Abstract
The influence of the amino group of guanine on the molecular electrostatic potential and the accessibility to reactive sites of B-DNA is investigated by comparing the two model double helices poly (dI.dC) and poly (dG.dC). The calculations clarify the “disruptive” role of the guanine amino group on nucleic acid-polypeptide interactions.
Full text
PDF![7041](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2e9/327660/4850e9e84c8d/nar00417-0391.png)
![7042](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2e9/327660/e12143379919/nar00417-0392.png)
![7043](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2e9/327660/adfe6cd921da/nar00417-0393.png)
![7044](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2e9/327660/c2556b1e5c15/nar00417-0394.png)
![7045](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2e9/327660/1cf4b4f491bd/nar00417-0395.png)
![7046](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2e9/327660/d6c4c8437924/nar00417-0396.png)
![7047](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2e9/327660/237cd4730316/nar00417-0397.png)
![7048](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2e9/327660/1840d2e6af9b/nar00417-0398.png)
![7049](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2e9/327660/21a30d7bf16b/nar00417-0399.png)
![7050](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2e9/327660/d79f80c39b1a/nar00417-0400.png)
![7051](https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f2e9/327660/3fc9327c7190/nar00417-0401.png)
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Arnott S., Hukins D. W. Optimised parameters for A-DNA and B-DNA. Biochem Biophys Res Commun. 1972 Jun 28;47(6):1504–1509. doi: 10.1016/0006-291X(72)90243-4. [DOI] [PubMed] [Google Scholar]
- Drinkwater N. R., Miller J. A., Miller E. C., Yang N. C. Covalent intercalative binding to DNA in relation to the mutagenicity of hydrocarbon epoxides and N-acetoxy-2-acetylaminofluorene. Cancer Res. 1978 Oct;38(10):3247–3255. [PubMed] [Google Scholar]
- Hurley L. H., Petrusek R. Proposed structure of the anthramycin-DNA adduct. Nature. 1979 Nov 29;282(5738):529–531. doi: 10.1038/282529a0. [DOI] [PubMed] [Google Scholar]
- Jeffrey A. M., Jennette K. W., Blobstein S. H., Weinstein I. B., Beland F. A., Harvey R. G., Kasal H., Miura I., Nakanishi K. Letter: Benzo[a]pyrene-nucleic acid derivative found in vivo: structure of a benzo[a]pyrenetetrahydrodiol epoxide-guanosine adduct. J Am Chem Soc. 1976 Sep 1;98(18):5714–5715. doi: 10.1021/ja00434a060. [DOI] [PubMed] [Google Scholar]
- Jennette K. W., Jeffrey A. M., Blobstein S. H., Beland F. A., Harvey R. G., Weinstein I. B. Nucleoside adducts from the in vitro reaction of benzo[a]pyrene-7,8-dihydrodiol 9,10-oxide or benzo[a]pyrene 4,5-oxide with nucleic acids. Biochemistry. 1977 Mar 8;16(5):932–938. doi: 10.1021/bi00624a019. [DOI] [PubMed] [Google Scholar]
- Krylov A. S., Grokhovsky S. L., Zasedatelev A. S., Zhuze A. L., Gursky G. V., Gottikh B. P. Quantitative estimation of the contribution of pyrrolcarboxamide groups of the antibiotic distamycin A into specificity of its binding to DNA AT pairs. Nucleic Acids Res. 1979 Jan;6(1):289–304. doi: 10.1093/nar/6.1.289. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Lavery J. P. Teratology for the dermatologist. Int J Dermatol. 1981 May;20(4):272–274. doi: 10.1111/j.1365-4362.1981.tb04336.x. [DOI] [PubMed] [Google Scholar]
- Lavery R., Pullman A., Pullman B., de Oliveira M. The electrostatic molecular potential of tRNAPhe. IV. The potentials and steric accessibilities of sites associated with the bases. Nucleic Acids Res. 1980 Nov 11;8(21):5095–5111. doi: 10.1093/nar/8.21.5095. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Maruyama I. N., Tanaka N., Kondo S., Umezawa H. Structure of a neothramycin-2'-deoxyguanosine adduct. Biochem Biophys Res Commun. 1981 Feb 27;98(4):970–975. doi: 10.1016/0006-291x(81)91205-5. [DOI] [PubMed] [Google Scholar]
- Poirier M. C., Yuspa S. H., Weinstein I. B., Blobstein S. Detection of carcinogen-DNA adducts by radiommunoassay. Nature. 1977 Nov 10;270(5633):186–188. doi: 10.1038/270186a0. [DOI] [PubMed] [Google Scholar]
- Pullman B., Perahia D., Cauchy D. The molecular electrostatic potential of the B-DNA helix. VI. The regions of the base pairs in poly (dG.dC) and poly (dA.dT). Nucleic Acids Res. 1979 Aug 24;6(12):3821–3829. doi: 10.1093/nar/6.12.3821. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Seeman N. C., Rosenberg J. M., Rich A. Sequence-specific recognition of double helical nucleic acids by proteins. Proc Natl Acad Sci U S A. 1976 Mar;73(3):804–808. doi: 10.1073/pnas.73.3.804. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Weinstein I. B., Jeffrey A. M., Jennette K. W., Blobstein S. H., Harvey R. G., Harris C., Autrup H., Kasai H., Nakanishi K. Benzo(a)pyrene diol epoxides as intermediates in nucleic acid binding in vitro and in vivo. Science. 1976 Aug 13;193(4253):592–595. doi: 10.1126/science.959820. [DOI] [PubMed] [Google Scholar]
- Wähnert U., Zimmer O., Luck G., Pitra O. (dA-dT) dependent inactivation of the DNA template properties by interaction with netropsin and distamycin A. Nucleic Acids Res. 1975 Mar;2(3):391–404. doi: 10.1093/nar/2.3.391. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Yamasaki H., Pulkrabek P., Grunberger D., Weinstein I. B. Differential excision from DNA of the C-8 and N2 guanosine adducts of N-acetyl-2-aminofluorene by single strand-specific endonucleases. Cancer Res. 1977 Oct;37(10):3756–3760. [PubMed] [Google Scholar]
- Zimmer C. Effects of the antibiotics netropsin and distamycin A on the structure and function of nucleic acids. Prog Nucleic Acid Res Mol Biol. 1975;15(0):285–318. doi: 10.1016/s0079-6603(08)60122-1. [DOI] [PubMed] [Google Scholar]