Isolation and characterization of glyoxal-arginine modifications
Isolation and characterization of glyoxal-arginine modifications
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DOI：
10.1021/jf001082d
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发表时间：
2001-03-01
影响因子：
6.1
通讯作者：
Lang, G
中科院分区：
文献类型：
--
作者：
Glomb, MA;Lang, G
5-(4，5-Dihydroxy-2-imino-1-imidazolidinyl)norvaline(1)是精氨酸与乙二醛早期反应的唯一产物，该产物被缓慢降解为N-5-[(羧甲基)氨基](亚氨基)甲基]鸟氨酸(3，N-7-羧甲基精氨酸)。在反应条件下，在pH 4-8和20-50℃的范围内没有检测到其他结构。两种产物的生成速率均随pH和温度的升高而增加。在平衡状态下，1的乙烯二醇基团有86%是反式构型的。1的形成是可逆的，这可以通过分离的异构体的顺反异构化和精氨酸在二羰基捕捉剂、邻苯二胺和氨基胍存在下的再生来证明。只有在强酸性条件下，1和3才能转化为5-(2-亚氨基-5-氧代-1-咪唑烷基)去甲戊氨酸(2)。
5-(4,5-Dihydroxy-2-imino-1-imidazolidinyl)norvaline (1) was identified as the only product of the early reaction of arginine with glyoxal, which was slowly degraded to N-5-[[(carboxymethyl)amino] (imino)methyl] ornithine (3, N-7-carboxymethylarginine). No other structures could be detected within a range of pH 4-8 and 20-50 degreesC in reaction conditions. The rates of formation for both products increased with pH and temperature. In equilibrium, the vincinal diol groups of 1 were 86% trans configured. The formation of 1 was reversible, as could be shown by cis-trans isomerization of the separated isomers and by regeneration of arginine in the presence of the ol-dicarbonyl trapping reagents, o-phenylenediamine and aminoguanidine. Both 1 and 3 were converted to 5-(2-imino-5-oxo-1-imidazolidinyl)norvaline (2) only under strong acidic conditions.