메뉴 건너뛰기




Volumn 57, Issue 11, 2009, Pages 4765-4770

Reactivity of 1-deoxy-D-erythro-hexo-2,3-diulose; A key intermediate in the maillard chemistry of hexoses

Author keywords

Dicarbonyl compounds; 1 deoxyglucosone; 1 deoxyhexo 2,3 diulose; Acetic acid; Carbohydrate degradation; Dicarbonyl cleavage; Maillard reaction

Indexed keywords

1 DEOXY ERYTHRO HEXO 2,3 DIULOSE; 1-DEOXY-ERYTHRO-HEXO-2,3-DIULOSE; HEXOSE; KETOSE;

EID: 67149138148     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf900459x     Document Type: Article
Times cited : (35)

References (26)
  • 1
    • 33947448299 scopus 로고
    • Dehydrated foods: Chemistry of browning reactions in model systems
    • Hodge, J. E. Dehydrated foods: chemistry of browning reactions in model systems. J. Agric. Food Chem. 1953, 1, 928-943.
    • (1953) J. Agric. Food Chem , vol.1 , pp. 928-943
    • Hodge, J.E.1
  • 2
    • 0000407561 scopus 로고
    • Die Maillard-Reaktion in Lebensmitteln und im menschlichen Körper - neue Ergebnisse zu Chernie, Bochemie und Medizin
    • Ledl, F.; Schleicher, E. Die Maillard-Reaktion in Lebensmitteln und im menschlichen Körper - neue Ergebnisse zu Chernie, Bochemie und Medizin. Angew. Chem. 1990, 102, 597-626.
    • (1990) Angew. Chem , vol.102 , pp. 597-626
    • Ledl, F.1    Schleicher, E.2
  • 3
  • 4
    • 0001536872 scopus 로고
    • 3-Deoxyglycosuloses (3-deoxyglycosones) and the degradation of carbohydrates
    • Anet, E. F. L. J. 3-Deoxyglycosuloses (3-deoxyglycosones) and the degradation of carbohydrates. Adv. Carhohydr. Chem 1964, 19, 181-218.
    • (1964) Adv. Carhohydr. Chem , vol.19 , pp. 181-218
    • Anet, E.F.L.J.1
  • 5
    • 0035188656 scopus 로고    scopus 로고
    • Detection of alpha-dicarbonyl compounds in Maillard reaction systems and in vivo
    • Glomb, M. A.; Tschimich, R. Detection of alpha-dicarbonyl compounds in Maillard reaction systems and in vivo. J. Agric. Food Chem. 2001, 49, 5543-5550.
    • (2001) J. Agric. Food Chem , vol.49 , pp. 5543-5550
    • Glomb, M.A.1    Tschimich, R.2
  • 6
    • 0344085934 scopus 로고
    • 2,3-Dihydro-3,5-dihydroxy-6- methyl-4H-pyran-4-one, a novel nonenzymatic browning product
    • Mills, F. D.; Weisleder, D.; Hodge, J. E. 2,3-Dihydro-3,5-dihydroxy-6- methyl-4H-pyran-4-one, a novel nonenzymatic browning product. Tetrahedron Lett. 1970, 11, 1243-1246.
    • (1970) Tetrahedron Lett , vol.11 , pp. 1243-1246
    • Mills, F.D.1    Weisleder, D.2    Hodge, J.E.3
  • 7
    • 0344085932 scopus 로고
    • Proof of 2,3-dihydro-3,5-dihy-droxy-6- methyl-4H-pyran-4-on in foods. Studies on Maillard reaction XI
    • Ledl, F.; Schnell, W.; Severin, T. Proof of 2,3-dihydro-3,5-dihy-droxy-6- methyl-4H-pyran-4-on in foods. Studies on Maillard reaction XI. Z. Lebensm. Unters.-Forsch 1976, 160, 367-370.
    • (1976) Z. Lebensm. Unters.-Forsch , vol.160 , pp. 367-370
    • Ledl, F.1    Schnell, W.2    Severin, T.3
  • 8
    • 0001696723 scopus 로고    scopus 로고
    • On the role of 2,3-dihydro-3,5-dihydroxy-6-methyl- 4(H)-pyran-4-one in the Maillard reaction
    • Kim, M. O.; Baltes, W. On the role of 2,3-dihydro-3,5-dihydroxy-6-methyl- 4(H)-pyran-4-one in the Maillard reaction. J. Agric. Food Chem. 1996, 44, 282-289.
    • (1996) J. Agric. Food Chem , vol.44 , pp. 282-289
    • Kim, M.O.1    Baltes, W.2
  • 9
    • 0000334043 scopus 로고    scopus 로고
    • A chemical switch in the formation of colored Maillard reaction products from hexoses and primary and secondary amino acids
    • Hofmann, T. Acetylformoin: A chemical switch in the formation of colored Maillard reaction products from hexoses and primary and secondary amino acids. J. Agric, Food Chem. 1998, 46, 3918-3928.
    • (1998) J. Agric, Food Chem , vol.46 , pp. 3918-3928
    • Hofmann, T.A.1
  • 10
    • 0000492295 scopus 로고
    • Maillard reaction. II. Reaction of pentoses in the presence of amine acetates
    • Severin, Th.; Seilmeier, W. Maillard reaction. II. Reaction of pentoses in the presence of amine acetates. Z. Lebensm. Unters.-Forsch. 1967, 134, 230-232.
    • (1967) Z. Lebensm. Unters.-Forsch , vol.134 , pp. 230-232
    • Severin, T.1    Seilmeier, W.2
  • 11
    • 0000720285 scopus 로고
    • Isolation of 4-hydroxy-2-(hydroxy- methyl)-5-metliyl-3(2H)-furanone from sugar amino-acid reaction mixtures
    • Hiebl, J.; Ledl, F.; Severin, T. Isolation of 4-hydroxy-2-(hydroxy- methyl)-5-metliyl-3(2H)-furanone from sugar amino-acid reaction mixtures. J. Agric. Food Chem. 1987, 35, 990-993.
    • (1987) J. Agric. Food Chem , vol.35 , pp. 990-993
    • Hiebl, J.1    Ledl, F.2    Severin, T.3
  • 12
    • 33748898073 scopus 로고    scopus 로고
    • Sugar fragmentation in the Maillard reaction cascade: Isotope labeling studies on the formation of acetic acid by a hydrolytic beta-dicarbonyl cleavage mechanism
    • Davidek, T.; Devaud, S.; Robert, F.; Blank, I. Sugar fragmentation in the Maillard reaction cascade: Isotope labeling studies on the formation of acetic acid by a hydrolytic beta-dicarbonyl cleavage mechanism. J. Agric. Food Chem. 2006, 54, 6667-6676.
    • (2006) J. Agric. Food Chem , vol.54 , pp. 6667-6676
    • Davidek, T.1    Devaud, S.2    Robert, F.3    Blank, I.4
  • 13
    • 33748887417 scopus 로고    scopus 로고
    • Sugar fragmentation in the Maillard reaction cascade: Formation of short-chain carboxylic acids by a new oxidative alpha-dicarbonyl cleavage pathway
    • Davidek, T.; Robert, F.; Devaud, S.; Vera, F. A.; Blank, I. Sugar fragmentation in the Maillard reaction cascade: Formation of short-chain carboxylic acids by a new oxidative alpha-dicarbonyl cleavage pathway. J. Agric. Food Chem. 2006, 54, 6677-6684.
    • (2006) J. Agric. Food Chem , vol.54 , pp. 6677-6684
    • Davidek, T.1    Robert, F.2    Devaud, S.3    Vera, F.A.4    Blank, I.5
  • 14
    • 23744506296 scopus 로고    scopus 로고
    • Elucidation of Chemical Pathways in the Maillard Reaction by O-17-NMR Spectroscopy
    • Baynes, J. W, Monnier, V. M, Ames, J. M, Thorpe, S. R, Eds, Annals of the New York Academy of Sciences; Wiley: New York
    • Robert, F.; Vera, F. A.; Kervella, F.; Davidek, T.; Blank, I. Elucidation of Chemical Pathways in the Maillard Reaction by O-17-NMR Spectroscopy. In The Maillard Reaction: Chemistry at the Interface of Nutrition, Aging, and Disease; Baynes, J. W., Monnier, V. M., Ames, J. M., Thorpe, S. R., Eds.; Annals of the New York Academy of Sciences; Wiley: New York, 2005; Vol. 1043, pp 63-72.
    • (2005) The Maillard Reaction: Chemistry at the Interface of Nutrition, Aging, and Disease , vol.1043 , pp. 63-72
    • Robert, F.1    Vera, F.A.2    Kervella, F.3    Davidek, T.4    Blank, I.5
  • 15
    • 0034680714 scopus 로고    scopus 로고
    • Synthesis of l-deoxy-D-erythro-hexo-2,3- diulose, a major hexose Maillard intermediate
    • Glomb, M. A.; Pfahler, C. Synthesis of l-deoxy-D-erythro-hexo-2,3- diulose, a major hexose Maillard intermediate. Carhohydr. Res. 2000, 329, 515-523.
    • (2000) Carhohydr. Res , vol.329 , pp. 515-523
    • Glomb, M.A.1    Pfahler, C.2
  • 17
    • 0026067029 scopus 로고
    • Amino-acid derivatization and analysis in 5 minutes
    • Husek, P. Amino-acid derivatization and analysis in 5 minutes. FEBS Lett. 1991, 280, 354-356.
    • (1991) FEBS Lett , vol.280 , pp. 354-356
    • Husek, P.1
  • 18
    • 33947291896 scopus 로고
    • Gas Chromatographic method for determination of sugars in foods
    • Mason, B. S.; Slover, H. T. Gas Chromatographic method for determination of sugars in foods. J. Agric. Food Chem. 1971, 19, 551-554.
    • (1971) J. Agric. Food Chem , vol.19 , pp. 551-554
    • Mason, B.S.1    Slover, H.T.2
  • 19
    • 0034775565 scopus 로고    scopus 로고
    • Reactions of mono-saccharides during heating of sugar-casein systems: Building of a reaction network model
    • Brands, C.M. J.; van Boekel, M.A. J. S. Reactions of mono-saccharides during heating of sugar-casein systems: Building of a reaction network model. J. Agric. Food Chem. 2001, 49, 4667-4675.
    • (2001) J. Agric. Food Chem , vol.49 , pp. 4667-4675
    • Brands, C.M.J.1    van Boekel, M.A.J.S.2
  • 20
    • 33947308422 scopus 로고    scopus 로고
    • Electrospray ionization mass spectrometric investigations of alpha-dicarbonyl compounds: Probing intermediates formed in the course of the nonenzymatic browning reaction of L-ascorbic acid
    • Schulz, A.; Trage, C.; Schwarz, H.; Kroh, L. W. Electrospray ionization mass spectrometric investigations of alpha-dicarbonyl compounds: Probing intermediates formed in the course of the nonenzymatic browning reaction of L-ascorbic acid. Int. J. Mass. Spectrom. 2007, 262, 169-173.
    • (2007) Int. J. Mass. Spectrom , vol.262 , pp. 169-173
    • Schulz, A.1    Trage, C.2    Schwarz, H.3    Kroh, L.W.4
  • 21
    • 0000945315 scopus 로고
    • Detection of 5-hydroxymethyl-2- methyl-3(2H)-furanone and of alpha-dicarbonyl compounds in reaction mixtures of hexoses and pentoses with different amines
    • Nedvidek, W.; Ledl, F.; Fischer, P. Detection of 5-hydroxymethyl-2- methyl-3(2H)-furanone and of alpha-dicarbonyl compounds in reaction mixtures of hexoses and pentoses with different amines. Z. Lebensm. Unters.-Forsch. 1992, 194, 222-228
    • (1992) Z. Lebensm. Unters.-Forsch , vol.194 , pp. 222-228
    • Nedvidek, W.1    Ledl, F.2    Fischer, P.3
  • 22
    • 43049180864 scopus 로고
    • Studies on the chemical decomposition of simple sugars 0.10. Acetol formation from C-14-labeled hexoses
    • Goto, R.; Hayami, J.; Kudo, K.; Otani, S. Studies on the chemical decomposition of simple sugars 0.10. Acetol formation from C-14-labeled hexoses. Bull. Chem. Soc. Jpn. 1961, 34, 753-757.
    • (1961) Bull. Chem. Soc. Jpn , vol.34 , pp. 753-757
    • Goto, R.1    Hayami, J.2    Kudo, K.3    Otani, S.4
  • 23
    • 33748820836 scopus 로고
    • Studies on the chemical decomposition of simple sugars. XII. Mechanism of the acetol formation
    • Hayami, J. Studies on the chemical decomposition of simple sugars. XII. Mechanism of the acetol formation. Bull. Chem. Soc. Jpn. 1961, 34, 927-932.
    • (1961) Bull. Chem. Soc. Jpn , vol.34 , pp. 927-932
    • Hayami, J.1
  • 24
    • 0032142790 scopus 로고    scopus 로고
    • Reactive intermediates and carbohydrate fragmentation in Maillard chemistry
    • Weenen, H. Reactive intermediates and carbohydrate fragmentation in Maillard chemistry. Food Chem. 1998, 62, 393-401.
    • (1998) Food Chem , vol.62 , pp. 393-401
    • Weenen, H.1
  • 25
    • 0033948390 scopus 로고    scopus 로고
    • Origin of carbohydrate degradation products in L-alanine/D-[C-13]glucose model systems
    • Yaylayan, V. A.; Keyhani, A. Origin of carbohydrate degradation products in L-alanine/D-[C-13]glucose model systems. J. Agric. Food Chem. 2000, 48, 2415-2419.
    • (2000) J. Agric. Food Chem , vol.48 , pp. 2415-2419
    • Yaylayan, V.A.1    Keyhani, A.2
  • 26
    • 0035111282 scopus 로고    scopus 로고
    • Carbohydrate and amino acid degradation pathways in L-methionine/D-[C-13] glucose model systems
    • Yaylayan, V. A.; Keyhani, A. Carbohydrate and amino acid degradation pathways in L-methionine/D-[C-13] glucose model systems. J. Agric. Food Chem. 2001, 49, 800-803.
    • (2001) J. Agric. Food Chem , vol.49 , pp. 800-803
    • Yaylayan, V.A.1    Keyhani, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.