Possible involvement of dihydrofructosazine in the DNA breaking activity of D-glucosamine.
Possible involvement of dihydrofructosazine in the DNA breaking activity of D-glucosamine.
复制标题
二氢果糖嗪可能参与 D-葡萄糖胺的 DNA 断裂活性。
DOI：
10.1248/bpb.18.653
复制
发表时间：
1995
影响因子：
2
通讯作者：
K. Watanabe
中科院分区：
文献类型：
--
作者：
N. Kashige;T. Yamaguchi;N. Mishiro;H. Hanazono;F. Miake;K. Watanabe
D-氨基葡萄糖盐酸盐经阴离子交换树脂脱氯化氢后，对质粒pBR 322的DNA断裂活性明显提高，尤其是在Cu ~（2+）存在下。经阴离子交换剂处理的D-氨基葡萄糖盐酸盐样品，即，无HCl的D-葡糖胺样品在水中的UV吸收光谱上在274 nm处显示出最大吸收，如在果糖嗪[2，5-双（D-阿拉伯糖基-四羟基丁基）吡嗪]（D-葡糖胺的二聚体之一）的情况下所见。在正离子快原子轰击（FAB）质谱上，样品显示m/z 323处的离子峰作为基峰，对应于二氢果糖嗪[2，5-双（D-阿拉伯糖基-四羟基丁基）二氢吡嗪]（果糖嗪的前体）以及D-葡糖胺本身（m/z 180）和果糖嗪（m/z 321）的离子峰。无盐酸的D-氨基葡萄糖样品的DNA链断裂活性与m/z 323离子峰强度成正比，而果糖嗪的DNA断裂活性远弱于无盐酸的D-氨基葡萄糖样品。具有与二氢果糖嗪相同的二氢吡嗪骨架的2，5-二氢-3，6-二甲基吡嗪和2，3-二氢-5，6-二甲基吡嗪显示出与无HCl的D-葡糖胺样品相同程度的DNA链断裂活性。这些结果表明，在脱氯化氢过程中产生的二氢果糖嗪与无HCl的D-氨基葡萄糖样品的DNA断裂活性密切相关。
Dehydrochlorination of D-glucosamine (2-amino-2-deoxy-D-glucose) hydrochloride with an anion exchange resin made its DNA breaking activity in plasmid pBR322 much higher, especially in the presence of Cu2+. The sample of anion exchanger-treated D-glucosamine hydrochloride, i.e., HCL-free D-glucosamine sample, showed an absorption maximum at 274 nm on the UV absorption spectrum in water as seen in the case of fructosazine [2,5-bis(D-arabino-tetrahydroxybutyl)pyrazine] one of the dimers of D-glucosamine. On a positive-ion fast atom bombardment (FAB) mass spectrum, the sample showed an ion peak at m/z 323 as a base peak, corresponding to dihydrofructosazine [2,5-bis(D-arabino-tetrahydroxybutyl) dihydropyrazine], which was a precursor of fructosazine, as well as those of D-glucosamine itself (m/z 180) and fructosazine (m/z 321). The DNA strand breaking activity of HCL-free D-glucosamine sample was directly proportional to the peak intensity of m/z 323 ion, while the DNA breaking activity of fructosazine was much weaker than that of HCL-free D-glucosamine sample. 2,5-Dihydro-3,6-dimethylprazine and 2,3-dihydro-5,6-dimethylpyrazine having a dihydropyrazine skeleton the same as dihydrofructosazine showed the same extent of DNA strand breaking activity as did the HCL-free D-glucosamine sample. These results indicated that dihydrofructosazine produced during the dehydrochlorination is closely involved in the DNA breaking activity of HCL-free D-glucosamine sample.