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http://dx.doi.org/10.5012/bkcs.2009.30.11.2542

Influence of the Structural Characteristics of Amino Acids on Direct Methylation Behaviors by TMAH in Pyrolysis  

Choi, Sung-Seen (Department of Chemistry, Sejong University)
Ko, Ji-Eun (Department of Chemistry, Sejong University)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.11, 2009 , pp. 2542-2548 More about this Journal
Abstract
Direct methylation behaviors of 20 amino acids with tetramethylammonium hydroxide (TMAH) were studied under diluted conditions with silica. Amino acid concentration was controlled by dilution with silica ($SiO_2$) and the molar ratios of amino acid/silica were 0.20, 0.50, and 2.0. The molar ratios of amino acid/TMAH (0.51 - 4.64) also varied. It was found that arginine, asparagine, aspartic acid, cysteine, glutamic acid, and glutamine did not generate any directly methylated pyrolysis products, whereas alanine, glycine, isoleucine, leucine, methionine, phenylanaline, valine, and proline generated all the directly methylated pyrolysis products. Tri- and tetra methylated products of lysine consisted of two types. Histidine and threonine hardly generated the partly methylated products. Mono- and dimethylated products of serine, tryptophan, and tyrosine were not observed. Relative intensities of the methylated products varied with the amino acid concentration, TMAH concentration, and pyrolysis temperature. Direct methylation behaviors of amino acids were explained by the structural characteristics of amino acids.
Keywords
Amino acids; Direct methylation; TMAH; Py-GC/MS; Silica;
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Times Cited By Web Of Science : 3  (Related Records In Web of Science)
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1 Moldoveanu, S. C. Analytical Pyrolysis of Natural Organic Polymers Techniques and Instrumentation in Analytical Chemistry, Vol. 20; Elsevier: Amsterdam, 1998
2 Schulten, H. R.; Gleixner, G. Water Res. 1999, 33, 2489-2498   DOI   ScienceOn
3 Koo, J.; Park, C. H.; Han, C.; Na, Y. C. Bull. Kor. Chem. Soc. 2009, 30, 368-372   DOI   ScienceOn
4 Ratcliff, M. A.; Medley, E. E.; Simmonds, P. G. J. Org. Chem. 1974, 39, 1481-1490   DOI
5 Chiavari, G.; Galletti, G. C. J. Anal. Appl. Pyrolysis 1992, 24, 123-137   DOI   ScienceOn
6 Stankiewicz, B. A.; van Bergen, P. F.; Duncan, I. J.; Carter, J. F.; Briggs, D. E. G.; Evershed, R. P. Rapid Commun. Mass Spectrom. 1996, 10, 1747-1757   DOI   ScienceOn
7 Basiuk, V. A.; Navarro-Gonzalez, R.; Basiuk, E. V. J. Anal. Appl. Pyrolysis 1998, 45, 89-102   DOI   ScienceOn
8 Lehtonen, T.; Peuravuori, J.; Pihlaja, K. J. Anal. Appl. Pyrolysis 2003, 68/69, 315-329   DOI   ScienceOn
9 Joll, C. A.; Huynh, T.; Heitzet, A. J. Anal. Appl. Pyrolysis 2003, 70, 151-167   DOI   ScienceOn
10 Voorhees, K. J.; Basile, F.; Beverly, M. B.; Abbas-Hawks, C.; Hendricker, A.; Cody, R. B.; Hadfield, T. L. J. Anal. Appl. Pyrolysis 1997, 40/41, 111-134   DOI   ScienceOn
11 Abbas-Hawks, C.; Voorhees, K. J.; Hadfield, T. L. Rapid Commun. Mass Spectrom. 1996, 10, 1802-1806   DOI   ScienceOn
12 Zang, X.; van Heemst, J. D. H.; Dna, K. J.; Hatcher, P. G. Org. Geochem. 2000, 31, 679-695   DOI   ScienceOn
13 Knicker, H.; Hatcher, P. G. Naturwissenschaften 1997, 84, 231-234   DOI   ScienceOn
14 Gallois, N.; Templier, J.; Derenne, S. J. Anal. Appl. Pyrolysis 2007, 80, 216-230   DOI   ScienceOn
15 Hendricker, A. D.; Voorhees, K. J. J. Anal. Appl. Pyrolysis 1998, 48, 17-33   DOI   ScienceOn
16 Choi, S.-S.; Choi, S.-J. Bull. Kor. Chem. Soc. 2006, 27, 1473   DOI   ScienceOn
17 Kuroda, K.; Inoue, Y.; Sakai, K. J. Anal. Appl. Pyrolysis 1990, 18, 59-69   DOI   ScienceOn
18 Nist standard reference database number 69, http://webbook.nist.gov/chemistry/
19 Zang, X.; Brown, J. C.; van Heemst, J. D. H.; Palumbo, A.; Hatcheret, P. G. J. Anal. Appl. Pyrolysis 2001, 61, 181-193   DOI   ScienceOn
20 Challinor, J. M. J. Anal. Appl. Pyrolysis 1989, 16, 323-333   DOI   ScienceOn
21 Wolff, S.; Wang, M.-J. Rubber Chem. Technol. 1992, 65, 329   DOI
22 Ou, Y.-C.; Yu, Z.-Z.; Vidal, A.; Donnet, J. B. Rubber Chem. Technol. 1994, 67, 834   DOI   ScienceOn
23 Byers, J. T. Rubber World 1998, 218(6), 38