A Caltech Library Service

Coupling into the Base Pair Stack Is Necessary for DNA-Mediated Electrochemistry

Gorodetsky, Alon A. and Green, Omar and Yavin, Eylon and Barton, Jacqueline K. (2007) Coupling into the Base Pair Stack Is Necessary for DNA-Mediated Electrochemistry. Bioconjugate Chemistry, 18 (5). pp. 1434-1441. ISSN 1043-1802. doi:10.1021/bc0700483.

[img] PDF - Supplemental Material
See Usage Policy.

[img] PDF - Supplemental Material
See Usage Policy.


Use this Persistent URL to link to this item:


The electrochemistry of DNA films modified with different redox probes linked to DNA through saturated and conjugated tethers was investigated. Experiments feature two redox probes bound to DNA on two surfaces:  anthraquinone (AQ)-modified uridines incorporated into thiolated DNA on gold (Au) and 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMPO)-modified uridines in pyrene-labeled DNA on highly oriented pyrolytic graphite (HOPG). The electrochemistry of these labels when incorporated into DNA has been examined in DNA films containing both well matched and mismatched DNA. DNA-mediated electrochemistry is found to be effective for the TEMPO probe linked with an acetylene linker but not for a saturated TEMPO connected through an ethylenediamine linker. For the AQ probe, DNA-mediated electrochemistry is found with an acetylene linker to uridine but not with an alkyl chain to the 5‘ terminus of the oligonucleotide. Large electrochemical signals and effective discrimination of intervening base mismatches are achieved for the probes connected through the acetylene linkages, while probes connected through saturated linkages exhibit small electrochemical signals associated only with direct surface to probe charge transfer and poor mismatch discrimination. Thus DNA electrochemistry with these probes is dramatically influenced by the chemical nature of their linkage to DNA. These results highlight the importance of effective coupling into the π-stack for long-range DNA-mediated electrochemistry.

Item Type:Article
Related URLs:
URLURL TypeDescription Information
Gorodetsky, Alon A.0000-0002-3811-552X
Barton, Jacqueline K.0000-0001-9883-1600
Additional Information:© 2007 American Chemical Society. February 12, 2007; Revised Manuscript Received April 24, 2007. Publication Date (Web): June 20, 2007. We thank the National Institutes of Health (GM61077) for their financial support of this research. Figure S1 contains AFM characterization of DNA modified and bare HOPG. Figure S2 shows melting point determinations of DNA modified with ethynylanthraquinone and unmodified DNA composed of the same sequence. Figure S3 shows the correlation of the current displayed by DNA modified with ethynylanthraquinone as a function of scan rate. Figure S4 shows the peak splitting as compared to the log of scan rate.
Funding AgencyGrant Number
Issue or Number:5
Record Number:CaltechAUTHORS:20160229-103205895
Persistent URL:
Official Citation:Coupling into the Base Pair Stack Is Necessary for DNA-Mediated Electrochemistry Alon A. Gorodetsky, Omar Green, Eylon Yavin, and Jacqueline K. Barton Bioconjugate Chemistry 2007 18 (5), 1434-1441 DOI: 10.1021/bc0700483
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:64843
Deposited By: Ruth Sustaita
Deposited On:29 Feb 2016 19:15
Last Modified:10 Nov 2021 23:36

Repository Staff Only: item control page