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Solution structure of an intramolecular DNA triplex containing an N^7-glycosylated guanine which mimics a protonated cytosine

Koshlap, Karl M. and Schultze, Peter and Brunar, Helmut and Dervan, Peter B. and Feigon, Juli (1997) Solution structure of an intramolecular DNA triplex containing an N^7-glycosylated guanine which mimics a protonated cytosine. Biochemistry, 36 (9). pp. 2659-2668. ISSN 0006-2960. https://resolver.caltech.edu/CaltechAUTHORS:20160510-102100483

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Abstract

The three-dimensional structure of a pyrimidine-purine-pyrimidine DNA triplex containing an N^7-glycosylated guanine (^7G) in the third strand has been determined by NMR spectroscopy, restrained molecular dynamics calculations, and complete relaxation matrix refinement. Glycosylation of the guanine at the N^7 position permits it to adopt a conformation such that the Hoogsteen face of the base mimics the arrangement of hydrogen bond donors seen in protonated cytosine. The NMR data confirm the previously proposed hydrogen bonding scheme of the ^7G·G·C triplet. The three-dimensional structure of the triplex accommodates the ^7G with less distortion of the phosphodiester backbone than would be required for an N^9-glycosylated guanine in the same sequence position, but some changes in the positions of the phosphodiester backbone are present compared to a C^+·G·C triplet. The structure provides a rationale for the observations that ^7G binds to Watson-Crick G·C base pairs with higher specificity and affinity than guanine, but with a lower stability at pH 5.2 than would be provided by a canonical C^+·G·C triplet.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/bi962438aDOIArticle
http://pubs.acs.org/doi/abs/10.1021/bi962438aPublisherArticle
ORCID:
AuthorORCID
Dervan, Peter B.0000-0001-8852-7306
Additional Information:© 1997 American Chemical Society. Received September 27, 1996; Revised Manuscript Received November 26, 1996. This work was supported by NIH Grant GM 37254 to J.F. and ONR Grant N00014-95-1075 to P.B.D.
Funders:
Funding AgencyGrant Number
NIHGM-37254
Office of Naval Research (ONR)N00014-95-1075
Issue or Number:9
Record Number:CaltechAUTHORS:20160510-102100483
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20160510-102100483
Official Citation:Solution Structure of an Intramolecular DNA Triplex Containing an N7-Glycosylated Guanine Which Mimics a Protonated Cytosine, Karl M. Koshlap, Peter Schultze, Helmut Brunar, Peter B. Dervan, and Juli Feigon Biochemistry 1997 36 (9), 2659-2668 DOI: 10.1021/bi962438a
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:66881
Collection:CaltechAUTHORS
Deposited By: Victoria Brennan
Deposited On:18 May 2016 19:21
Last Modified:26 Nov 2019 11:15

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