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Structural elucidation of isocyanate-peptide adducts using tandem mass spectrometry.

Authors
Hettick-JM; Ruwona-TB; Siegel-PD
Source
J Am Soc Mass Spectrom 2009 Aug; 20(8):1567-1575
NIOSHTIC No.
20035683
Abstract
Diisocyanates are highly reactive chemical compounds widely used in the manufacture of polyurethanes. Although diisocyanates have been identified as causative agents of allergic respiratory diseases, the specific mechanism by which these diseases occur is largely unknown. To better understand the chemical species produced when isocyanates are reacted with model peptides, tandem mass spectrometry was employed to unambiguously identify the binding site of four commercially-relevant isocyanates on model peptides. In each case, the isocyanates react preferentially with the N-terminus of the peptide. No evidence of side-chain/ isocyanate adduct formation exclusive of the N-terminus was observed. However, significant intra-molecular diisocyanate crosslinking was observed between the N-terminal amine and a side-chain amine of arginine, when Arg was located within two residues of the N-terminus. Addition of multiple isocyanates to the peptide occurs via polymerization of the isocyanate at the N-terminus, rather than via addition of multiple isocyanate molecules to varied residues within the peptide. The direct observation of isocyanate binding to the N-terminus of peptides under these experimental conditions is in good agreement with previous studies on the relative reaction rate of isocyanate with amino acid functional groups.
Keywords
Mass-spectrometry; Analytical-processes; Analytical-instruments; Isocyanates; Allergic-reactions; Respiratory-system-disorders; Respiratory-hypersensitivity
Contact
Dr. J. M. Hettick, Centers for Disease Control and Prevention, National Institute for Occupational Safety and Health, Health Effects Laboratory Division, MS L-2040, 1095 Willowdale Road, Morgantown, WV 26505, USA
CODEN
JAMSEF
Publication Date
20090801
Document Type
Journal Article
Email Address
jhettick@cdc.gov
Fiscal Year
2009
NTIS Accession No.
NTIS Price
Issue of Publication
8
ISSN
1044-0305
NIOSH Division
HELD
Source Name
Journal of the American Society for Mass Spectrometry
State
WV
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