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Journal of Atmospheric Chemistry

, Volume 63, Issue 3, pp 187–202 | Cite as

Chemical transformations of peptide containing fine particles: oxidative processing, accretion reactions and implications to the atmospheric fate of cell-derived materials in organic aerosol

  • Scott Geddes
  • James Zahardis
  • Giuseppe A. PetrucciEmail author
Article

Abstract

The atmospheric processing by ozone of peptide-containing mixed particles was investigated as proxies for biogenic and sea spray primary organic aerosol. Reactions were performed in a flow reactor and particle composition was monitored by photoelectron resonance capture ionization aerosol mass spectrometry. Mixed particles containing dipeptides in a saturated organic matrix of stearic and palmitic acids showed no reaction under ozonolysis at exposure levels of 2.5 × 10−4 atm s O3. However reactions of mixed particles of a dipeptide (Leu-Leu) in an unsaturated matrix (oleic acid) under the same conditions resulted in a rapid loss of the peptide ion signal, as well as the carrier matrix, and appearance of a number of ion signals corresponding to secondary products. High molecular weight imides and amides have been identified corresponding to possible reactions of ozonolysis products and reactive intermediates (i.e. aldehydes, stabilized Criegee intermediates). Additionally, tautomerisation of the imides to enamines in the particle phase is postulated, with ozonolysis of the enamine followed by regioselective decomposition of the primary ozonide to form an amide whereby the peptide incorporates an aldehydic group at the N-terminus. The same general reactivity pattern was observed for mixed particles of diglycine and oleic acid. This behavior was not observed in solution phase experiments, where the tautomerisation favors the more stable imine form, indicating that particulate phase reactions of this nature may be dependent on the specific particle physical properties. The implications of this chemistry with respect the atmospheric aging of cell-derived organic aerosol are discussed.

Keywords

Ozonolysis Bioaerosol Proteinaceous particles Organic aerosol Soft ionization aerosol mass spectrometry PERCI 

Notes

Acknowledgements

Funding for this research was provided by the National Science Foundation (AGS ATM-0925052) and the UVM Transportation Research Center. The authors also gratefully acknowledge support from the National Science Foundation for purchase of the LC-MS (CHE MRI-0821501) as well as Dr. S. Flemer for synthesis of the dipeptides.

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Copyright information

© Springer Science+Business Media B.V. 2010

Authors and Affiliations

  • Scott Geddes
    • 1
  • James Zahardis
    • 1
  • Giuseppe A. Petrucci
    • 1
    Email author
  1. 1.Department of ChemistryUniversity of VermontBurlingtonUSA

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