Abstract
The sequences CA'CGTG (where A' = 2-aminodeoxyadenosine) and m5CGCAm5CGTGCG are prepared and studied by IR, CD and 1H-NMR. Infrared spectra demonstrate the capacity of the modified hexamer and decamer to adopt a Z conformation. The influence of the NH2 substitution on the adenine or of the methylated terminal part of the decamer acting with the increase of the DNA concentration stabilizes the Z conformation at room temperature in low humidity films. Very weak proportion of Z conformation is detected in UV dilute solutions. In more concentrated NMR solutions, the Z proportion induced by high salt content is only 20-25%. The effects of the concentration and of the covalent modification of the bases are discussed.
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Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Behe M., Felsenfeld G. Effects of methylation on a synthetic polynucleotide: the B--Z transition in poly(dG-m5dC).poly(dG-m5dC). Proc Natl Acad Sci U S A. 1981 Mar;78(3):1619–1623. doi: 10.1073/pnas.78.3.1619. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Cavailles J. A., Neumann J. M., Taboury J., Langlois d'Estaintot B., Huynh-Dinh T., Igolen J., Tran-Dinh S. B,Z conformations and mechanism of the Z-B-coil transitions of the self-complementary deoxy-hexanucleotide d(C-G-m5C-G-C-G) by 1H-NMR and CD spectroscopy. J Biomol Struct Dyn. 1984 Jun;1(6):1347–1371. doi: 10.1080/07391102.1984.10507525. [DOI] [PubMed] [Google Scholar]
- Dickerson R. E., Drew H. R., Conner B. N., Wing R. M., Fratini A. V., Kopka M. L. The anatomy of A-, B-, and Z-DNA. Science. 1982 Apr 30;216(4545):475–485. doi: 10.1126/science.7071593. [DOI] [PubMed] [Google Scholar]
- Drew H. R., Dickerson R. E. Conformation and dynamics in a Z-DNA tetramer. J Mol Biol. 1981 Nov 15;152(4):723–736. doi: 10.1016/0022-2836(81)90124-8. [DOI] [PubMed] [Google Scholar]
- Drew H., Takano T., Tanaka S., Itakura K., Dickerson R. E. High-salt d(CpGpCpG), a left-handed Z' DNA double helix. Nature. 1980 Aug 7;286(5773):567–573. doi: 10.1038/286567a0. [DOI] [PubMed] [Google Scholar]
- Fujii S., Wang A. H., van der Marel G., van Boom J. H., Rich A. Molecular structure of (m5 dC-dG)3: the role of the methyl group on 5-methyl cytosine in stabilizing Z-DNA. Nucleic Acids Res. 1982 Dec 11;10(23):7879–7892. doi: 10.1093/nar/10.23.7879. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Gaffney B. L., Marky L. A., Jones R. A. The influence of the purine 2-amino group on DNA conformation and stability. Synthesis and conformational analysis of d[T(2-aminoA)]3. Nucleic Acids Res. 1982 Jul 24;10(14):4351–4361. doi: 10.1093/nar/10.14.4351. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Giessner-Prettre C., Pullman B., Tran-Dinh S., Neumann J. M., Huynh-Dinh T., Igolen J. Proton NMR study of the B----Z transition of d(CGm5CG)2 and d(CGm5CGCG)2: theory and experiment. Nucleic Acids Res. 1984 Apr 11;12(7):3271–3281. doi: 10.1093/nar/12.7.3271. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Hartmann B., Thuong N. T., Pouyet J., Ptak M., Leng M. Spectroscopic studies of (m5dC-dG)3: thermal stability of B- and Z-forms. Nucleic Acids Res. 1983 Jul 11;11(13):4453–4466. doi: 10.1093/nar/11.13.4453. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Howard F. B., Chen C. W., Cohen J. S., Miles H. T. Poly(d2NH2A-dT): effect of 2-amino substituent on the B to Z transition. Biochem Biophys Res Commun. 1984 Feb 14;118(3):848–853. doi: 10.1016/0006-291x(84)91472-4. [DOI] [PubMed] [Google Scholar]
- Kirnos M. D., Khudyakov I. Y., Alexandrushkina N. I., Vanyushin B. F. 2-aminoadenine is an adenine substituting for a base in S-2L cyanophage DNA. Nature. 1977 Nov 24;270(5635):369–370. doi: 10.1038/270369a0. [DOI] [PubMed] [Google Scholar]
- McIntosh L. P., Grieger I., Eckstein F., Zarling D. A., van de Sande J. H., Jovin T. M. Left-handed helical conformation of poly[d(A-m5C).d(G-T)]. Nature. 1983 Jul 7;304(5921):83–86. doi: 10.1038/304083a0. [DOI] [PubMed] [Google Scholar]
- Pilet J., Leng M. Comparison of poly(dG-dC).poly(dG-dC) conformations in oriented films and in solution. Proc Natl Acad Sci U S A. 1982 Jan;79(1):26–30. doi: 10.1073/pnas.79.1.26. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Pohl F. M., Jovin T. M. Salt-induced co-operative conformational change of a synthetic DNA: equilibrium and kinetic studies with poly (dG-dC). J Mol Biol. 1972 Jun 28;67(3):375–396. doi: 10.1016/0022-2836(72)90457-3. [DOI] [PubMed] [Google Scholar]
- Reese C. B., Ubasawa A. Nature of side-reactions in oligonucleotide synthesis involving arenesulphonyl derivatives of 3-nitro-1,2,4-triazole and related condensing agents. Nucleic Acids Symp Ser. 1980;(7):5–21. [PubMed] [Google Scholar]
- Taillandier E., Taboury J., Liquier J., Sautière P., Couppez M. Structural transitions in DNAs and nucleohistones studied by I.R. spectroscopy. Biochimie. 1981 Nov-Dec;63(11-12):895–898. doi: 10.1016/s0300-9084(82)80282-4. [DOI] [PubMed] [Google Scholar]
- Thamann T. J., Lord R. C., Wang A. H., Rich A. The high salt form of poly(dG-dC).poly(dG-dC) is left-handed Z-DNA: Raman spectra of crystals and solutions. Nucleic Acids Res. 1981 Oct 24;9(20):5443–5457. doi: 10.1093/nar/9.20.5443. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Tran-Dinh S., Neumann J. M., Taboury J., Huynh-Dinh T., Renous S., Genissel B., Igolen J. DNA fragment conformations. 1H-NMR comparative studies of helix-coil transition and conformation of d(C-A-C-G-T-G) and d(G-T-G-C-A-C). Influence of helix formation on proton chemical shifts. Eur J Biochem. 1983 Jul 1;133(3):579–589. doi: 10.1111/j.1432-1033.1983.tb07502.x. [DOI] [PubMed] [Google Scholar]
- Tran-Dinh S., Taboury J., Neumann J. M., Huynh-Dinh T., Genissel B., Langlois d'Estaintot B., Igolen J. 1H NMR and circular dichroism studies of the B and Z conformations of the self-complementary deoxyhexanucleotide d(m5C-G-C-G-m5-C-G): mechanism of the Z-B-coil transitions. Biochemistry. 1984 Mar 27;23(7):1362–1371. doi: 10.1021/bi00302a005. [DOI] [PubMed] [Google Scholar]
- Vincent-Fiquet O., Leflon P., Plaquet R., Biserte G. Caractérisation de l'activité L-thréonine désaminasique du foie de cobaye induite par un régime hyperprotidique. Biochimie. 1984 Jan;66(1):43–48. doi: 10.1016/0300-9084(84)90190-1. [DOI] [PubMed] [Google Scholar]
- Wang A. H., Quigley G. J., Kolpak F. J., Crawford J. L., van Boom J. H., van der Marel G., Rich A. Molecular structure of a left-handed double helical DNA fragment at atomic resolution. Nature. 1979 Dec 13;282(5740):680–686. doi: 10.1038/282680a0. [DOI] [PubMed] [Google Scholar]
- Wang A. J., Quigley G. J., Kolpak F. J., van der Marel G., van Boom J. H., Rich A. Left-handed double helical DNA: variations in the backbone conformation. Science. 1981 Jan 9;211(4478):171–176. doi: 10.1126/science.7444458. [DOI] [PubMed] [Google Scholar]