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.
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 (1)H NMR scale in the presence of 100mM 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.
Institute of Organic Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Lodz, Poland.
Elzbieta
E
Sochacka
Paulina
P
Bartos
Karina
K
Kraszewska
Barbara
B
Nawrot
D000926:Anticodon / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D012343:RNA, Transfer / Q000737:chemistry*; D013455:Sulfur / Q000032:analysis*; D013891:Thiouridine / Q000031:analogs & derivatives* / Q000737:chemistry; D014529:Uridine / Q000737:chemistry
C105273:2-thiouridine; D000926:Anticodon; D013891:Thiouridine; D013455:Sulfur; D012343:RNA, Transfer; D006861:Hydrogen Peroxide; D014529:Uridine
2-Thiouridine; Desulfuration; Modified nucleoside; Oxidative stress; tRNA