Abstract Reactive carbonyl compounds are common pollutants and endogenous metabolites that are often toxic at high concentrations. Removal/detoxification of carbonyl compounds requires selective small molecule scavengers; however, few molecules suitable for this task have been fully characterised. Here, we report NMR-based kinetic and selectivity studies on representative 1-amino-but-3-enes, which are reported to be selective formaldehyde scavengers. Our experiments reveal that 1-amino-but-3-enes containing phenyl groups at position 1 react with formaldehyde via a 2-aza-Cope rearrangement. However, they also react with other carbonyl compounds, including the biologically relevant 1,2-dicarbonyl compound glyoxylic acid. The most efficient and promiscuous scavenging compound promoted the growth of Escherichia coli cells, while studies on cell lysate revealed potential for aldehyde sequestration. Overall, our analyses suggest that 1-amino-but-3-enes can be used to scavenge a variety of toxic carbonyl compounds and may be used in imaging and quantification studies, as well as for biomedical applications.
Bulman et al. (Mon,) studied this question.