Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, PL-60-780 Poznań.
Chem Biodivers. 2010 Apr;7(4):959-74. doi: 10.1002/cbdv.200800320.
The reactions of adenosine with malonaldehyde and glyoxal, and with malonaldehyde and methylglyoxal resulted in the formation of one malonaldehyde-glyoxal and one malonaldehyde-methylglyoxal conjugate adduct, respectively. These adducts were isolated and purified by reversed-phase liquid chromatography, and structurally characterized by UV, (1)H- and (13)C-NMR spectroscopy, and mass spectrometry. The malonaldehyde-glyoxal adduct was identified as 8-(diformylmethyl)-3-(beta-D-ribofuranosyl)imidazo[2,1-i]purine (M(1)Gx-A), while the malonaldehyde-methylglyoxal one as 8-(diformylmethyl)-7-methyl-3-(beta-D-ribofuranosyl)imidazo[2,1-i]purine (M(1)MGx-A). Both adducts were also observed in calf thymus DNA when incubated in the respective aldehydes under physiological pH and temperature. Moreover, in the reaction of methylglyoxal and malonaldehyde with adenosine, an additional adduct was formed. This adduct was found to consist of one unit derived from methylglyoxal and one unit from formaldehyde. The adduct was identified as N(6)-(2,3-dihydroxy-2-methylpropanoyl)-9-(beta-D-ribofuranosyl)purine (MGxFA-A). Formaldehyde was found to originate from the commercial methylglyoxal in which it was present as an impurity.
腺嘌呤分别与丙二醛和乙二醛、以及与丙二醛和甲基乙二醛反应，分别生成一个丙二醛-乙二醛和一个丙二醛-甲基乙二醛缀合加合物。这些加合物通过反相液相色谱法分离和纯化，并通过紫外、（1）H-和（13）C-NMR 光谱以及质谱法进行结构表征。丙二醛-乙二醛加合物被鉴定为 8-(二醛基甲基)-3-(β-D-核糖呋喃基)咪唑并[2,1-i]嘌呤（M(1)Gx-A），而丙二醛-甲基乙二醛加合物被鉴定为 8-(二醛基甲基)-7-甲基-3-(β-D-核糖呋喃基)咪唑并[2,1-i]嘌呤（M(1)MGx-A）。当在生理 pH 值和温度下在各自的醛中孵育时，小牛胸腺 DNA 中也观察到这两种加合物。此外，在甲基乙二醛和丙二醛与腺嘌呤的反应中，还形成了另一个加合物。该加合物被发现由一个来自甲基乙二醛的单元和一个来自甲醛的单元组成。该加合物被鉴定为 N(6)-(2,3-二羟基-2-甲基丙酰基)-9-(β-D-核糖呋喃基)嘌呤（MGxFA-A）。甲醛是从商用甲基乙二醛中产生的，其中它作为杂质存在。
