Desulfuration of 2-thiouridine with hydrogen peroxide in the physiological pH range 6.6-7.6 is pH-dependent and results in two distinct products

被引：28
作者：
Sochacka, Elzbieta [1 ]
Bartos, Paulina [1 ]
Kraszewska, Karina [2 ]
Nawrot, Barbara [2 ]
机构：
[1] Lodz Univ Technol, Inst Organ Chem, PL-90924 Lodz, Poland
[2] Polish Acad Sci, Ctr Mol & Macromol Studies, PL-90363 Lodz, Poland
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2013年 / 23卷 / 21期
关键词：
2-Thiouridine; tRNA; Modified nucleoside; Oxidative stress; Desulfuration; TRANSFER-RNA; ANTICODON; OXIDATION; 2-THIORIBOTHYMIDINE; DESULFURIZATION; NUCLEOSIDES; DERIVATIVES; CHEMISTRY; CLEAVAGE;
D O I：
10.1016/j.bmcl.2013.08.114
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The 2-thiomodified nucleosides, located at first position of tRNAs anticodon, may constitute a primary target for oxidative attack under conditions of oxidative stress. Desulfuration of 2-thiouridine (S2U) was investigated in the H-1 NMR scale in the presence of 100 mM H2O2 and phosphate buffer in the physiological pH range, from pH 6.6 to 7.6. The obtained data demonstrate an intriguing result that within one unit of the pH range uridine is the major product of the S2U desulfuration in the pH 7.6, while the 4-pyrimidinone nucleoside (H2U) is dominant in pH 6.6. The possible desulfuration pathway and the biological importance of the transformation of S2U either to U or H2U are discussed in the context of the tRNA oxidative damage. (c) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5803 / 5805
页数：3
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