Carbohydrate carbonyl mobility -: the key process in the formation of α-dicarbonyl intermediates

被引：24

作者：

Reihl, O ^{[1
]}

Rothenbacher, TM ^{[1
]}

Lederer, MO ^{[1
]}

Schwack, W ^{[1
]}

机构：

[1] Univ Hohenheim, Inst Lebensmittelchem 170, D-70593 Stuttgart, Germany

来源：

CARBOHYDRATE RESEARCH | 2004年 / 339卷 / 09期

关键词：

Maillard reaction; quinoxaline; dideoxyosone; o-phenylenediamine (OPD); advanced glycation end product (AGE);

D O I：

10.1016/j.carres.2004.03.024

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Covalently cross-linked proteins are among the major modifications caused by the advanced Maillard reaction. In the present study, the formation pathway of the dideoxyosone N-6-(2,3-dihydroxy-5,6-dioxohexyl)-L-lysine is shown. To elucidate the formation of this glucose-derived dideoxyosone D-lactose (O-beta-D-galp-(1 --> 4)-D-glcp) and D-glucose-6-phosphate were incubated with lysine in the presence of the trapping reagent o-phenylenediamine (OPD). Synthesis and unequivocal structural characterization were reported for the quinoxalines of the dideoxyosones N6-(5,6-dihydroxy-2,3-dioxohexyl)-L-lysine and N-6-(2,3-dihydroxy-4,5-dioxohexyl)-L-lysine, respectively. Additionally, dicarbonyl compounds derived from D-erythrose, D-glycero-D-mannoheptose, and D-gluco-L-talooctose were synthesized and structurally characterized. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：1609 / 1618

页数：10

共 26 条

[1] Role of oxidative stress in diabetic complications - A new perspective on an old paradigm [J].

Baynes, JW ;

Thorpe, SR .

DIABETES, 1999, 48 (01) :1-9

[2] Site-specific quantitative evaluation of the protein glycation product N6-(2,3-dihydroxy-5,6-dioxohexyl)-L-lysinate by LC-(ESI)MS peptide mapping:: Evidence for its key role in AGE formation [J].

Biemel, KM ;

Lederer, MO .

BIOCONJUGATE CHEMISTRY, 2003, 14 (03) :619-628

[3]

Biemel KM, 2002, ANGEW CHEM INT EDIT, V41, P801, DOI 10.1002/1521-3773(20020301)41:5<801::AID-ANIE801>3.0.CO

[4]

2-I

[5] Formation pathways for lysine-arginine cross-links derived from hexoses and pentoses by Maillard processes - Unraveling the structure of a pentosidine precursor [J].

Biemel, KM ;

Reihl, O ;

Conrad, J ;

Lederer, MO .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (26) :23405-23412

[6]

Colaco C. A. L. S., 1997, The Glycation Hypothesis of Atherosclerosis

[7]

FEATHER MS, 1998, ROYAL SOC CHEM, V223, P37

[8] Food browning and its prevention: An overview [J].

Friedman, M .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1996, 44 (03) :631-653

[9] Detection of α-dicarbonyl compounds in Maillard reaction systems and in vivo [J].

Glomb, MA ;

Tschirnich, R .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (11) :5543-5550

[10] Synthesis of 1-deoxy-D-erythro-hexo-2,3-diulose, a major hexose Maillard intermediate [J].

Glomb, MA ;

Pfahler, C .

CARBOHYDRATE RESEARCH, 2000, 329 (03) :515-523

← 1 2 3 →