Analytical TMAH pyrolysis of dipeptides: Formation of new complex cyclic compounds related to the presence of the peptide bond

Journal of Analytical and Applied Pyrolysis

Volumn 104, Issue , 2013, Pages 684-694

  Templier, J ^a   Gallois, N ^a   Derenne, S ^a  

^a UPMC University Paris 06   (France)

Author keywords

Diketopiperazines; Dipeptide; GC MS; Imidazolidinones; Peptide bond; TMAH pyrolysis

Indexed keywords

ALKYLATION; AMINO ACIDS; CHAINS; PYROLYSIS;

DI-PEPTIDES; DIKETOPIPERAZINES; GC/MS; IMIDAZOLIDINONES; PEPTIDE BONDS;

PEPTIDES;

EID: 84887997305     PISSN: 01652370     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jaap.2013.09.017     Document Type: Article

References (31)

1. B.A. Stankiewicz, and P.F. van Bergen Nitrogen-containing macromolecules in the bio- and geosphere: an introduction ACS Symp. Ser. 707 1998 1 12
2. H. Knicker, M.W.I. Schmidt, and I. Kögel-Knabner Nature of organic nitrogen in fine particle size separates of sandy soils of highly industrialized areas as revealed by NMR spectroscopy Soil Biol. Biochem. 32 2000 241 252
3. 13C nuclear magnetic resonance spectroscopy in the structural characterisation of humic acids Anal. Chim. Acta 424 2000 243 255
4. 15N NMR Pedosphere 11 2001 151 157
5. 15N NMR spectroscopic study on nitrogen forms in humic substances of soils Pedosphere 11 2001 1 9
6. D.P. Dick, C. Nunes Gonçalves, R.S.D. Dalmolin, H. Knicker, E. Klamt, I. Kögel-Knabner, M.L. Simões, and L. Martin-Neto Characteristics of soil organic matter of different Brazilian Ferralsols under native vegetation as a function of soil depth Geoderma 124 2005 319 333
7. 15N cross polarization/magic angle spinning nuclear magnetic resonance spectroscopy Org. Geochem. 36 2005 1490 1497
8. R.T. Nguyen, and H.R. Harvey Preservation of protein in marine systems: hydrophobic and other noncovalent associations as major stabilizing forces Geochim. Cosmochim. Acta 65 2001 1467 1480
9. R.T. Nguyen, and H.R. Harvey Preservation via macromolecular associations during Botryococcus braunii decay: proteins in the Pula kerogen Org. Geochem. 34 2003 1391 1403
10. A. Garcette-Lepecq, S. Derenne, C. Largeau, I. Bouloubassi, and A. Saliot Origin and formation pathways of kerogen-like organic matter in recent sediments off the Danube delta (northwestern Black Sea) Org. Geochem. 31 2000 1663 1683
11. H. Knicker, J.C. del Río, P.G. Hatcher, and R.D. Minard Identification of protein remnants in insoluble geo-polymers by using TMAH thermochemolysis/GC-MS Org. Geochem. 32 2001 397 409
12. 13C NMR spectroscopy study Geochim. Cosmochim. Acta 65 2001 3299 3305
13. A. Riboulleau, T. Mongenot, F. Baudin, S. Derenne, and C. Largeau Factors controlling the survival of proteinaceous material in Late Tithonian kerogens (Kashpir Oil Shales, Russia) Org. Geochem. 33 2002 1127 1130
14. J.C. del Río, M.A. Olivella, H. Knicker, and F.X.C. de las Heras Preservation of peptide moieties in three Spanish sulfur-rich tertiary kerogens Org. Geochem. 35 2004 993 999
15. J.B. Reeves III, and B.A. Francis Pyrolysis-gas chromatography for the analysis of proteins: with emphasis on forages ACS Symp. Ser. 707 1998 47 62
16. J.W. de Leeuw, and M. Baas The behavior of esters in the presence of tetramethylammonium salts at elevated temperatures: flash pyrolysis or flash chemolysis? J. Anal. Appl. Pyrol. 26 1993 175 184
17. K.J. Voorhees, F. Basile, M.B. Beverly, C. Abbas-Hawks, A.D. Hendricker, R.B. Cody, and T.L. Hadfeld The use of biomarker compounds for the identification of bacteria by pyrolysis-mass spectrometry J. Anal. Appl. Pyrol. 40/41 1997 111 134
18. A.D. Hendricker, and K.J. Voorhees Amino acid and oligopeptide analysis using Curie-point pyrolysis mass spectrometry with in-situ thermal hydrolysis and methylation: mechanistic considerations J. Anal. Appl. Pyrol. 48 1998 17 33
19. A. Mannino, and H.R. Harvey Terrigenous dissolved organic matter along an estuarine gradient and its flux to the coastal ocean Org. Geochem. 31 2000 1611 1625
20. N. Gallois, J. Templier, and S. Derenne Pyrolysis-gas chromatography-mass spectrometry of the 20 protein amino acids in the presence of TMAH J. Anal. Appl. Pyrol. 80 2007 216 230
21. J. Li, Z. Wang, X. Yang, L. Hu, Y. Liu, and C. Wang Evaluation of the pyrolysis pathway of glycine and glycylglycine by TG-FTIR J. Anal. Appl. Pyrol. 80 2007 247 253
22. D. Fabbri, A. Adamiano, G. Falini, R. De Marco, and I. Mancini Analytical pyrolysis of dipeptides containing proline and amino acids with polar side chains. Novel 2,5-diketopiperazine markers in the pyrolysates of proteins J. Anal. Appl. Pyrol. 95 2012 145 155
23. V.A. Basiuk, and J. Douda Pyrolysis of poly-glycine and poly-l-alanine: analysis of less-volatile products by gas chromatography/Fourier transform infrared spectroscopy/mass spectrometry J. Anal. Appl. Pyrol. 55 2000 235 246
24. J.P. Dworzanski, A. Tripathi, A.P. Snyder, W.M. Maswdeh, and C.H. Wick Novel biomarkers for Gram-type differentiation of bacteria by pyrolysis-gas chromatography-mass spectrometry J. Anal. Appl. Pyrol. 73 2005 29 38
25. A.D. Hendricker, and K.J. Voorhees An investigation into the Curie-point pyrolysis-mass spectrometry of glycyl dipeptides J. Anal. Appl. Pyrol. 36 1996 51 70
26. A.S. Noguerola, B. Murugaverl, and K.J. Voorhees An investigation of dipeptides containing polar and nonpolar side groups by Curie-point pyrolysis tandem mass spectrometry J. Am. Soc. Mass Spectrom. 3 1992 750 756
27. G.C. Galletti, G. Chiavari, and P. Bocchini Thermal decomposition products of aspartame as determined by pyrolysis-gas chromatography/mass spectrometry J. Anal. Appl. Pyrol. 32 1995 137 151
28. J.M. Challinor The scope of pyrolysis methylation reactions J. Anal. Appl. Pyrol. 20 1991 15 24
29. N. Gallois, J. Templier, and S. Derenne Limitations in interpreting TMAH thermochemolysis of natural organic matter via consideration of glycine and alanine derivatives Org. Geochem. 41 2010 1338 1340
30. T.H. Lowry, and K.S. Richardson Mechanism and Theory in Organic Chemistry 1981 Harper and Row Publishers New York 291
31. V.A. Basiuk, and R. Navarro-Gonzalez. Identification of hexahydroimidazo[1,2-a]pyrazine-3,6-diones and hexahydroimidazo[1,2-a]imidazo[1, 2-d]pyrazine-3,8-diones, unusual products of silica-catalyzed amino acid thermal condensation and products of their thermal decomposition using coupled high-performance liquid chromatography-particle beam mass spectrometry and gas chromatography-Fourier transform infrared spectroscopy-mass spectrometry J. Chromatogr. A 776 1997 255 273