37085-48-6Relevant articles and documents
A novel synthesis of 3'-deoxy-3'-nitrothymidine via nucleophilic substitution with nitrite anion
Huang,Ragouzeos,Rideout
, p. 691 - 695 (1995)
Nucleophilic substitution at C3' of 1-(2-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)-2-methoxy-5-methyl- 4(1H)-pyrimidinone (5) with methyl iodide/triphenylphosphine/diethyl azodicarboxylate gave the expected inverted iodide 6 and minor epimer 7. Treatment of 6 with lithium nitrite/phloroglucinol yielded the desired nitro derivative 8 and subsequent acidic deprotection afforded the title compound 1. This represents a novel method for the introduction of a nitro group into the furanosyl moiety of a nucleoside. The nmr spectroscopic techniques (COSY, NOESY, nOe, HMQC and HMBC) were used to determine the stereochemistry at C3' of the nucleosides. Spectral analysis of H-D exchange at the 3'-position of 1 did not indicate the formation of its epimer 10.
Syntheses and characterizations of the in vivo replicative bypass and mutagenic properties of the minor-groove O2-alkylthymidine lesions
Zhai, Qianqian,Wang, Pengcheng,Cai, Qian,Wang, Yinsheng
, p. 10529 - 10537 (2015/01/30)
Endogenous metabolism, environmental exposure, and treatment with some chemotherapeutic agents can all give rise to DNA alkylation, which can occur on the phosphate backbone as well as the ring nitrogen or exocyclic nitrogen and oxygen atoms of nucleobases. Previous studies showed that the minor-groove O2-alkylated thymidine (O2-alkyldT) lesions are poorly repaired and persist in mammalian tissues. In the present study, we synthesized oligodeoxyribonucleotides harboring seven O2-alkyldT lesions, with the alkyl group being a Me, Et, nPr, iPr, nBu, iBu or sBu, at a defined site and examined the impact of these lesions on DNA replication in Escherichia coli cells. Our results demonstrated that the replication bypass efficiencies of the O2-alkyldT lesions decreased with the chain length of the alkyl group, and these lesions directed promiscuous nucleotide misincorporation in E. coli cells. We also found that deficiency in Pol V, but not Pol II or Pol IV, led to a marked drop in bypass efficiencies for most O2-alkyldT lesions. We further showed that both Pol IV and Pol V were essential for the misincorporation of dCMP opposite these minor-groove DNA lesions, whereas only Pol V was indispensable for the T→A transversion introduced by these lesions. Depletion of Pol II, however, did not lead to any detectable alterations in mutation frequencies for any of the O2-alkyldT lesions. Thus, our study provided important new knowledge about the cytotoxic and mutagenic properties of the O2-alkyldT lesions and revealed the roles of the SOS-induced DNA polymerases in bypassing these lesions in E. coli cells.
Method for preparing radiolabeled thymidine
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Sheet 3/3, (2008/06/13)
The invention is a novel method and precursor for preparing radiolabeled nucleosides. In particular, the invention is useful for preparing 3′-[18F]fluorothymidine. The method uses an enol group that is attached to the 2-position on the pyrimidi
Oligodeoxynucleotidesd containing O2-alkylthymine: Synthesis and characterization
Xu,Swann
, p. 303 - 306 (2007/10/02)
Simple procedures for preparation of O2-alkylthymidines and of their phosphoramidite monomers (IV) are described. These monomers have been successfully incorporated into DNA oligomers. The measurements of the melting temperature (Tm) of DNA dup
