1mxj

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{{STRUCTURE_1mxj| PDB=1mxj | SCENE= }}
{{STRUCTURE_1mxj| PDB=1mxj | SCENE= }}
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'''NMR solution structure of benz[a]anthracene-dG in ras codon 12,2; GGCAGXTGGTG'''
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===NMR solution structure of benz[a]anthracene-dG in ras codon 12,2; GGCAGXTGGTG===
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==Overview==
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The conformation of the trans-anti-(1S,2R,3S,4R)-N(2)-[1-(1,2,3,4-tetrahydro-2,3,4-trihydroxybenz[ a]anthracenyl)]-2'-deoxyguanosyl adduct in d(G(1)G(2)C(3)A(4)G(5)X(6)T(7)G(8)G(9)T(10)G(11)).d(C(12)A(13)C(14)C(15)A( 16)C(17)C(18)T(19)G(20)C(21)C(22)), bearing codon 12 of the human N-ras protooncogene (underlined), was determined. This adduct had S stereochemistry at the benzylic carbon. Its occurrence in DNA is a consequence of trans opening by the deoxyguanosine amino group of (1R,2S,3S,4R)-1,2-epoxy-1,2,3,4-tetrahydrobenz[a]anthracenyl-3,4-diol. The resonance frequencies, relative to the unmodified DNA, of the X(6) H1' and H6 protons were shifted downfield, whereas those of the C(18) and T(19) H1', H2', H2' ', and H3' deoxyribose protons were shifted upfield. The imino and amino resonances exhibited the expected sequential connectivities, suggesting no interruption of Watson-Crick pairing. A total of 426 interproton distances, including nine uniquely assigned BA-DNA distances, were used in the restrained molecular dynamics calculations. The refined structure showed that the benz[a]anthracene moiety bound in the minor groove, in the 5'-direction from the modified site. This was similar to the (+)-trans-anti-benzo[a]pyrene-N(2)-dG adduct having S stereochemistry at the benzylic carbon [Cosman, M., De Los Santos, C., Fiala, R., Hingerty, B. E., Singh, S. B., Ibanez, V., Margulis, L. A., Live, D., Geacintov, N. E., Broyde, S., and Patel, D. J. (1992) Proc. Natl. Acad. Sci. U.S.A. 89, 1914-1918]. It differed from the (-)-trans-anti-benzo[c]phenanthrene-N(2)-dG adduct having S stereochemistry at the benzylic carbon, which intercalated in the 5'-direction [Lin, C. H., Huang, X., Kolbanovskii, A., Hingerty, B. E., Amin, S., Broyde, S., Geacintov, N. E., and Patel, D. J. (2001) J. Mol. Biol. 306, 1059-1080]. The results provided insight into how PAH molecular topology modulates adduct structure in duplex DNA.
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The line below this paragraph, {{ABSTRACT_PUBMED_12600200}}, adds the Publication Abstract to the page
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(as it appears on PubMed at http://www.pubmed.gov), where 12600200 is the PubMed ID number.
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{{ABSTRACT_PUBMED_12600200}}
==About this Structure==
==About this Structure==
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Full crystallographic information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=1MXJ OCA].
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Full experimental information is available from [http://oca.weizmann.ac.il/oca-bin/ocashort?id=1MXJ OCA].
==Reference==
==Reference==
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[[Category: B-like dna]]
[[Category: B-like dna]]
[[Category: Dna adduct]]
[[Category: Dna adduct]]
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''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Sat May 3 01:50:30 2008''
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''Page seeded by [http://oca.weizmann.ac.il/oca OCA ] on Mon Jul 28 17:11:35 2008''

Revision as of 14:11, 28 July 2008

Image:1mxj.png

Template:STRUCTURE 1mxj

NMR solution structure of benz[a]anthracene-dG in ras codon 12,2; GGCAGXTGGTG

Template:ABSTRACT PUBMED 12600200

About this Structure

Full experimental information is available from OCA.

Reference

Minor groove orientation for the (1S,2R,3S,4R)-N2- [1-(1,2,3,4-tetrahydro-2,3,4-trihydroxybenz[a]anthracenyl)]-2'-deoxyguanos yl adduct in the N-ras codon 12 sequence., Kim HY, Wilkinson AS, Harris CM, Harris TM, Stone MP, Biochemistry. 2003 Mar 4;42(8):2328-38. PMID:12600200

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