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...

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Main Authors:	Sheng, Jia, Hassan, Abdalla E. A., Zhang, Wen, Zhou, Jianfeng, Xu, Bingqian, Soares, Alexei S., Huang, Zhen
Format:	Online
Language:	English
Published:	Oxford University Press 2011
Online Access:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3089452/

id	pubmed-3089452
recordtype	oai_dc
spelling	pubmed-30894522011-05-09 Synthesis, structure and imaging of oligodeoxyribonucleotides with tellurium-nucleobase derivatization Sheng, Jia Hassan, Abdalla E. A. Zhang, Wen Zhou, Jianfeng Xu, Bingqian Soares, Alexei S. Huang, Zhen Synthetic Biology and Chemistry 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. Oxford University Press 2011-05 2011-01-17 /pmc/articles/PMC3089452/ /pubmed/21245037 http://dx.doi.org/10.1093/nar/gkq1288 Text en © The Author(s) 2011. Published by Oxford University Press. http://creativecommons.org/licenses/by-nc/2.5 This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/2.5), which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.
repository_type	Open Access Journal
institution_category	Foreign Institution
institution	US National Center for Biotechnology Information
building	NCBI PubMed
collection	Online Access
language	English
format	Online
author	Sheng, Jia Hassan, Abdalla E. A. Zhang, Wen Zhou, Jianfeng Xu, Bingqian Soares, Alexei S. Huang, Zhen
spellingShingle	Sheng, Jia Hassan, Abdalla E. A. Zhang, Wen Zhou, Jianfeng Xu, Bingqian Soares, Alexei S. Huang, Zhen Synthesis, structure and imaging of oligodeoxyribonucleotides with tellurium-nucleobase derivatization
author_facet	Sheng, Jia Hassan, Abdalla E. A. Zhang, Wen Zhou, Jianfeng Xu, Bingqian Soares, Alexei S. Huang, Zhen
author_sort	Sheng, Jia
title	Synthesis, structure and imaging of oligodeoxyribonucleotides with tellurium-nucleobase derivatization
title_short	Synthesis, structure and imaging of oligodeoxyribonucleotides with tellurium-nucleobase derivatization
title_full	Synthesis, structure and imaging of oligodeoxyribonucleotides with tellurium-nucleobase derivatization
title_fullStr	Synthesis, structure and imaging of oligodeoxyribonucleotides with tellurium-nucleobase derivatization
title_full_unstemmed	Synthesis, structure and imaging of oligodeoxyribonucleotides with tellurium-nucleobase derivatization
title_sort	synthesis, structure and imaging of oligodeoxyribonucleotides with tellurium-nucleobase derivatization
description	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.
publisher	Oxford University Press
publishDate	2011
url	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3089452/
_version_	1611452446667702272

Synthesis, structure and imaging of oligodeoxyribonucleotides with tellurium-nucleobase derivatization

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