Cost-efficient and user-friendly ¹⁷O/¹⁸O labeling procedures of fatty acids using mechanochemistry

Abstract

Two mechanochemical procedures for 17O/18O-isotope labeling of fatty acids are reported: a carboxylic acid activation/hydrolysis approach and a saponification approach.

First direct insight into the local environment and dynamics of water molecules in the whewellite mineral phase: mechanochemical isotopic enrichment and high-resolution 17O and 2H NMR analyses

“…91 Here, enriched water was actually used to play the role of both a liquid grinding assistant and a reagent to introduce the isotopic label, in line with our previous work on isotopic labeling using ball-milling. [61][62][63][64][65][66] Three different experimental conditions were compared for the deuteration of COM. The first experiment adopted a very gentle approach: shaking without a milling ball, allowing the reagents to be mixed at the frequency of 25 Hz for 5 minutes (COM-SHAKE-2 H), and without any risk of affecting the crystallinity of the COM starting material.…”

“…Building upon our recent demonstration that mechanochemistry can be a very powerful technique for enriching in 17 O various inorganic materials [61][62][63][64] and organic molecules. 63,65,66 Here, we will demonstrate for the first time that ball-milling methods are also very well suited for the 17 O-labeling or deuteration of hydrated biomimetic minerals like hydrated calcium oxalates.…”

First direct insight into the local environment and dynamics of water molecules in the whewellite mineral phase: mechanochemical isotopic enrichment and high-resolution 17O and 2H NMR analyses

“…81 Here, enriched water was actually used to play the role of both a liquid grinding assistant and a reagent to introduce the isotopic label, in line with our previous work on isotopic labeling using ball-milling. [54][55][56][57][58][59] Three different experimental conditions were compared for the deuteration of COM. The first experiment adopted a very gentle approach: shaking without a milling ball, allowing the reagents to be mixed at the frequency of 25 Hz for 5 minutes (COM-SHAKE-2 H), and without any risk of affecting the crystallinity of the COM starting material.…”

“…Building upon our recent demonstration that mechanochemistry can be a very powerful technique for enriching in 17 O various inorganic materials [54][55][56][57] and organic molecules. 56,58,59 Here, we will demonstrate for the first time that ball-milling methods are also very well suited for the 17 O-labeling or deuteration of hydrated biomimetic minerals like hydrated calcium oxalates.…”

Operando acoustic analysis: a valuable method for investigating reaction mechanisms in mechanochemistry

“…Finally, in order to demonstrate the utility of sound measurements for the optimization of ball-milling reaction conditions, we decided to study the hydrolysis of an activated fatty acid, lauric acid, using this operando method. Indeed, during our previous work on the 17 O/ 18 O isotopic enrichment of fatty acids, 31,32 we had found that for saturated fatty acids, the hydrolysis time of the activated acyl-imidazole intermediates had to be systematically optimized by repeating the experiments with various milling times. Given that this hydrolysis is accompanied by a change in texture of the reaction medium, which switches from a powdery aspect to a more oily one, we suspected that acoustic measurements could be used to determine the time aer which the hydrolysis is complete (Fig.…”