# 1-Amino-but-3-enes scavenge formaldehyde and glyoxylic acid

## TL;DR

Scientists found that 1-amino-but-3-enes can detoxify harmful carbonyl compounds like formaldehyde and glyoxylic acid, opening possibilities for biomedical use.

## Contribution

The study reveals that 1-amino-but-3-enes with phenyl groups effectively scavenge formaldehyde and glyoxylic acid through specific chemical reactions.

## Key findings

- 1-amino-but-3-enes with phenyl groups react with formaldehyde via a 2-aza-Cope rearrangement.
- These compounds also scavenge glyoxylic acid and promote Escherichia coli cell growth.
- Cell lysate studies suggest potential for aldehyde sequestration and biomedical applications.

## 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.

Reactive carbonyl compounds pose toxicity challenges as pollutants and metabolites; however, synthetic scavengers for detoxification remain underdeveloped. Here, the authors demonstrate that 1-amino-but-3-enes, particularly those with phenyl groups, selectively scavenge formaldehyde and glyoxylic acid, offering potential for biomedical applications.