Systematic assignment of NMR spectra of 5-substituted-4-thiopyrimidine nucleosides

• Autor: Zhang, Xiaohui ; Wang, Jian ; Xu, Yao-Zhong
• Assuntos: 13C ; 4-thiothymidine ; 4-thiouridine ; 5-bromo-4-thiouridine ; 5-substituted pyrimidine ; DNA ; Magnetic Resonance Spectroscopy - standards ; NMR ; nucleoside ; Pyrimidine Nucleosides - chemical synthesis ; Pyrimidine Nucleosides - chemistry ; Reference Standards ; RNA
• É parte de: Magnetic resonance in chemistry, 2013-09, Vol.51 (9), p.523-529
• Notas: ArticleID:MRC3980
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• Descrição: Unambiguous characterization of 5‐substituted‐4‐thiopyrimidine nucleosides (ribonucleosides and 2'‐deoxynucleosides) was performed using NMR spectroscopy. Assignments of all proton and carbon signals of 5‐bromo‐4‐thiouridine and related nucleosides were systematically carried out and firmly established by COSY and HMQC techniques. The NMR data of various 4‐thiopyrimidine nucleosides are compared, and the key contributing factors discussed. The approach presented here is applicable to other modified nucleosides and nucleotides, as well as nucleobases. Copyright © 2013 John Wiley & Sons, Ltd. A series of 5‐substituted‐4‐thio‐uridines and their 2'‐deoxy analogues have been successfully prepared. Their 1H and 13C NMR have been systemically investigated and discussed together with other base‐modified nucleosides. The imino proton in these 4‐thionucleosides has an unusually high chemical shift and can serve as an excellent marker in NMR studies of nucleic acids containing these thio‐bases.
  
• Editor: England: Blackwell Publishing Ltd
  
• Idioma: Inglês