Synthesis, structure and imaging of oligodeoxyribonucleotides with tellurium-nucleobase derivatization.
We report here the first synthesis of 5-phenyl-telluride-thymidine derivatives and the Te-phosphoramidite. We also report here the synthesis, structure and STM current-imaging studies of DNA oligonucleotides containing the nucleobases (thymine) derivatized with 5-phenyl-telluride functionality (5-Te). Our results show that the 5-Te-DNA is stable, and that the Te-DNA duplex has the thermo-stability similar to the corresponding native duplex. The crystal structure indicates that the 5-Te-DNA duplex structure is virtually identical to the native one, and that the Te-modified T and native A interact similarly to the native T and A pair. Furthermore, while the corresponding native showed weak signals, the DNA duplex modified with electron-rich tellurium functionality showed strong topographic and current peaks by STM imaging, suggesting a potential strategy to directly image DNA without structural perturbation.
Department of Chemistry, Georgia State University, Atlanta, GA 30303, USA.
Jia
J
Sheng
Abdalla E A
AE
Hassan
Wen
W
Zhang
Jianfeng
J
Zhou
Bingqian
B
Xu
Alexei S
AS
Soares
Zhen
Z
Huang
D018360:Crystallography, X-Ray; D004247:DNA / Q000648:ultrastructure; D016252:Microscopy, Scanning Tunneling; D008958:Models, Molecular; D009691:Nucleic Acid Denaturation; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000737:chemistry; D013691:Tellurium / Q000737:chemistry*; D013936:Thymidine / Q000031:analogs & derivatives*
D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D004247:DNA; D013691:Tellurium; D013936:Thymidine
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