Synthetic methodologies in organic chemistry involving incorporation of [17O] and [18O] isotopes

What is it about?

This review is a critical survey of the literature on chemical synthesis of labeled organic compounds that highlights the most significant developments on synthetic strategies involving stable oxygen isotopes ([17O] and [18O]). The labeling methodologies are categorized in groups, according to the oxygen-containing functional group. Among them, are the hydroxyl of alcohols and phenols, the carbonyl function in aldehydes and ketones, and the carboxyl group of the carboxylic acids. Moreover, other oxygen-containing functionalities are derivatives of the aforementioned compounds, such as ethers, esters, amides, acid halides, anhydrides, and, in addition, phosphates, phosphonates, sulfonates, sulfones, and nitro and nitroso compounds. Oxygen-containing functional groups occupy a key position both at the structural and physiological level in all biologically important molecules, such as proteins, nucleic acids, carbohydrates, and phospholipids. There are many successful applications of these labeling-based methodologies and the potential for the discovery of additional useful reactions and biosynthetic ways to introduce [17/18O] labels selectively to organic molecules of mechanistic, biological, and technological importance.

Featured Image