Pyridinium-carbaldehyde: active Maillard reaction product from the reaction of hexoses with lysine residues
作者:Oliver Reihl、Klaus M. Biemel、Markus O. Lederer、Wolfgang Schwack
DOI:10.1016/j.carres.2003.12.009
日期:2004.2
Besides the formation of the aminotriazine N6-[4-(3-amino-1,2,4-triazin-5-yl)-2,3-dihydroxybutyl]-L-lysine, the reaction of [1-13C]D-glucose with lysine and aminoguanidine leads to the generation of 6-[2-([[amino(imino)methyl]hydrazono]methyl)pyridinium-1-yl]-L-norleucine (14-13C1). The dideoxyosone N6-(2,3-dihydroxy-5,6-dioxohexyl)-L-lysine was shown to be a precursor in the formation of 14-13C1,
除了形成氨基三嗪N6- [4-(3-氨基-1,2,4-三嗪-5-基)-2,3-二羟基丁基] -L-赖氨酸外,[1-13C] D-的反应葡萄糖与赖氨酸和氨基胍一起导致生成6- [2-([[((氨基(亚氨基)甲基]肼基]甲基)吡啶-1-基] -L-正亮氨酸(14-13C1)。已显示双脱氧松酮N6-(2,3-二羟基-5,6-二氧己基)-L-赖氨酸是14-13C1形成的前体,其通过反应性羰基中间体6-(2-甲酰基吡啶鎓-1)进行-yl)-L-正亮氨酸(13-13C1)。为了研究13-13C1的反应性,从2-吡啶甲醇开始,分两步制备了模型化合物1-丁基-2-甲酰基吡啶鎓(18)。吡啶鎓甲醛18与L-赖氨酸的反应产生了Strecker类似的降解产物2-(氨基甲基)-1-丁基吡啶鎓和另一种化合物,显示为1-丁基-2-[((2-氧代哌啶-3-亚甲基)甲基]吡啶鎓。18与CH酸性4-羟基-5-甲基呋喃-3(