Squaric acid as a new chemoselective moiety for mass spectrometry-based metabolomics analysis of amines

Abstract

The investigation of microbiome-derived metabolites is important to understand metabolic interactions with their human host. New methodologies for mass spectrometric discovery of undetected metabolites with unknown bioactivity are required. Herein,...

Profiling of Amino Metabolites in Biological Samples without Protein Precipitation Using a Solid-Phase-Supported Phenyl Isothiocyanate-Based Chemoselective Probe

“…Globisch et al applied magnetic beads to the synthesis of chemoselective probes, which improved the separation efficiency and detection of new metabolites. 19,20,22,51,52 But, these commercialized magnetic beads have relatively lower capacity and are expensive, leading to an increase in the cost of analysis. In addition, the cleavage condition requires the addition of Pd(OAc) 2 , PPh 3 , and dimethylbarbituric acid, which introduce new impurities.…”

“…The introduction of magnetic materials further facilitates the purification process. Active ester and squaric acid were linked to magnetic beads for analysis of amino compounds in biological samples. − Hydroxylamine and hydrazide groups modified on magnetic particles were applied to capture carbonyl metabolites with improved coverage and sensitivity. , The emergence of these probes provides models for future research. However, in the above probes, the efficiency is not satisfied for the reduced reactivity between the solid and liquid phases.…”

Chemoselective bicyclobutane-based mass spectrometric detection of biological thiols uncovers human and bacterial metabolites

“…40 Immobilized probe A also contains the bioorthogonal cleavage site p-nitrocinnamyloxy-carbonyl (Noc / ) that can be cleaved under mild conditions using Pd(0) without altering the structure of the captured metabolites. [41][42][43][44] These two moieties are connected via a benzoylated diethylenetriamine linker (). 40 Our advanced probe design allows for the efficient magnetic separation of captured metabolites from the sample matrix as demonstrated for amine and carbonyl analysis.…”

“…40 Our advanced probe design allows for the efficient magnetic separation of captured metabolites from the sample matrix as demonstrated for amine and carbonyl analysis. 40,43,44 The incorporated BCB moiety was utilized to capture thiols by incubating biological samples with the activated probe. After separation from the matrix, the captured metabolites were released from the magnetic beads under mild conditions (Fig.…”

Catch-enrich-release approach for amine-containing natural products

“…[21][22][23][24][25] This concept is based on a selective catching via a derivatisation agent 25,26 attached to a solid support and the release of the (un)derivatised NPs triggered by an external stimulus. 27 Currently, several methods have been developed for the catch and release of NPs possessing amine, [28][29][30][31][32] hydroxy, [33][34][35][36] carbonyl, 28,29,[37][38][39][40] carboxylic acid, 28,29,34 thiol, 28,29,41 and alkyne 42,43 functional groups. Only a few strategies afforded an underivatized NP as the released compound by using siloxyl-functionalized resin [33][34][35][36] or by utilizing a pyridyl disulfide activation group.…”