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Conformation and Proton Configuration of Pyrimidine Deoxynucleoside Oxidation Damage Products in Water

La Francois, Christopher J. and Jang, Yun Hee and Çağin, Tahir and Goddard, William A., III and Sowers, Lawrence C. (2000) Conformation and Proton Configuration of Pyrimidine Deoxynucleoside Oxidation Damage Products in Water. Chemical Research in Toxicology, 13 (6). pp. 462-470. ISSN 0893-228X. http://resolver.caltech.edu/CaltechAUTHORS:20170808-103601650

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Abstract

Emerging data strongly suggest that the oxidation of DNA bases can contribute to genomic instability. Structural changes to DNA, induced by base oxidation, may reduce the fidelity of DNA replication and interfere with sequence-specific DNA−protein interactions. We have examined the structures of a series of pyrimidine deoxynucleoside oxidation damage products in aqueous solution. The modified nucleosides studied include the deoxynucleoside derivatives of 5-hydroxyuracil, 5-hydroxycytosine, 5-(hydroxymethyl)uracil, 5-(hydroxymethyl)cytosine, 5-formyluracil, and 5-formylcytosine. The influence of base oxidation on ionization constants, sugar conformation, and tautomeric configuration has been determined on the basis of UV, proton, and nitrogen NMR spectra of the ^(15)N-enriched derivatives. The potential biological consequences of the structural perturbations resulting from base oxidation are discussed.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/tx990209uDOIArticle
http://pubs.acs.org/doi/abs/10.1021/tx990209uPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/tx990209uPublisherSupporting Information
ORCID:
AuthorORCID
Çağin, Tahir0000-0002-3665-0932
Goddard, William A., III0000-0003-0097-5716
Additional Information:© 2000 American Chemical Society. Received December 20, 1999. Publication Date (Web): May 27, 2000. This work was supported in part by the National Institutes of Health [Grant GM41336 and Cancer Center Support Grant CA33572 (L.C.S.), Grant HD36385 (W.A.G.)]. In addition, the facilities of the MSC are also supported by DOE-ASCI, ARO-MURI, ARO-DURIP, the National Science Foundation Grant CHE-95-22179), Exxon Corp., Dow Chemical, 3M, Beckman Institute, Avery-Dennison, Chevron Corp., Seiko Epson, Asahi Chemical, and BP Amoco.
Funders:
Funding AgencyGrant Number
NIHGM41336
NIHCA33572
NIHHD36385
Department of Energy (DOE)UNSPECIFIED
Army Research Office (ARO)UNSPECIFIED
NSFCHE-95-22179
Exxon Corp.UNSPECIFIED
Dow Chemical CompanyUNSPECIFIED
3MUNSPECIFIED
Caltech Beckman InstituteUNSPECIFIED
Avery-DennisonUNSPECIFIED
Chevron Corp.UNSPECIFIED
Seiko EpsonUNSPECIFIED
Asahi ChemicalUNSPECIFIED
BP AmocoUNSPECIFIED
Record Number:CaltechAUTHORS:20170808-103601650
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20170808-103601650
Official Citation:Conformation and Proton Configuration of Pyrimidine Deoxynucleoside Oxidation Damage Products in Water Christopher J. La Francois, Yun Hee Jang, Tahir Cagin, William A. Goddard, III, and Lawrence C. Sowers Chemical Research in Toxicology 2000 13 (6), 462-470 DOI: 10.1021/tx990209u
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:79929
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:09 Aug 2017 19:25
Last Modified:09 Aug 2017 19:25

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