Direct Carbon Isotope Exchange through Decarboxylative Carboxylation.

J Am Chem Soc

Department of Chemistry , The Scripps Research Institute, 10550 North Torrey Pines Road , La Jolla , California 92037 , United States.

Published: January 2019

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.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7000106PMC
http://dx.doi.org/10.1021/jacs.8b12035DOI Listing

Publication Analysis

Top Keywords

decarboxylative carboxylation
8
carbon-14 radiolabeling
8
direct carbon
4
carbon isotope
4
isotope exchange
4
exchange decarboxylative
4
carboxylation two-step
4
two-step degradation-reconstruction
4
degradation-reconstruction approach
4
approach carbon-14
4

Similar Publications

-Butyl hypochlorite was employed as a versatile reagent for chlorooxidation of indoles, chlorination of 2-oxindoles, and decarboxylative chlorination of the indole-2-carboxylic acids. Four types of products including 2-chloro-3-oxindoles, 2,2-dichloro-3-oxindoles, 3,3-dichloro-2-oxindoles, and 2,3-dichloroindoles could be selectively obtained in moderate to excellent yields by switching the substrates. Various synthetically useful functional groups, such as halogen atoms, cyano, nitro, and methoxycarbonyl groups, remain intact during the reactions.

View Article and Find Full Text PDF

Amino alcohols are vital in natural products, pharmaceuticals and agrochemicals, and as key building blocks for various applications. Traditional synthesis methods often rely on polar bond retrosynthetic analysis, requiring extensive protecting group manipulations that complicate direct access. Here we show a streamlined approach using a serine-derived chiral carboxylic acid in stereoselective electrocatalytic decarboxylative transformations, enabling efficient access to enantiopure amino alcohols.

View Article and Find Full Text PDF

Iron-Photocatalyzed Decarboxylative Alkylation of Carboxylic Acids with Morita-Baylis-Hillman Acetates.

Org Lett

January 2025

College of Advanced Interdisciplinary Science and Technology (CAIST), Henan University of Technology, Zhengzhou 450001, Henan, P. R. China.

We present an iron-photocatalyzed decarboxylative alkylation strategy involving carboxylic acids and Morita-Baylis-Hillman (MBH) acetates to synthesize -type tri- and tetrasubstituted alkenes with moderate to excellent stereoselectivity (/ ratio up to >19:1). This method is applicable to a broad range of structurally diverse primary, secondary, and tertiary alkyl carboxylic acids, as well as complex pharmaceutical and natural carboxylic acids, achieving efficient alkylation of various MBH acetates under mild conditions (>60 examples, with yields up to 96%). This approach offers a powerful strategy for streamlined alkylation.

View Article and Find Full Text PDF

The algal macrolide goniodomin A (GDA) undergoes ring-cleavage under unusually mild, alkaline conditions to form mixtures of stereoisomers of seco acids GDA-sa and iso-GDA-sa. In the primary fragmentation pathway, opening of the macrolide ring occurs by displacement of the carboxyl group by a base-catalyzed attack of the C32 hemiketal hydroxy group on C31, yielding an oxirane-carboxylic acid, named goniodomic acid. The oxirane ring is unstable, undergoing solvolytic opening to form mainly GDA-sa.

View Article and Find Full Text PDF

Expression, purification and characterization of a dual function α-dioxygenase/peroxidase from Mycolicibacterium smegmatis.

Biochim Biophys Acta Mol Cell Biol Lipids

December 2024

Department of Chemistry and Biochemistry, Villanova University, Villanova, PA 19085, USA. Electronic address:

An open reading frame from the actinobacterium Mycolicibacterium smegmatis annotated as a Prostaglandin H Synthase (PGHS) was expressed with an N-terminal (his) tag and purified to homogeneity. The enzyme has a monomeric molecular weight of 68.3 kD and exists as a dimer in the presence of nonionic detergent.

View Article and Find Full Text PDF

Want 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!