Aldehyde detection by chromogenic/fluorogenic oxime bond fragmentation.
Amination of 4-nitrophenol, umbelliferone and 4-methylumbelliferone gave the corresponding oxyamines 1-3. These oxyamines react with aldehydes and ketones to form oximes. In the case of aliphatic aldehydes and electron-poor aromatic aldehydes, the oximes undergo base-catalyzed fragmentation in aqueous buffer in the presence of bovine serum albumin to give the parent phenols, which is the acyclic analog of Kemp's elimination reaction of 5-nitrobenzisoxazole 28. The process can be used as a spectrophotometric assay for formaldehyde under aqueous neutral conditions.
Salahuddin
Syed
S
Department of Chemistry & Biochemistry, University of Bern, Freiestrasse 3, 3012 Bern, Switzerland.
Renaudet
Olivier
O
Reymond
Jean-Louis
JL
D000447:Aldehydes / Q000032:analysis* / Q000737:chemistry; D000586:Amination; D002855:Chromatography, Thin Layer; D002863:Chromogenic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry / Q000378:metabolism; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D005557:Formaldehyde / Q000032:analysis / Q000737:chemistry / Q000378:metabolism; D006923:Hymecromone / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D007700:Kinetics; D008071:Lipoprotein Lipase / Q000737:chemistry / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009596:Nitrophenols / Q000737:chemistry; D010091:Oximes / Q000138:chemical synthesis / Q000737:chemistry*; D011549:Pseudomonas / Q000201:enzymology; D012710:Serum Albumin, Bovine / Q000737:chemistry; D013053:Spectrophotometry; D014468:Umbelliferones / Q000737:chemistry
D000447:Aldehydes; D002863:Chromogenic Compounds; D004987:Ethers; D005456:Fluorescent Dyes; D007659:Ketones; D009596:Nitrophenols; D010091:Oximes; D014468:Umbelliferones; D005557:Formaldehyde; D012710:Serum Albumin, Bovine; D006923:Hymecromone; C031477:7-hydroxycoumarin; D008071:Lipoprotein Lipase; C024836:4-nitrophenol