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Environ Sci Technol

Title:		Secondary organic aerosol-forming reactions of glyoxal with amino acids
Author(s):		De Haan DO; Corrigan AL; Smith KW; Stroik DR; Turley JJ; Lee FE; Tolbert MA; Jimenez JL; Cordova KE; Ferrell GR;
Address:		"Department of Chemistry and Biochemistry, University of San Diego, 5998 Alcala Park, San Diego California 92110, USA. ddehaan@sandiego.edu"
Journal Title:		Environ Sci Technol
Year:		2009
Volume:		43
Issue:		8
Page Number:		2818 - 2824
DOI:		10.1021/es803534f
ISSN/ISBN:		0013-936X (Print) 0013-936X (Linking)
Abstract:		"Glyoxal, the simplest and most abundant alpha-dicarbonyl compound in the atmosphere, is scavenged by clouds and aerosol, where it reacts with nucleophiles to form low-volatility products. Here we examine the reactions of glyoxal with five amino acids common in clouds. When glyoxal and glycine, serine, aspartic acid or ornithine are present at concentrations as low as 30/microM in evaporating aqueous droplets or bulk solutions, 1,3-disubstituted imidazoles are formed in irreversible second-order reactions detected by nuclear magnetic resonance (NMR), aerosol mass spectrometry (AMS) and electrospray ionization mass spectrometry (ESI-MS). In contrast, glyoxal reacts with arginine preferentially at side chain amino groups, forming nonaromatic five-membered rings. All reactions were accompanied by browning. The uptake of 45 ppb glyoxal by solid-phase glycine aerosol at 50% RH was also studied and found to cause particle growth and the production of imidazole measured by scanning mobility particle sizing and AMS, respectively, with a glyoxal uptake coefficient alpha = 0.0004. Comparison of reaction kinetics in bulk and in drying droplets shows that conversion of glyoxal dihydrate to monohydrate accelerates the reaction by over 3 orders of magnitude, allowing these reactions to occur at atmospheric conditions"
Keywords:		"Aerosols/*chemistry Amino Acids/*chemistry Glyoxal/*chemistry Magnetic Resonance Spectroscopy Organic Chemicals/*chemistry Spectrometry, Mass, Electrospray Ionization Spectroscopy, Fourier Transform Infrared;"
Notes:		"MedlineDe Haan, David O Corrigan, Ashley L Smith, Kyle W Stroik, Daniel R Turley, Jacob J Lee, Frances E Tolbert, Margaret A Jimenez, Jose L Cordova, Kyle E Ferrell, Grant R eng Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S. 2009/05/30 Environ Sci Technol. 2009 Apr 15; 43(8):2818-24. doi: 10.1021/es803534f"