Gas chromatographic determination and mechanism of formation of D-amino acids occurring in fermented and roasted cocoa beans, cocoa powder, chocolate and cocoa shell

Amino Acids

Volumn 31, Issue 1, 2006, Pages 63-72

  Patzold R ^a   Bruckner H ^a  

^a JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

Amadori rearrangement products; Amino acid enantiomers; Chirasil Val; Gas chromatography mass spectrometry; Maillard reaction; Racemization; Theobroma cacao L.

Indexed keywords

ASPARAGINE DERIVATIVE; ASPARTIC ACID DERIVATIVE; DEXTRO ALANINE; DEXTRO AMINO ACID; DEXTRO LEUCINE; DEXTRO PHENYLALANINE; DEXTRO PROLINE; DEXTRO SERINE; DEXTRO TYROSINE; DEXTRO VALINE; ESTER DERIVATIVE; FAT; FRUCTOSE; FRUCTOSE DEXTRO PHENYLALANINE; FRUCTOSE PHENYLALANINE; ISOLEUCINE; PHENYLALANINE; PHENYLALANINE DERIVATIVE; PROLINE DERIVATIVE; PROTEIN; TYROSINE DERIVATIVE; UNCLASSIFIED DRUG; VOLATILE AGENT;

AMADORI REARRANGEMENT; AMINO ACID ANALYSIS; AMINO ACID SYNTHESIS; ANALYTICAL EQUIPMENT; ARTICLE; BEAN; CACAO; CATION EXCHANGE; COOKING; COTE D'IVOIRE; ENANTIOSELECTIVITY; FERMENTATION; FOOD ANALYSIS; GAS CHROMATOGRAPHY; GHANA; GLYCATION; HEATING; INDONESIA; ISOLATION PROCEDURE; MASS SPECTROMETRY; POWDER; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; RACEMIZATION; TEMPERATURE SENSITIVITY;

AMINO ACIDS; CACAO; FERMENTATION; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; MOLECULAR STRUCTURE; SENSITIVITY AND SPECIFICITY; STEREOISOMERISM;

THEOBROMA CACAO;

EID: 33746145164     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-006-0330-1     Document Type: Article

References (37)

1. Ali H, Pätzold R, Brückner H (2006) Determination of L- and D-amino acids in smokeless tobacco products and tobacco. Food Chem (in press) (DOI 10.1016/j.food.chem.2005.08.056)
2. B Biehl G Ziegleder EH Meursing K van de Zaan 1993 Cocoa R Macrae RK Robinson MJ Sadler Encyclopedia of food science and technology and nutrition Academic Press London 1073 1097
3. H Brückner D Becker M Lüpke 1993 Chirality of amino acids of microorganisms used in food technology Chirality 5 385 392
4. H Brückner M Hausch 1990 D-amino acids as ubiquitous constituents in fermented foods G Lubec GA Rosenthal Amino acids: Chemistry, biology and medicine Escom Leiden 1127 1182
5. H Brückner J Justus J Kirschbaum 2001 Saccharide induced racemization of amino acids in the course of the Maillard reaction Amino Acids 21 429 433
6. Brückner H, Kirschbaum J, Pätzold R (2002) A new racemization mechanism for amino acids. In: Benedetti E, Pedone C (eds) Peptides 2002, Proceedings of the Twenty-Seventh European Peptide Symposium, August 31-September 6, 2002, Sorrento. Edizione Ziino, Napoli, Italy, pp 54-55
7. H Brückner T Westhauser 2003 Chromatographic determination of L- and D-amino acids in plants Amino Acids 24 43 55
8. ES de Brito NHP Garcia MI Gallao AL Cortelazzo PS Fevereiro MR Braga 2000 Structural and chemical changes in cocoa (Theobroma cacao L) during fermentation, drying and roasting J Sci Food Agric 81 281 288
9. K Eichner M Karel 1972 Influence of water content and water activity on the sugar-amino browning reaction in model systems under various conditions J Agric Food Chem 20 218 223
10. K Eichner M Ciner-Doruk 1979 Bildung von Amadori-Verbindungen in wasserarmen Modellsystemen Z Lebensm Unters Forsch 168 360 367
11. T Erbe H Brückner 2000 Chromatographic determination of amino acid enantiomers in beers and raw materials used for their manufacture J Chromatogr A 881 81 91
12. H Frank G Nicholson E Bayer 1978 Chiral polysiloxanes for resolution of optical antipodes Angew Chem Int Ed 17 363 365
13. M Friedman 1996 Food browning and its prevention: an overview J Agric Food Chem 44 631 653
14. M Friedman PM Masters 1982 Kinetics of racemization of amino acid residues in casein J Food Sci 47 760 764
15. M Heinzler K Eichner 1991a Verhalten von Amadori-Verbindungen während der Kakaoverarbeitung. 1. Bildung und Abbau von Amadori-Verbindungen Z Lebensm Unters Forsch 192 445 450
16. M Heinzler K Eichner 1991b Verhalten von Amadori-Verbindungen während der Kakaoverarbeitung. 2. Bildung von Aromastoffen unter Röstbedingungen Z Lebensm Unters Forsch 192 24 29
17. WJ Hurst RA Martin 1980 Use of o-phthalaldehyde derivatives and high-pressure liquid chromatography in determining the free amino acids in cocoa beans J Agric Food Chem 28 1039
18. P-M Kirchhoff B Biehl H Ziegeler-Berghausen M Hammoor R Lieberei 1989 Kinetics of the formation of free amino acids in cocoa seeds during fermentation Food Chem 34 161 179
19. J Kleinert 1997 Handbuch der Kakaoverarbeitung und Schokoladeherstellung Behr's Verlag Hamburg
20. F Ledl E Schleicher 1990 New aspects of the Maillard reaction in foods and in the human body Angew Chem Int Edit 29 565 594
21. RA Martin 1987 Chocolate Adv Food Res 31 211 342
22. M Moll B Gross 1981 Isolation and purification of Amadori compounds by semipreparative reversed phase high performance liquid chromatography J Chromatogr 206 186 192
23. S Oberparleiter G Ziegleder 1997 Amadoriverbindungen als Aromavorstufen in Kakao Nahrung 41 142 145
24. JO Offem 1990 Individual variation in the amino acid and chemical composition of defatted cocoa bean meal of three varieties of cocoa (Theobroma cacao) from South Eastern Nigeria J Sci Food Agric 52 129 135
25. R Pätzold H Brückner 2005a Aminosäureenantiomere in Kakao und Kakaoprodukten als Parameter für die Röstungsintensität Proc Germ Nutr Soc 7 83 84
26. R Pätzold H Brückner 2005b Chiral separation of amino acids by gas chromatography I Molnár-Perl Journal of chromatograph library, Vol. 70: Quantitation of amino acids and amines by chromatography, methods and protocols Elsevier Amsterdam 98 118
27. R Pätzold H Brückner 2005c Gas chromatographic quantification of free D-amino acids in higher vertebrates Biomed Chromatogr 19 466 473
28. R Pätzold H Brückner 2005d Mass spectrometric detection and formation of D-amino acids in processed plant saps, syrups, and fruit juice concentrates J Agric Food Chem 53 9722 9729
29. Pätzold R, Brückner H (2006) Gas chromatographic detection of D-amino acids in natural and thermally treated bee honeys and studies on the mechanism of their formation as result of the Maillard reaction. Eur Food Res Technol (in press). DOI 10.1007/s00217-005-0211-y
30. Pätzold R, Brückner H (2004a) Studies on the racemization (epimerization) of amino acids and peptides in the course of the Maillard reaction. In: Flegel M, Fridkin M, Gilon C, Slaninová J (eds) Peptides 2004, Proceedings of the Third International and Twenty-Eighth European Peptide Symposium, September 5-10, 2004, Prague, Czech Republic. Kenes International, Geneva, Switzerland, pp 997-998
31. R Pätzold H Brückner 2004b Mechanistische Aspekte und Konsequenzen der Bildung von D-Aminosäuren im Laufe der Maillardreaktion Lebensmittelchemie 58 100
32. R Pätzold N Kutz H Brückner 2005 Determination of D-amino acids in cocoa beans (Theobroma cacao L.) and cocoa products Amino Acids 29 64
33. R Pätzold Rodriguez Nieto H Brückner 2003 Chiral gas chromatographic analysis of amino acids in fortified wines Chromatographia [Suppl] 57 S207 S211
34. H Puziah S Jinap SKS Muhammad A Asbi 1998 Changes in free amino acid, peptide-N, sugar and pyrazine concentration during cocoa fermentation J Sci Food Agric 78 535 542
35. Schieberle P (2000) The chemistry and technology of cocoa. In: Caffeinated beverages. ACS Symposium Series 754: 262-275
36. R Schnee K Eichner 1987 Analytische Bestimmung des Röstgrades von Kakao Z Lebensm Unters Forsch 185 188 194
37. VA Yaylayan A Huyghues-Despointes 1994 Chemistry of Amadori rearrangement products: analysis, synthesis, kinetics, reactions and spectroscopic properties Crit Rev Food Sci 34 321 369