. 1550011 ◽  
Author(s):  
Marilena Carbone
Keyword(s):  
Density Functional Theory ◽  
Double Bond ◽  
Aromatic Ring ◽  
Density Functional ◽  
Monomer Unit ◽  
Van Der Waals ◽  
Transition States ◽  
Dft Study ◽  
Functional Theory ◽  
Transition Energies

Oligo- and polythiophenes on surfaces play a fundamental role in building molecular circuits and organic-based electronics and may be assembled via interaction of the monomer units with the surface. In this framework, the nature of interaction of 2-vinyl thiophene (2VTP), a conjugated heteroaromatic monomer unit, with the Si (100) surface was studied by means of density functional theory (DFT). In particular, structural optimizations were performed comparing the effects of the inclusion of van der Waals (VdW) forces. It came out that the adsorption through the double bond is energetically favored, if VdW forces are included, whereas the adsorption through both aromatic ring and double bond simultaneously is more stable, if they are excluded. Physisorbed states were singled out and the barriers between two of them and the corresponding chemisorbed states were calculated along with the imaginary frequencies of the transition states. Also the transition energies have different values if the VdW forces are included.

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