1,8-diazafluorenone and related compounds. A new reagent for the detection of (α-amino acids and latent fingerprints.

✍ Scribed by Ronald Grigg; Theeravat Mongkolaussavaratana; C. Anthony Pounds; Sasikala Sivagnanam

• Publisher: Elsevier Science
• Year: 1990
• Tongue: French
• Weight: 227 KB
• Volume: 31
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)97283-6

✦ Synopsis

Diazafluorenone (DFO) reacts with a-amino acids and their esters via imine formation to give decarboxylated azomethine ylides and ester substituted azomethine ylides respectively.

In the presence of N-methylmaleimide these azomethine ylides undergo stereospecific cycloaddition via endotransition states. Analogues of DFO give similar cycloadducts.

In the absence of dipolarophiles the aamino acids and DFO give a red fluorescent dye thus providing a sensitive method for detecting latent fingerprints on paper. The detection and quantitation of a-amino acids plays a central role in peptide and protein chemistry and has led to the development of a number of reagents that react with a-amino acids to produce coloured and/or fluorescent species. Typical reagents include dansyl chloride,' fluorescamine,' 4-chloro-7nitrobenzofuran (NBD-Cl),3 o-phthalaldehyde,4 and ninhydrin and its' benzo analogues.5