Synthesis of 1-deoxy-D-erythro-hexo-2,3-diulose, a major hexose Maillard intermediate

被引:34
作者
Glomb, MA [1 ]
Pfahler, C [1 ]
机构
[1] Tech Univ Berlin, Inst Food Chem, D-13355 Berlin, Germany
关键词
1-deoxy-D-erythro-hexo-2,3-diulose; Maillard reaction; protein modification; Browning; C-2(5) chair;
D O I
10.1016/S0008-6215(00)00219-6
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
1-Deoxy-D-erythro-hexo-2,3-diulose (1-DG) was prepared by the reaction of ethoxyvinyllithium with an erythrono-lactone derivative. Characterization by H-1 and C-13 NMR spectroscopy and NOE difference experiments revealed the C-2(5)-chair beta -pyranose as the major isomer in solution. Experiments assessing browning and polymerization reactivity proved I-DG to be a much more potent protein modifier than 3-deoxy-D-erythro-hexos-2-ulose. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:515 / 523
页数:9
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