메뉴 건너뛰기




Volumn 36, Issue 3, 2009, Pages 465-474

Enolization and racemization reactions of glucose and fructose on heating with amino-acid enantiomers and the formation of melanoidins as a result of the Maillard reaction

Author keywords

Enolization; Extinction coefficient; Maillard reaction; Melanoidins; Racemization

Indexed keywords

ALANINE DERIVATIVE; ASPARAGINE; FRUCTOSE; GLUCOSE; MARFEY REAGENT; MELANOIDINE; POLYMER; SUGAR; UNCLASSIFIED DRUG;

EID: 67349179653     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-008-0104-z     Document Type: Article
Times cited : (30)

References (53)
  • 2
    • 0001536872 scopus 로고
    • 3-deoxyglycosuloses (3-deoxyglycosones) and the degradation of carbohydrates
    • EFLJ Anet 1964 3-deoxyglycosuloses (3-deoxyglycosones) and the degradation of carbohydrates Adv Carbohydr Chem 19 181 218
    • (1964) Adv Carbohydr Chem , vol.19 , pp. 181-218
    • Eflj, A.1
  • 3
    • 0015520435 scopus 로고
    • Kinetics of racemization of amino acids as a function of pH
    • JL Bada 1972 Kinetics of racemization of amino acids as a function of pH J Am Chem Soc 94 1371 1373
    • (1972) J Am Chem Soc , vol.94 , pp. 1371-1373
    • Bada, J.L.1
  • 4
    • 0000611410 scopus 로고
    • Degradation of lactose during heating of milk. I. Reaction pathways
    • HE Berg MAJS Van Boekel 1994 Degradation of lactose during heating of milk. I. Reaction pathways Neth Milk Dairy J 48 157 175
    • (1994) Neth Milk Dairy J , vol.48 , pp. 157-175
    • Berg, H.E.1    Van Boekel Majs2
  • 5
    • 12144268411 scopus 로고    scopus 로고
    • Marfey's reagent for chiral amino acid analysis: A review
    • DOI 10.1007/s00726-004-0118-0
    • R Bhushan H Brückner 2004 Marfey's reagent for chiral amino acid analysis: a review Amino Acids 27 231 247 (Pubitemid 40110064)
    • (2004) Amino Acids , vol.27 , Issue.3-4 , pp. 231-247
    • Bhushan, R.1    Bruckner, H.2
  • 6
    • 0030931762 scopus 로고    scopus 로고
    • Direct resolution of enantiomers by impregnated TLC
    • DOI 10.1002/(SICI)1099-0801(199709)11:5<280::AID-BMC697>3.0.CO;2-U
    • R Bhushan J Martens 1997 Direct resolution of enantiomers by impregnated TLC Biomed Chromatogr 11 280 285 (Pubitemid 27410159)
    • (1997) Biomedical Chromatography , vol.11 , Issue.5 , pp. 280-285
    • Bhushan, R.1    Martens, J.2
  • 9
    • 0035659569 scopus 로고    scopus 로고
    • Saccharide induced racemization of amino acids in the course of the maillard reaction
    • DOI 10.1007/s007260170007
    • 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 (Pubitemid 34025171)
    • (2001) Amino Acids , vol.21 , Issue.4 , pp. 429-433
    • Bruckner, H.1    Justus, J.2    Kirschbaum, J.3
  • 10
    • 18944382257 scopus 로고    scopus 로고
    • Determination of free D-amino acids in mammalian by chiral gas chromatography-mass spectrometry
    • H Brückner A Schieber 2000 Determination of free D-amino acids in mammalian by chiral gas chromatography-mass spectrometry J High Resol Chromatogr 23 576 582
    • (2000) J High Resol Chromatogr , vol.23 , pp. 576-582
    • Brückner, H.1    Schieber, A.2
  • 11
    • 4444269425 scopus 로고    scopus 로고
    • Roast effects on coffee amino acid enantiomers
    • DOI 10.1016/j.foodchem.2004.02.039, PII S0308814604002043
    • S Casal E Mendes MBPP Oliveira MA Ferreira 2005 Roast effects on coffee amino acid enantiomers Food Chem 89 333 340 (Pubitemid 39195103)
    • (2005) Food Chemistry , vol.89 , Issue.3 , pp. 333-340
    • Casal, S.1    Mendes, E.2    Oliveira, M.B.P.P.3    Ferreira, M.A.4
  • 12
    • 14644438531 scopus 로고    scopus 로고
    • Unravelling the contribution of melanoidins to the antioxidant activity of coffee brews
    • C Delgado-Andrade FJ Morales 2005 Unravelling the contribution of melanoidins to the antioxidant activity of coffee brews J Agric Food Chem 53 1403 1407
    • (2005) J Agric Food Chem , vol.53 , pp. 1403-1407
    • Delgado-Andrade, C.1    Morales, F.J.2
  • 13
    • 0343729876 scopus 로고    scopus 로고
    • Chromatographic determination of amino acid enantiomers in beers and raw materials used for their manufacture
    • DOI 10.1016/S0021-9673(00)00255-7, PII S0021967300002557
    • T Erbe H Brückner 2000 Chromatographic determination of amino acids enantiomers in beers and raw materials used for their manufacture J Chromatogr A 881 81 91 (Pubitemid 30332195)
    • (2000) Journal of Chromatography A , vol.881 , Issue.1-2 , pp. 81-91
    • Erbe, T.1    Bruckner, H.2
  • 14
    • 0002674537 scopus 로고    scopus 로고
    • Studies on the optical isomerization of dietary amino acids in vinegar and aqueous acetic acid
    • T Erbe H Brückner 2000 Studies on the optical isomerization of dietary amino acids in vinegar and aqueous acetic acid Eur Food Res Technol 21 6 12
    • (2000) Eur Food Res Technol , vol.21 , pp. 6-12
    • Erbe, T.1    Brückner, H.2
  • 17
    • 0032839957 scopus 로고    scopus 로고
    • Chemistry, nutrition, and microbiology of D-amino acids
    • DOI 10.1021/jf990080u
    • M Friedman 1999 Chemistry, nutrition, and microbiology of D-amino acids J Agric Food Chem 47 3457 3479 (Pubitemid 29449456)
    • (1999) Journal of Agricultural and Food Chemistry , vol.47 , Issue.9 , pp. 3457-3479
    • Friedman, M.1
  • 19
    • 0039108306 scopus 로고    scopus 로고
    • A study of sugar colourants through ion exchange and salt regeneration
    • C Guimaraes LSM Bento M Mota 1996 A study of sugar colourants through ion exchange and salt regeneration Int Sugar J 98 584 587 (Pubitemid 126353685)
    • (1996) International Sugar Journal , vol.98 , Issue.1175 , pp. 584-587
    • Guimaraes, C.1    Bento, L.S.M.2    Mota, M.3
  • 20
    • 0001540734 scopus 로고
    • The browning reaction of Amadori compounds derived from various sugars
    • H Hashiba 1982 The browning reaction of Amadori compounds derived from various sugars Agric Biol Chem 46 547 548
    • (1982) Agric Biol Chem , vol.46 , pp. 547-548
    • Hashiba, H.1
  • 21
    • 0001489984 scopus 로고    scopus 로고
    • Studies on the Relationship between Molecular Weight and the Color Potency of Fractions Obtained by Thermal Treatment of Glucose/Amino Acid and Glucose/Protein Solutions by Using Ultracentrifugation and Color Dilution Techniques
    • T Hofmann 1998 Studies on the relationship between molecular weight and the color potency of fractions obtained by thermal treatment of glucose/amino acid and glucose/protein solutions by using ultracentifugation and color dilution techniques J Agric Food Chem 46 3891 3895 (Pubitemid 128488466)
    • (1998) Journal of Agricultural and Food Chemistry , vol.46 , Issue.10 , pp. 3891-3895
    • Hofmann, T.1
  • 23
    • 33646544486 scopus 로고    scopus 로고
    • Bestimmung von Aminosäureenantiomeren in Kakao und Kakaoprodukten
    • N Kutz R Pätzold H Brückner 2004 Bestimmung von Aminosäureenantiomeren in Kakao und Kakaoprodukten Lebensmittelchemie 58 106 107
    • (2004) Lebensmittelchemie , vol.58 , pp. 106-107
    • Kutz, N.1    Pätzold, R.2    Brückner, H.3
  • 24
    • 33749101557 scopus 로고
    • New aspects of the Maillard reaction in foods and in the human body
    • F Ledl E Schleicher 1990 New aspects of the Maillard reaction in foods and in the human body Angew Chem Int Ed 29 565 594
    • (1990) Angew Chem Int Ed , vol.29 , pp. 565-594
    • Ledl, F.1    Schleicher, E.2
  • 25
    • 0343301100 scopus 로고
    • Characterization of melanoidin in soy sauce and fish sauce by electrofocusing and high performance gel permeation chromatography
    • YS Lee S Homma K Aida 1987 Characterization of melanoidin in soy sauce and fish sauce by electrofocusing and high performance gel permeation chromatography Nippon Shokuhin Kogyo Gakkaishi 34 313 319
    • (1987) Nippon Shokuhin Kogyo Gakkaishi , vol.34 , pp. 313-319
    • Lee, Y.S.1    Homma, S.2    Aida, K.3
  • 27
    • 0033992504 scopus 로고    scopus 로고
    • A critical appraisal of the kinetic model for the Maillard browning of glucose with glycine
    • DOI 10.1016/S0308-8146(99)00146-6, PII S0308814699001466
    • LP Leong BL Wedzicha 2000 A critical appraisal of the kinetic model for the Maillard browning of glucose and glycine Food Chem 68 21 28 (Pubitemid 29488673)
    • (2000) Food Chemistry , vol.68 , Issue.1 , pp. 21-28
    • Leong, L.P.1    Wedzicha, B.L.2
  • 28
    • 0001329803 scopus 로고
    • Formation de matieres humiques par action de polypeptides sur sucres
    • LC Maillard 1913 Formation de matieres humiques par action de polypeptides sur sucres C R Acad Sci 156 148 149
    • (1913) C R Acad Sci , vol.156 , pp. 148-149
    • Maillard, L.C.1
  • 29
    • 51849181148 scopus 로고
    • Determination of D-amino acids. II. Use of a bifunctional reagent, 1, 5-difluoro-2, 4-dinitrobenzene
    • P Marfey 1984 Determination of D-amino acids. II. Use of a bifunctional reagent, 1, 5-difluoro-2, 4-dinitrobenzene Carlsberg Res Commun 49 591 596
    • (1984) Carlsberg Res Commun , vol.49 , pp. 591-596
    • Marfey, P.1
  • 30
    • 7044231249 scopus 로고    scopus 로고
    • Iron-binding ability of melanoidins from food and model systems
    • DOI 10.1016/j.foodchem.2004.05.030, PII S0308814604004224
    • FJ Morales C Fernandez-Fraguas S Jiménez-Pérez 2005 Iron binding ability of melanoidins from food and model systems Food Chem 90 821 827 (Pubitemid 39424051)
    • (2005) Food Chemistry , vol.90 , Issue.4 , pp. 821-827
    • Morales, F.J.1    Fernandez-Fraguas, C.2    Jimenez-Perez, S.3
  • 31
    • 14644423562 scopus 로고    scopus 로고
    • Peroxyl radical scavenging activity of melanoidins in aqueous systems
    • DOI 10.1007/s00217-004-0896-3
    • FJ Morales S Jiménez-Pérez 2004 Peroxyl radical scavenging activity of melanoidins in aqueous systems Eur Food Res Technol 218 515 520 (Pubitemid 40871407)
    • (2004) European Food Research and Technology , vol.218 , Issue.6 , pp. 515-520
    • Morales, F.J.1    Jimenez-Perez, S.2
  • 32
  • 33
    • 0035961613 scopus 로고    scopus 로고
    • Enantiomeric resolution of amino acids by thin-layer chromatography
    • DOI 10.1016/S1381-1177(00)00209-5, PII S1381117700002095
    • Y Nagata T Lidat M Sakai 2001 Enantiomeric resolution of amino acids by thin-layer chromatography J Mol Catal B Enzym 12 105 108 (Pubitemid 32141135)
    • (2001) Journal of Molecular Catalysis - B Enzymatic , vol.12 , Issue.1-6 , pp. 105-108
    • Nagata, Y.1    Iida, T.2    Sakai, M.3
  • 34
    • 0026731693 scopus 로고
    • The presence of free D-serine, D-alanine and D-proline in human plasma
    • Y Nagata R Masui T Akino 1992 The presence of free D-serine, D-alanine and D-proline in human plasma Experientia 48 986 988
    • (1992) Experientia , vol.48 , pp. 986-988
    • Nagata, Y.1    Masui, R.2    Akino, T.3
  • 35
    • 33646545830 scopus 로고    scopus 로고
    • Mechanistische aspekte und konsequenzen der bildung von D-aminosäuren im laufe der Maillardreaktion
    • R Pätzold H Brückner 2004 Mechanistische aspekte und konsequenzen der bildung von D-aminosäuren im laufe der Maillardreaktion Lebensmittelchemie 58 100
    • (2004) Lebensmittelchemie , vol.58 , pp. 100
    • Pätzold, R.1    Brückner, H.2
  • 36
    • 29744442501 scopus 로고    scopus 로고
    • Mass spectrometric detection and formation of D-amino acids in processed plant saps, syrups, and fruit juice concentrates
    • DOI 10.1021/jf051433u
    • R Pätzold H Brückner 2005 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 (Pubitemid 43027176)
    • (2005) Journal of Agricultural and Food Chemistry , vol.53 , Issue.25 , pp. 9722-9729
    • Patzold, R.1    Bruckner, H.2
  • 37
    • 33745108443 scopus 로고    scopus 로고
    • 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
    • DOI 10.1007/s00217-005-0211-y
    • R Pätzold H Brückner 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 Reaktion Eur Food Res Technol 223 347 354 (Pubitemid 43883112)
    • (2006) European Food Research and Technology , vol.223 , Issue.3 , pp. 347-354
    • Patzold, R.1    Bruckner, H.2
  • 38
    • 33746145164 scopus 로고    scopus 로고
    • Gas chromatographic determination and mechanism of formation of D-amino acids occurring in fermented and roasted cocoa beans, cocoa powder, chocolate and cocoa shell
    • DOI 10.1007/s00726-006-0330-1
    • R Pätzold H Brückner 2006 Gas chromatographic determination and mechanism of formation of D-amino acids occurring in fermented and roasted cocoa beans, cocoa powder, chocolate and other cocoa products Amino Acids 31 63 72 (Pubitemid 44086399)
    • (2006) Amino Acids , vol.31 , Issue.1 , pp. 63-72
    • Patzold, R.1    Bruckner, H.2
  • 39
    • 0037619050 scopus 로고    scopus 로고
    • Chiral gas chromatographic analysis of amino acids in fortified wines
    • R Pätzold A Nieto-Rodriguez H Brückner 2003 Chiral gas chromatographic analysis of amino acids in fortified wines Chromatographia 57 Suppl S207 S212
    • (2003) Chromatographia , vol.57 , Issue.SUPPL.
    • Pätzold, R.1    Nieto-Rodriguez, A.2    Brückner, H.3
  • 40
    • 11744286228 scopus 로고
    • Considerations of chiral recognition relevant to the liquid chromatographic separation of enantiomers
    • WH Pirkle TC Pochapsky 1989 Considerations of chiral recognition relevant to the liquid chromatographic separation of enantiomers Chem Rev 89 347 362
    • (1989) Chem Rev , vol.89 , pp. 347-362
    • Pirkle, W.H.1    Pochapsky, T.C.2
  • 41
    • 1642294131 scopus 로고    scopus 로고
    • Decoloration de solutions sucrees par ultra-filtration sur une membrane a base de poly(organocyclophosphazene)
    • PII S0014305796002327
    • M Rafik A Mas A Elharfi F Schue 1997 Decoloration de solutions sucrees par ultrafiltration sur une membrane a base de poly(organocyclophosphazene) Eur Polymer J 33 679 690 (Pubitemid 127388050)
    • (1997) European Polymer Journal , vol.33 , Issue.5 , pp. 679-690
    • Rafik, M.1    Mas, A.2    Elharfi, A.3    Schue, F.4
  • 42
    • 0031285767 scopus 로고    scopus 로고
    • Chemical structure of colored Maillard reaction products
    • GP Rizzi 1997 Chemical structure of coloured Maillard reactions products Food Rev Int 13 1 28 (Pubitemid 127339705)
    • (1997) Food Reviews International , vol.13 , Issue.1 , pp. 1-28
    • Rizzi, G.P.1
  • 43
    • 0015072056 scopus 로고
    • Fluorescence reaction for amino acids
    • M Roth 1971 Fluorescence reaction for amino acids Anal Chem 43 880 882
    • (1971) Anal Chem , vol.43 , pp. 880-882
    • Roth, M.1
  • 44
    • 67349226414 scopus 로고    scopus 로고
    • A screening procedure to assess the antimicrobial activity of melanoidins
    • Melanoidins in food and health, Hamburg, Germany, July 2004
    • Rufián-Henares JA, Morales FJ (2005) A screening procedure to assess the antimicrobial activity of melanoidins. Oral presentation at COST Action 919, Melanoidins in food and health, Hamburg, Germany, July 2004
    • (2005) Oral Presentation at COST Action 919
    • Rufián-Henares, J.A.1    Morales, F.J.2
  • 45
    • 67349198127 scopus 로고    scopus 로고
    • Graduation thesis, Technical University of Lisbon, Portugal and Wageningen University, The Netherlands
    • Sara IFSM (1997) Kinetic modelling of glucose and glycine. Graduation thesis, Technical University of Lisbon, Portugal and Wageningen University, The Netherlands
    • (1997) Kinetic Modelling of Glucose and Glycine
    • Ifsm, S.1
  • 46
    • 0041664980 scopus 로고    scopus 로고
    • Melanoidins extinction coefficient in the glucose/glycine Maillard reaction
    • DOI 10.1016/S0308-8146(03)00219-X
    • IFSM Sara MAJS Van Boekel 2003 Melanoidins extinction coefficient in the glucose/glycine Maillard reaction Food Chem 83 135 142 (Pubitemid 36945464)
    • (2003) Food Chemistry , vol.83 , Issue.1 , pp. 135-142
    • Martins, S.I.F.S.1    Van Boekel, M.A.J.S.2
  • 47
    • 33748459220 scopus 로고
    • The Lobry de Bruyn-Alberda van Ekenstein transformation
    • JCJ Speck 1958 The Lobry de Bruyn-Alberda van Ekenstein transformation Adv Carbohydr Chem 13 63 103
    • (1958) Adv Carbohydr Chem , vol.13 , pp. 63-103
    • Speck, J.C.J.1
  • 48
    • 0023895617 scopus 로고
    • Application of Marfey's reagent in racemization studies of amino acids and peptides
    • DOI 10.1016/S0021-9673(01)94014-2
    • G Szókán G Mezo F Hudecz 1988 Application of Marfey's Reagent in racemization studies of amino acids and peptides J Chromatogr 444 115 122 (Pubitemid 18166753)
    • (1988) Journal of Chromatography , vol.444 , pp. 115-122
    • Szokan, G.1    Mezo, G.2    Hudecz, F.3
  • 50
    • 0001666638 scopus 로고    scopus 로고
    • Kinetic modelling of sugar reactions in heated milk-like systems
    • MAJS Van Boekel 1996 Kinetic modelling of sugar reactions in heated milk-like systems Neth Milk Dairy J 50 245 266
    • (1996) Neth Milk Dairy J , vol.50 , pp. 245-266
    • Van Boekel Majs1
  • 51
    • 0026629213 scopus 로고
    • Spectrophotometric assay using o-phthaldiadehyde for determination of reactive lysine in dairy products
    • MS Vigo LS Malec RG Gomez RA Llosa 1992 Spectrophotometric assay using o-phthaldiadehyde for determination of reactive lysine in dairy products Food Chem 44 363 365
    • (1992) Food Chem , vol.44 , pp. 363-365
    • Vigo, M.S.1    Malec, L.S.2    Gomez, R.G.3    Llosa, R.A.4
  • 52
    • 0026525882 scopus 로고
    • Melanoidins from glucose and glycine: Composition, characteristics and reactivity towards sulphite ion
    • BL Wedzicha MT Kaputo 1992 Melanoidins from glucose and glycine: composition, characteristics and reactivity towards sulphite ion Food Chem 43 359 367
    • (1992) Food Chem , vol.43 , pp. 359-367
    • Wedzicha, B.L.1    Kaputo, M.T.2
  • 53
    • 0001039109 scopus 로고    scopus 로고
    • Reaction Conditions Influence the Elementary Composition and Metal Chelating Affinity of Nondialyzable Model Maillard Reaction Products
    • AN Wijewickreme DD Kitts TD Durance 1997 Reaction conditions influence the elementary composition and metal chelating affinity of nondialyzable model Maillard reaction products J Agric Food Chem 45 4577 4583 (Pubitemid 127485807)
    • (1997) Journal of Agricultural and Food Chemistry , vol.45 , Issue.12 , pp. 4577-4583
    • Wijewickreme, A.N.1    Kitts, D.D.2    Durance, T.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.