FORMATION OF PYRROLES, 2-PYRROLIDONES, AND PYRIDONES BY HEATING OF 4-AMINOBUTYRIC ACID AND REDUCING SUGARS

被引:22
作者
TRESSL, R [1 ]
KERSTEN, E [1 ]
REWICKI, D [1 ]
机构
[1] FREE UNIV BERLIN,D-14195 BERLIN 33,GERMANY
关键词
D O I
10.1021/jf00035a057
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
The Maillard reaction of 4-aminobutyric acid with reducing sugars (D-arabinose, D-glucose, L-rhamnose, D-fructose, maltose) was investigated in slightly acidic aqueous media. Eight pyrroles, 142-pyrrolidones, and 2 4-pyridones were characterized and quantified by capillary GC/MS. For structure elucidation the compounds were separated by preparative GC or synthesized and investigated by MS, IR, and H-1 NMR spectroscopy. Due to a blocked Strecker degradation, the 4-aminobutyric acid specific Maillard products are comparable to those of peptide-bound L-lysine. Thus, the title compounds generated in D-glucose and maltose/4-aminobutyric acid model experiments are structurally related to epsilon-pyrrolonor-leucine and maltosine, respectively.
引用
收藏
页码:2125 / 2130
页数:6
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