Cargando…

The molecular mechanism of P450-catalyzed amination of the pyrrolidine derivative of lidocaine: insights from multiscale simulations

Nitrogen heterocycles are key and prevalent motifs in drugs. Evolved variants of cytochrome P450(BM3) (CYP102A1) from Bacillus megaterium employ high-valent oxo-iron(iv) species to catalyze the synthesis of imidazolidine-4-ones via an intramolecular C–H amination. Herein, we use multi-scale simulati...

Descripción completa

Detalles Bibliográficos
Autores principales:	Wang, Conger, Wu, Peng, Wang, Zhanfeng, Wang, Binju
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	The Royal Society of Chemistry 2021
Materias:	Chemistry
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9037892/ https://www.ncbi.nlm.nih.gov/pubmed/35480638 http://dx.doi.org/10.1039/d1ra04564d

Ejemplares similares

Palladium/GF-Phos-catalyzed asymmetric carbenylative amination to access chiral pyrrolidines and piperidines
por: Sun, Yue, et al.
Publicado: (2022)

Ligand-assisted palladium-catalyzed C–H alkenylation of aliphatic amines for the synthesis of functionalized pyrrolidines
por: He, Chuan, et al.
Publicado: (2017)

Exploring the Potential of Cytochrome P450 CYP109B1 Catalyzed Regio—and Stereoselective Steroid Hydroxylation
por: Zhang, Xiaodong, et al.
Publicado: (2021)

Palladium/Xu-Phos-catalyzed asymmetric carboamination towards isoxazolidines and pyrrolidines
por: Wang, Yuzhuo, et al.
Publicado: (2021)

Synthesis of heteroatom-containing pyrrolidine derivatives based on Ti(O-iPr)(4) and EtMgBr-catalyzed carbocyclization of allylpropargyl amines with Et(2)Zn
por: Kadikova, Rita N., et al.
Publicado: (2020)

MD simulations and QM/MM calculations show that single-site mutations of cytochrome P450(BM3) alter the active site’s complexity and the chemoselectivity of oxidation without changing the active species
por: Dubey, Kshatresh Dutta, et al.
Publicado: (2017)

Editorial: Molecular Dynamics Simulations of Metalloproteins and Metalloenzymes
por: Dubey, Kshatresh Dutta, et al.
Publicado: (2021)

Formal aromaticity transfer for palladium-catalyzed coupling between phenols and pyrrolidines/indolines
por: Qiu, Zihang, et al.
Publicado: (2017)

Catalytic asymmetric synthesis of enantioenriched α-deuterated pyrrolidine derivatives
por: Chang, Xin, et al.
Publicado: (2022)

Mechanistic Studies on the Synthesis of Pyrrolidines and Piperidines via Copper-Catalyzed Intramolecular C–H Amination
por: Muñoz-Molina, José María, et al.
Publicado: (2022)

Synthesis and molecular modeling studies of cholinesterase inhibitor dispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidines]
por: Youssef, M. Adel, et al.
Publicado: (2020)

From the bottle: simple iron salts for the efficient synthesis of pyrrolidines via catalytic C–H bond amination
por: Stroek, Wowa, et al.
Publicado: (2023)

Primary amines from lignocellulose by direct amination of alcohol intermediates, catalyzed by RANEY® Ni
por: Wu, Xianyuan, et al.
Publicado: (2022)

Automated MUltiscale simulation environment
por: Sabadell-Rendón, Albert, et al.
Publicado: (2023)

Pd-catalyzed access to mono- and di-fluoroallylic amines from primary anilines
por: Wang, Xingben, et al.
Publicado: (2022)

Calcium(ii)-catalyzed enantioselective conjugate additions of amines
por: Uno, Brice E., et al.
Publicado: (2018)

P450-BM3-Catalyzed Sulfoxidation versus Hydroxylation: A Common or Two Different Catalytically Active Species?
por: Wang, Jian-bo, et al.
Publicado: (2020)

Iron-catalyzed urea synthesis: dehydrogenative coupling of methanol and amines
por: Lane, Elizabeth M., et al.
Publicado: (2018)

Transfer hydrogenations catalyzed by streptavidin-hosted secondary amine organocatalysts
por: Santi, Nicolò, et al.
Publicado: (2021)

Ti-catalyzed ring-opening oxidative amination of methylenecyclopropanes with diazenes
por: Beaumier, Evan P., et al.
Publicado: (2020)

Computational insights into Ir(iii)-catalyzed allylic C–H amination of terminal alkenes: mechanism, regioselectivity, and catalytic activity
por: Pan, Deng, et al.
Publicado: (2021)

Graphene Oxide Catalyzed Synthesis of Fused Chromeno Spiro Pyrrolidine Oxindoles via Tandem Decarboxylation and 1,3-Dipolar Cycloaddition
por: Singh, Vipin, et al.
Publicado: (2022)

Pd-catalyzed [3 + 2] cycloaddition of cyclic ketimines and trimethylenemethanes toward N-fused pyrrolidines bearing a quaternary carbon
por: Choi, Seoung-Mi, et al.
Publicado: (2021)

A metal-catalyzed new approach for α-alkynylation of cyclic amines
por: Cui, Yifan, et al.
Publicado: (2018)

Asymmetric synthesis of primary amines catalyzed by thermotolerant fungal reductive aminases
por: Mangas-Sanchez, Juan, et al.
Publicado: (2020)

Construction of chiral α-tert-amine scaffolds via amine-catalyzed asymmetric Mannich reactions of alkyl-substituted ketimines
por: Homma, Chihiro, et al.
Publicado: (2020)

Mechanistic Features in Al(I)-Mediated Oxidative Addition of Aryl C–F Bonds: Insights From Density Functional Theory Calculations
por: Zhang, Xiangfei, et al.
Publicado: (2019)

Multiscale numerical simulation of in-plane mechanical properties of two-dimensional monolayers
por: Imani Yengejeh, Sadegh, et al.
Publicado: (2021)

Transient directing group enabled Pd-catalyzed C–H oxygenation of benzaldehydes and benzylic amines
por: Tian, Mixiang, et al.
Publicado: (2022)

Simulation of self-heating process on the nanoscale: a multiscale approach for molecular models of nanocomposite materials
por: Donati, Greta, et al.
Publicado: (2020)

Cobalt catalyzed sp(3) C–H amination utilizing aryl azides
por: Villanueva, Omar, et al.
Publicado: (2015)

Towards a general ruthenium-catalyzed hydrogenation of secondary and tertiary amides to amines
por: Cabrero-Antonino, Jose R., et al.
Publicado: (2016)

Stereoretentive and regioselective selenium-catalyzed intermolecular propargylic C–H amination of alkynes
por: Maloney, T. Parker, et al.
Publicado: (2022)

P450-Catalyzed Intramolecular sp(3) C–H Amination with Arylsulfonyl Azide Substrates
por: Singh, Ritesh, et al.
Publicado: (2014)

Enzymatic C(sp(3))-H Amination: P450-Catalyzed Conversion of Carbonazidates into Oxazolidinones
por: Singh, Ritesh, et al.
Publicado: (2015)

Conformational Change of H64 and Substrate Transportation: Insight Into a Full Picture of Enzymatic Hydration of CO(2) by Carbonic Anhydrase
por: Fu, Yuzhuang, et al.
Publicado: (2021)

Enantioselective construction of C-chiral allylic sulfilimines via the iridium-catalyzed allylic amination with S,S-diphenylsulfilimine: asymmetric synthesis of primary allylic amines
por: Grange, Rebecca L., et al.
Publicado: (2015)

A modular and divergent approach to spirocyclic pyrrolidines
por: Shennan, Benjamin D. A., et al.
Publicado: (2020)

An efficient nickel/silver co-catalyzed remote C–H amination of 8-aminoquinolines with azodicarboxylates at room temperature
por: Zhao, Ruinan, et al.
Publicado: (2018)

Microwave-assisted synthesis of 7-azaindoles via iron-catalyzed cyclization of an o-haloaromatic amine with terminal alkynes
por: Le, Yi, et al.
Publicado: (2019)

Cannot write session to /tmp/vufind_sessions/sess_9savp8qg1169t3v92hq57l11uc