Fabrication of ssDNA/Oligo(ethylene glycol) Monolayers by Promoted Exchange Reaction with Thiol and Disulfide Substituents

Fabrication of ssDNA/Oligo(ethylene glycol) Monolayers by Promoted Exchange Reaction with Thiol and Disulfide Substituents

Biorepulsive oligo(ethylene glycol)-substituted alkanethiolate (OEG-AT) monolayers on gold can serve as primary templates for promoted (by electron irradiation) exchange reaction with thiolated ssDNA species, resulting in the formation of mixed OEG-AT/ssDNA monolayers of desired composition. Here we...

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Veröffentlicht in:Journal of physical chemistry. C 2014-02, Vol.118 (6), p.3093-3101
Hauptverfasser: Khan, M. Nuruzzaman, Zharnikov, Michael
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Zharnikov, Michael
description Biorepulsive oligo(ethylene glycol)-substituted alkanethiolate (OEG-AT) monolayers on gold can serve as primary templates for promoted (by electron irradiation) exchange reaction with thiolated ssDNA species, resulting in the formation of mixed OEG-AT/ssDNA monolayers of desired composition. Here we test the ability of alternative, disulfide precursors to serve as substituents in such a reaction. Two representative molecules, based on adenine-based homo-oligonucleotide (25-mer), were used, viz., asymmetric disulfide with a short second chain (A25SSOH) and symmetric disulfide (A25SSA25). The results were compared to the reference system of thiolated ssDNA (A25SH). Both disulfide precursors were found to be suitable for the reaction, further extending the types of commercially available compounds which can be used for this approach. A25SSOH exhibited quite high efficiency, similar to A25SH, while the efficiency of A25SSA25 was noticeably lower, especially at low irradiation doses (
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A25SSOH exhibited quite high efficiency, similar to A25SH, while the efficiency of A25SSA25 was noticeably lower, especially at low irradiation doses (&lt;0.6 mC/cm2). Also, the single component, A25SSA25-based ssDNA monolayer, was of lower quality as compared to the films prepared from the A25SH and A25SSOH precursors. The above observations were explained by the bulky character and conformational flexibility of A25SSA25, which hinder the proper assembly and efficient exchange reaction.</description><identifier>ISSN: 1932-7447</identifier><identifier>EISSN: 1932-7455</identifier><identifier>DOI: 10.1021/jp411353f</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Journal of physical chemistry. 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Here we test the ability of alternative, disulfide precursors to serve as substituents in such a reaction. Two representative molecules, based on adenine-based homo-oligonucleotide (25-mer), were used, viz., asymmetric disulfide with a short second chain (A25SSOH) and symmetric disulfide (A25SSA25). The results were compared to the reference system of thiolated ssDNA (A25SH). Both disulfide precursors were found to be suitable for the reaction, further extending the types of commercially available compounds which can be used for this approach. A25SSOH exhibited quite high efficiency, similar to A25SH, while the efficiency of A25SSA25 was noticeably lower, especially at low irradiation doses (&lt;0.6 mC/cm2). Also, the single component, A25SSA25-based ssDNA monolayer, was of lower quality as compared to the films prepared from the A25SH and A25SSOH precursors. The above observations were explained by the bulky character and conformational flexibility of A25SSA25, which hinder the proper assembly and efficient exchange reaction.</abstract><pub>American Chemical Society</pub><doi>10.1021/jp411353f</doi><tpages>9</tpages></addata></record>
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title Fabrication of ssDNA/Oligo(ethylene glycol) Monolayers by Promoted Exchange Reaction with Thiol and Disulfide Substituents
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