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Thieme Chemistry Journal Awardees - Where Are They Now? Synthesis and Optical Properties of Nile Red Modified 2 '-Deoxyuridine and 7-Deaza-2 '-deoxyadenosine: Highly Emissive Solvatochromic Nucleosides

  作者 VARGHESE REJI; GAJULA PRAVEEN KUMAR; CHAKRABORTY TUSHAR KANTI; WAGENKNECHT HANSACHIM  
  选自 期刊  SYNLETT;  卷期  2009年-20;  页码  3252-3257  
  关联知识点  
 

[摘要]A general synthetic strategy for the attachment of Nile red through a rigid acetylene linker to 2'-deoxyuridine and 7-deaza-2'-deoxyadenosine using Sonogashira coupling is demonstrated. Protection of either 5'-OH or N-7 of the nucleosides increased the yields of the cross-couplings significantly. Both Nile red modified 2'-deoxyuridine and 7-deaza-2'-deoxyadenosine as well as their derivatives exhibit excellent fluorescence quantum efficiencies and positive solvatochromism. The incorporation of the Nile red modified 2'-deoxyuridine into oligonucleotides yields bright fluorescent probes with maintained canonical base pairing in DNA.

 
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