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. 1987 Apr 10;15(7):3059–3072. doi: 10.1093/nar/15.7.3059

Minor-groove-modified oligonucleotides: synthesis of decadeoxynucleotides containing hypoxanthine, N2-methylguanine and 3-deazaadenine, and their interactions with restriction endonucleases Bgl II, Sau, 3AI, and Mbo I (Nucleosides and Nucleotides Part 75).

A Ono, T Ueda
PMCID: PMC340715  PMID: 3031618

Abstract

Decadeoxynucleotides containing hypoxanthine, N2-methylguanine, 3-deazaadenine in the recognition sequences of restriction endonucleases Bgl II, Sau 3AI, and Mbo I were synthesized. These decanucleotides modified in the base moieties facing in to the minor groove were strongly resistant to hydrolysis by Bgl II and partially resistant to that of Sau 3AI and Mbo I. The decadeoxynucleotide containing 3-deazaadenine in place of adenine was bound to Bgl II strongly, whereas the nucleotides containing hypoxanthine and N2-methylguanine were bound less tightly.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Broka C., Hozumi T., Arentzen R., Itakura K. Simplications in the synthesis of short oligonucleotide blocks. Nucleic Acids Res. 1980 Nov 25;8(22):5461–5471. doi: 10.1093/nar/8.22.5461. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Butkus V., Klimasauskas S., Kersulyte D., Vaitkevicius D., Lebionka A., Janulaitis A. Investigation of restriction-modification enzymes from M. varians RFL19 with a new type of specificity toward modification of substrate. Nucleic Acids Res. 1985 Aug 26;13(16):5727–5746. doi: 10.1093/nar/13.16.5727. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Duncan C. H., Wilson G. A., Young F. E. Biochemical and genetic properties of site-specific restriction endonucleases in Bacillus globigii. J Bacteriol. 1978 Apr;134(1):338–344. doi: 10.1128/jb.134.1.338-344.1978. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Dwyer-Hallquist P., Kézdy F. J., Agarwal K. L. Interaction of the HpaI endonuclease with synthetic oligonucleotides. Biochemistry. 1982 Sep 14;21(19):4693–4700. doi: 10.1021/bi00262a027. [DOI] [PubMed] [Google Scholar]
  5. Ehrlich M., Gama-Sosa M. A., Carreira L. H., Ljungdahl L. G., Kuo K. C., Gehrke C. W. DNA methylation in thermophilic bacteria: N4-methylcytosine, 5-methylcytosine, and N6-methyladenine. Nucleic Acids Res. 1985 Feb 25;13(4):1399–1412. doi: 10.1093/nar/13.4.1399. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Ehrlich M., Wang R. Y. 5-Methylcytosine in eukaryotic DNA. Science. 1981 Jun 19;212(4501):1350–1357. doi: 10.1126/science.6262918. [DOI] [PubMed] [Google Scholar]
  7. Frederick C. A., Grable J., Melia M., Samudzi C., Jen-Jacobson L., Wang B. C., Greene P., Boyer H. W., Rosenberg J. M. Kinked DNA in crystalline complex with EcoRI endonuclease. Nature. 1984 May 24;309(5966):327–331. doi: 10.1038/309327a0. [DOI] [PubMed] [Google Scholar]
  8. Gelinas R. E., Myers P. A., Roberts R. J. Two sequence-specific endonucleases from Moraxella bovis. J Mol Biol. 1977 Jul;114(1):169–179. doi: 10.1016/0022-2836(77)90290-x. [DOI] [PubMed] [Google Scholar]
  9. Jay E., Bambara R., Padmanabhan R., Wu R. DNA sequence analysis: a general, simple and rapid method for sequencing large oligodeoxyribonucleotide fragments by mapping. Nucleic Acids Res. 1974 Mar;1(3):331–353. doi: 10.1093/nar/1.3.331. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Lu A. L., Jack W. E., Modrich P. DNA determinants important in sequence recognition by Eco RI endonuclease. J Biol Chem. 1981 Dec 25;256(24):13200–13206. [PubMed] [Google Scholar]
  11. Miyoshi K., Arentzen R., Huang T., Itakura K. Solid-phase synthesis of polynucleotides. IV. Usage of polystyrene resins for the synthesis of polydeoxyribonucleotides by the phosphostriester method. Nucleic Acids Res. 1980 Nov 25;8(22):5507–5517. doi: 10.1093/nar/8.22.5507. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Mizuno Y., Kitano S., Nomura A. Nucleotides. VI. Syntheses and spectral properties of some deazaadenylyl-deazaadenosines (dinucleoside monophosphates with unusual CD-spectrum) and closely related dinucleoside monophosphates. Nucleic Acids Res. 1975 Dec;2(12):2193–2207. doi: 10.1093/nar/2.12.2193. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Modrich P., Rubin R. A. Role of the 2-amino group of deoxyguanosine in sequence recognition by EcoRI restriction and modification enzymes. J Biol Chem. 1977 Oct 25;252(20):7273–7278. [PubMed] [Google Scholar]
  14. Ono A., Sato M., Ohtani Y., Ueda T. Synthesis of deoxyoligonucleotides containing 7-deazaadenine: recognition and cleavage by restriction endonuclease Bgl II and Sau 3AI (nucleosides and nucleotides Part 55). Nucleic Acids Res. 1984 Dec 11;12(23):8939–8949. doi: 10.1093/nar/12.23.8939. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Ono A., Ueda T. Synthesis of decadeoxyribonucleotides containing N6-methyladenine, N4-methylcytosine, and 5-methylcytosine: recognition and cleavage by restriction endonucleases (nucleosides and nucleotides part 74). Nucleic Acids Res. 1987 Jan 12;15(1):219–232. doi: 10.1093/nar/15.1.219. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. 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]
  17. Silberklang M., Gillum A. M., RajBhandary U. L. The use of nuclease P1 in sequence analysis of end group labeled RNA. Nucleic Acids Res. 1977 Dec;4(12):4091–4108. doi: 10.1093/nar/4.12.4091. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Sussenbach J. S., Monfoort C. H., Schiphof R., Stobberingh E. E. A restriction endonuclease from Staphylococcus aureus. Nucleic Acids Res. 1976 Nov;3(11):3193–3202. doi: 10.1093/nar/3.11.3193. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. Wolfes H., Fliess A., Pingoud A. A comparison of the structural requirements for DNA cleavage by the isoschizomers HaeIII, BspRI and BsuRI. Eur J Biochem. 1985 Jul 1;150(1):105–110. doi: 10.1111/j.1432-1033.1985.tb08994.x. [DOI] [PubMed] [Google Scholar]

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