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

[21]

SHIN DB, 1988, AGR BIOL CHEM TOKYO, V52, P1451

[22] Advanced glycation end products co-localized with astrocytes and microglial cells in Alzheimer's disease brain [J].

Takeda, A ;

Yasuda, T ;

Miyata, T ;

Goto, Y ;

Wakai, M ;

Watanabe, M ;

Yasuda, Y ;

Horie, K ;

Inagaki, T ;

Doyu, M ;

Maeda, K ;

Sobue, G .

ACTA NEUROPATHOLOGICA, 1998, 95 (06) :555-558

[23] Protein glycation, diabetes, and aging [J].

Ulrich, P ;

Cerami, A .

RECENT PROGRESS IN HORMONE RESEARCH, VOL 56, 2001, 56 :1-21

[24] An agent cleaving glucose-derived protein crosslinks in vitro and in vivo [J].

Vasan, S ;

Zhang, X ;

Zhang, XN ;

Kapurniotu, A ;

Bernhagen, J ;

Teichberg, S ;

Basgen, J ;

Wagle, D ;

Shih, D ;

Terlecky, I ;

Bucala, R ;

Cerami, A ;

Egan, J ;

Ulrich, P .

NATURE, 1996, 382 (6588) :275-278

[25] ADVANCED GLYCATION END-PRODUCTS INDUCE GLOMERULAR SCLEROSIS AND ALBUMINURIA IN NORMAL RATS [J].

VLASSARA, H ;

STRIKER, LJ ;

TEICHBERG, S ;

FUH, H ;

LI, YM ;

STEFFES, M .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1994, 91 (24) :11704-11708

[26] RAGE and amyloid-beta peptide neurotoxicity in Alzheimer's disease [J].

Yan, SD ;

Chen, X ;

Fu, J ;

Chen, M ;

Zhu, HJ ;

Roher, A ;

Slattery, T ;

Zhao, L ;

Nagashima, M ;

Morser, J ;

Migheli, A ;

Nawroth, P ;

Stern, D ;

Schmidt, AM .

NATURE, 1996, 382 (6593) :685-691

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