365-69-5

Upstream product

• 1544-46-3 2-fluoroacetaldehyde 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 
• 89426-34-6 4-fluoro-L-threonine 

Relevant academic research and scientific papers

Defluorination of 4-fluorothreonine by threonine deaminase

4-Fluorothreonine (4-FT) is the only naturally occurring fluorinated amino acid antibiotic. Although two conserved proteins in the 4-FT pathway have been found to be involved in self-detoxification mechanisms, the 4-FT-producing strains may also require an alternative pathway to degrade the intracellular 4-FT. In this study, we examined the possible degradation role of three enzymes involved in threonine metabolite pathways toward 4-FT as a possible degradation route to avoid in vivo 4-FT accumulation. Among these three enzymes, threonine deaminase was found to catalyse a defluorination reaction to generate 4-hydroxy-α-ketobutyrate, which is supposed to be further metabolised by an aldolase that likely is a unique occurrence in the 4-FT-producing strains. Our finding may constitute a 4-FT degradation pathway as a complementary resistance mechanism.

Automation of [18F]fluoroacetaldehyde synthesis: application to a recombinant human interleukin-1 receptor antagonist (rhIL-1RA)

[18F]Fluoroacetaldehyde is a biocompatible prosthetic group that has been implemented pre-clinically using a semi-automated remotely controlled system. Automation of radiosyntheses permits use of higher levels of [18F]fluoride whilst

Synthesis of [18F]fluoroacetaldehyde. Application to [ 18F]fluoroethylation of benzylamine under reductive alkylation conditions

The radiosynthesis of a new [18F]fluoroalkylating agent, [ 18F]fluoroacetaldehyde, is described. It was produced using the Kornblum method by oxidation with dimethyl sulphoxide of 2-[18F] fluoroethyl p-toluenesulphonate ([18F]FETos). In these conditions the oxidation proceeds smoothly and rapidly to the selective conversion of tosyl esters of primary alcohols to aldehydes with no carboxylic acids being produced. The chemical identity of [18F]fluoroacetaldehyde was determined by comparing its chromatographic properties as well as those of its 2,4-dinitrophenylhydrazone (2,4-DNPH) derivative with those of, respectively, the standard fluoroacetaldehyde and its 2,4-DNPH derivative. Standard fluoroacetaldehyde was prepared by oxidation of fluoroethanol with pyridinium dichromate and characterized as its 2,4-DNPH derivative by mass spectrometry. To test its reactivity with amines under reductive alkylation conditions, [ 18F]fluoroacetaldehyde was reacted with benzylamine used as model substrate. The chemical identity of the resulting radiolabeled product was determined to be [18F]N-(2-fluoroethyl)-benzylamine by comparing its chromatographic properties with those of the synthesized standard N-(2-fluoroethyl)-benzylamine characterized by 19F and 1H NMR spectroscopy and mass spectrometry. This new fluorine-18 labelled synthon may find applications in radiolabelling peptide, protein and antibody fragments as well as in aldol condensation or in the Mannich reaction. Copyright