Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 58, Issue 24, Pages 12761-12768Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf103251w
Keywords
Diacetyl; 2,3-butanedione; artificial butter flavoring; arginine adducts; toxicity
Funding
- Intramural NIH HHS [ZIA ES101865-06] Funding Source: Medline
- NIEHS NIH HHS [N01ES75563] Funding Source: Medline
- PHS HHS [HHSN29120077563] Funding Source: Medline
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The butter flavorant diacetyl (2,3-butanedione) is implicated in causing obliterative bronchiolitis in microwave popcorn plant workers. Because diacetyl modifies arginine residues, an immunological basis for its toxicity is under investigation. Reaction products of diacetyl with N-alpha-acetylarginine (AcArg) were determined as a model for hapten formation, with characterization by mass spectrometry, NMR, and HPLC with UV detection and radiodetection. Four products were identified by LC-MS, each with a positive ion of m/z 303 (diacetyl + AcArg); one pair displayed an additional ion at m/z 217 (AcArg), the other pair at m/z 285 (- H(2)O). Their (1)H-(13)C NMR correlation spectra were consistent with the addition of one or two of the guanidine nitrogens to form aminols. Open-chain pairs interconverted at pH 2, as did the cyclized, but all four interconverted at neutral pH. This is the first structural characterization of the covalent adducts between diacetyl and an arginine moiety.
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