Formation and cleavage of C–C bonds by enzymatic oxidation–reduction reactions

FP Guengerich, FK Yoshimoto - Chemical Reviews, 2018 - ACS Publications
Many oxidation–reduction (redox) enzymes, particularly oxygenases, have roles in reactions
that make and break C–C bonds. The list includes cytochrome P450 and other heme-based …

Aromatase: contributions to physiology and disease in women and men

J Blakemore, F Naftolin - Physiology, 2016 - journals.physiology.org
Abstract Aromatase (estrogen synthetase; EC 1.14. 14.1) catalyzes the demethylation of
androgens' carbon 19, producing phenolic 18-carbon estrogens. Aromatase is most widely …

Mechanisms of cytochrome P450-catalyzed oxidations

FP Guengerich - ACS catalysis, 2018 - ACS Publications
Enzymes are complex biological catalysts and are critical to life. Most oxidations of
chemicals are catalyzed by cytochrome P450 (P450, CYP) enzymes, which generally utilize …

Substrate oxidation by cytochrome P450 enzymes

PR Ortiz de Montellano - Cytochrome P450: structure, mechanism, and …, 2015 - Springer
Cytochrome P450 enzymes catalyze a broad diversity of reactions, including well-
established transformations such as carbon and nitrogen hydroxylation, heteroatom …

Non-P450 drug-metabolizing enzymes: contribution to drug disposition, toxicity, and development

T Fukami, T Yokoi, M Nakajima - Annual Review of …, 2022 - annualreviews.org
Most clinically used drugs are metabolized in the body via oxidation, reduction, or hydrolysis
reactions, which are considered phase I reactions. Cytochrome P450 (P450) enzymes …

From alkyl halides to ketones: nickel‐catalyzed reductive carbonylation utilizing ethyl chloroformate as the carbonyl source

R Shi, X Hu - Angewandte Chemie International Edition, 2019 - Wiley Online Library
Ketones are an important class of molecules in synthetic and medicinal chemistry. Rapid
and modular synthesis of ketones remains in high demand. Described here is a nickel …

Rhodium (III)-Catalyzed Oxidative C–H Alkylation of Aniline Derivatives with Allylic Alcohols To Produce β-Aryl Ketones

SM Khake, N Chatani - ACS Catalysis, 2022 - ACS Publications
The Rh (III)-catalyzed C–H oxidative alkylation of aniline derivatives with readily available
secondary allyl alcohols using a pyrimidine-directing group, leading to the production of β …

Oxygen-18 Labeling Defines a Ferric Peroxide (Compound 0) Mechanism in the Oxidative Deformylation of Aldehydes by Cytochrome P450 2B4

Y Tateishi, KD McCarty, MV Martin… - ACS catalysis, 2024 - ACS Publications
Most cytochrome P450 (P450) oxidations are considered to occur with the active oxidant
being a perferryl oxygen (FeO3+, Compound I). However, a ferric peroxide (FeO2̅ …

Rhodium-catalyzed C–H alkylation of indolines with allylic alcohols: direct access to β-aryl carbonyl compounds

SH Han, M Choi, T Jeong, S Sharma… - The Journal of …, 2015 - ACS Publications
The rhodium (III)-catalyzed site-selective C–H alkylation of various N-heterocycles, such as
indolines, carbazoles, and pyrroles with readily available allylic alcohols is described. This …

Practical Catalytic Cleavage of C(sp3)−C(sp3) Bonds in Amines

W Li, W Liu, DK Leonard, J Rabeah… - Angewandte …, 2019 - Wiley Online Library
The selective cleavage of thermodynamically stable C (sp3)− C (sp3) single bonds is rare
compared to their ubiquitous formation. Herein, we describe a general methodology for such …