Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Direct Carbon Isotope Exchange through Decarboxylative Carboxylation.

ABSTRACT: A two-step degradation-reconstruction approach to the carbon-14 radiolabeling of alkyl carboxylic acids is presented. Simple activation via redox-active ester formation was followed by nickel-mediated decarboxylative carboxylation to afford a range of complex compounds with ample isotopic incorporations for drug metabolism and pharmacokinetic studies. The practicality and operational simplicity of the protocol were demonstrated by its use in an industrial carbon-14 radiolabeling setting.

SUBMITTER: Kingston C

PROVIDER: S-EPMC7000106 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Direct Carbon Isotope Exchange through Decarboxylative Carboxylation.

Kingston Cian C Wallace Michael A MA Allentoff Alban J AJ deGruyter Justine N JN Chen Jason S JS Gong Sharon X SX Bonacorsi Samuel S Baran Phil S PS

Journal of the American Chemical Society 20190103 2

A two-step degradation-reconstruction approach to the carbon-14 radiolabeling of alkyl carboxylic acids is presented. Simple activation via redox-active ester formation was followed by nickel-mediated decarboxylative carboxylation to afford a range of complex compounds with ample isotopic incorporations for drug metabolism and pharmacokinetic studies. The practicality and operational simplicity of the protocol were demonstrated by its use in an industrial carbon-14 radiolabeling setting. ...[more]

PMID: 30605319

Similar Datasets

Transition-Metal-Free Carbon Isotope Exchange of Phenyl Acetic Acids.

Project description:A transition-metal-free carbon isotope exchange procedure on phenyl acetic acids is described. Utilizing the universal precursor CO2 , this protocol allows the carbon isotope to be inserted into the carboxylic acid position, with no need of precursor synthesis. This procedure enabled the labeling of 15 pharmaceuticals and was compatible with carbon isotopes [14 C] and [13 C]. A proof of concept with [11 C] was also obtained with low molar activity valuable for distribution studies.

| S-EPMC7496475 | biostudies-literature

Direct electrochemical defluorinative carboxylation of α-CF<sub>3</sub> alkenes with carbon dioxide.

Project description:An unprecedented γ-carboxylation of α-CF3 alkenes with CO2 is reported. This approach constitutes a rare example of using electrochemical methods to achieve regioselectivity complementary to conventional metal catalysis. Accordingly, using platinum plate as both a working cathode and a nonsacrificial anode in a user-friendly undivided cell under constant current conditions, the γ-carboxylation provides efficient access to vinylacetic acids bearing a gem-difluoroalkene moiety from a broad range of substrates. The synthetic utility is further demonstrated by gram-scale synthesis and elaboration to several value-added products. Cyclic voltammetry and density functional theory calculations were performed to provide mechanistic insights into the reaction.

| S-EPMC8162267 | biostudies-literature

Late-Stage Carbon-14 Labeling and Isotope Exchange: Emerging Opportunities and Future Challenges.

Project description:Carbon-14 (14C) is a gold standard technology routinely utilized in pharmaceutical and agrochemical industries for tracking synthetic organic molecules and providing their metabolic and safety profiles. While the state of the art has been dominated for decades by traditional multistep synthetic approaches, the recent emergence of late-stage carbon isotope labeling has provided new avenues to rapidly access carbon-14-labeled biologically relevant compounds. In particular, the development of carbon isotope exchange has represented a fundamental paradigm change, opening the way to unexplored synthetic transformations. In this Perspective, we discuss the recent developments in the field with a critical assessment of the literature. We subsequently discuss research directions and future challenges within this rapidly evolving field.

| S-EPMC9241029 | biostudies-literature

Visible-Light-Enabled Direct Decarboxylative N-Alkylation.

Project description:The development of efficient and selective C-N bond-forming reactions from abundant feedstock chemicals remains a central theme in organic chemistry owing to the key roles of amines in synthesis, drug discovery, and materials science. Herein, we present a dual catalytic system for the N-alkylation of diverse aromatic carbocyclic and heterocyclic amines directly with carboxylic acids, by-passing their preactivation as redox-active esters. The reaction, which is enabled by visible-light-driven, acridine-catalyzed decarboxylation, provides access to N-alkylated secondary and tertiary anilines and N-heterocycles. Additional examples, including double alkylation, the installation of metabolically robust deuterated methyl groups, and tandem ring formation, further demonstrate the potential of the direct decarboxylative alkylation (DDA) reaction.

| S-EPMC7200280 | biostudies-literature

Copper-Catalyzed Carboxylation of Aryl Iodides with Carbon Dioxide.

Project description:A method for carboxylation of aryl iodides with carbon dioxide has been developed. The reaction employs low loadings of copper iodide/TMEDA or DMEDA catalyst, 1 atm of CO2, DMSO or DMA solvent, and proceeds at 25-70 °C. Good functional group tolerance is observed, with ester, bromide, chloride, fluoride, ether, hydroxy, amino, and ketone functionalities tolerated. Additionally, hindered aryl iodides such as iodomesitylene can also be carboxylated.

| S-EPMC3839347 | biostudies-literature

Decarboxylative Peptide Macrocyclization through Photoredox Catalysis.

Project description:A method for the decarboxylative macrocyclization of peptides bearing N-terminal Michael acceptors has been developed. This synthetic method enables the efficient synthesis of cyclic peptides containing γ-amino acids and is tolerant of functionalities present in both natural and non-proteinogenic amino acids. Linear precursors ranging from 3 to 15 amino acids cyclize effectively under this photoredox method. To demonstrate the preparative utility of this method in the context of bioactive molecules, we synthesized COR-005, a somatostatin analogue that is currently in clinical trials.

| S-EPMC5225041 | biostudies-literature

Water Exchange Versus Carbon Dioxide for Colonoscopy

Project description:Colonoscopy is commonly used in screening for colorectal cancer. A refined technique of colonoscopy involving the use of water as the sole modality to aid colonoscope insertion, water exchange, has been described in recent research papers to decrease patient discomfort and pain, and to reduce the need for sedation during colonoscopy when compared with standard air insufflation. Carbon dioxide insufflation has been described to decrease patient discomfort after colonoscopy. No randomized trial has so far compared the use of water exchange to carbon dioxide insufflation. Our hypothesis is that water exchange inflicts less discomfort to patients undergoing colonoscopy than carbon dioxide insufflation. Patients undergoing screening colonoscopy in two centers in Norway, one center in Poland and one center in The Netherlands will be enrolled and randomized to examination of either of the two methods.

| 2128017 | ecrin-mdr-crc

Daylight-driven carbon exchange through a vertically structured microbial community

Project description:Tracing autotroph and heterotroph photosynthetic catalytic carbon cycling within a microbial mat, confirming biomass 13C incorporation into extracellular polymeric substances through proteomics.

2023-07-20 | PXD012190 | Pride

Carbon-11 carboxylation of trialkoxysilane and trimethylsilane derivatives using [11C]CO2.

Project description:A novel carboxylation radiosynthesis methodology is described starting from cyclotron-produced [11C]CO2 and fluoride-activated silane derivatives. Six carbon-11 labelled carboxylic acids were obtained from their corresponding trimethylsilyl and trialkoxysilyl precursors in a one-pot labelling methodology. The radiochemical yields ranged from 19% to 93% within 12 minutes post [11C]CO2 delivery with a trapping efficiency of 21-89%.

| S-EPMC7384297 | biostudies-literature

Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides.

Project description:Sulfonamides feature prominently in organic synthesis, materials science and medicinal chemistry, where they play important roles as bioisosteric replacements of carboxylic acids and other carbonyls. Yet, a general synthetic platform for the direct conversion of carboxylic acids to a range of functionalized sulfonamides has remained elusive. Herein, we present a visible light-induced, dual catalytic platform that for the first time allows for a one-step access to sulfonamides and sulfonyl azides directly from carboxylic acids. The broad scope of the direct decarboxylative amidosulfonation (DDAS) platform is enabled by the efficient direct conversion of carboxylic acids to sulfinic acids that is catalyzed by acridine photocatalysts and interfaced with copper-catalyzed sulfur-nitrogen bond-forming cross-couplings with both electrophilic and nucleophilic reagents.

| S-EPMC8115300 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data