Iron-mediated cleavage of C-C bonds in vicinal tricarbonyl compounds in water.
Three of a kind: Vicinal tricarbonyl compounds undergo C-C cleavage mediated by ferric ions (see scheme). The observed cleavage of ninhydrin and dehydroascorbic acid has relevance for amino acid detection and the metabolism of vitamin C.
Mecinović
Jasmin
J
Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, United Kingdom.
Hamed
Refaat B
RB
Schofield
Christopher J
CJ
D000596:Amino Acids / Q000032:analysis; D001205:Ascorbic Acid / Q000737:chemistry / Q000378:metabolism; D002244:Carbon / Q000737:chemistry; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D003683:Dehydroascorbic Acid / Q000737:chemistry; D007501:Iron / Q000737:chemistry*; D009555:Ninhydrin / Q000737:chemistry; D014867:Water / Q000737:chemistry
D000596:Amino Acids; D002254:Carbonates; D014867:Water; D002244:Carbon; D007501:Iron; D009555:Ninhydrin; D001205:Ascorbic Acid; D003683:Dehydroascorbic Acid