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. 1975 Dec;2(12):2193–2207. doi: 10.1093/nar/2.12.2193

Nucleotides. VI. Syntheses and spectral properties of some deazaadenylyl-deazaadenosines (dinucleoside monophosphates with unusual CD-spectrum) and closely related dinucleoside monophosphates.

Y Mizuno, S Kitano, A Nomura
PMCID: PMC343588  PMID: 1052539

Abstract

Nine dinucleoside phosphates containing 1-deaza-(1A) and 3-deazaadenosine (3A) were prepared. Hypochromicity and CD spectra of these dimers were determined. It was found that varying degrees of base-stacking are operative with these oligonucleotides and their CD spectra fall into three classes. The first class CD spectra which are more or less similar in profile to those of adenylyl-(3'-5')-adenosine includes the CD spectra of 1A2'p5'A, 1A3'p5A, 3A2'p5'A and 3A3'p5'A. The second class includes the CD spectra of A2'p5'1A and A3'p5'1A whose characteristic is that the positive Cotton band appears in the range of 280-310 nm. The third type CD spectra has the characteristics that the negative Cotton band appears in the longer wavelength region and th CD spectra are similar in profile to those of L-adenylyl-(3'-5')-L-adenosine which has the "left-handed helical" conformation. The CD spectra of A2'p5'3A, A3'p5'3A and 3A3'p5'A belong to this class. Another salient observation emerging from the CD-determination is that 3A3'p5'3A has the spectrum quite different from that of poly 3-deazaadenylic acid.

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Selected References

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  1. Brahms J., Michelson A. M., Van Holde K. E. Adenylate oligomers in single- and double-strand conformation. J Mol Biol. 1966 Feb;15(2):467–488. doi: 10.1016/s0022-2836(66)80122-5. [DOI] [PubMed] [Google Scholar]
  2. Hagenberg L., Gassen H. G., Matthaei H. Synthesis and coding properties of poly(c 1 A), poly(c 3 A), poly(c 7 A) and poly(h 6 A). Biochem Biophys Res Commun. 1973 Feb 20;50(4):1104–1112. doi: 10.1016/0006-291x(73)91520-9. [DOI] [PubMed] [Google Scholar]
  3. Ikehara M., Fukui T. Some physical properties of poly 7-deazaadenylic acid (poly Tubercidin phosphoric acid). J Mol Biol. 1968 Dec;38(3):437–441. doi: 10.1016/0022-2836(68)90399-9. [DOI] [PubMed] [Google Scholar]
  4. Ikehara M., Fukui T., Uesugi S. Polynucleotides. XXI. Synthesis and properties of poly 1-deazaadenylic acid and poly 3-deazaadenylic acid. J Biochem. 1974 Jul;76(1):107–115. doi: 10.1093/oxfordjournals.jbchem.a130534. [DOI] [PubMed] [Google Scholar]
  5. Ikehara M., Uesugi S. Polynucleotides. XVI. Oligomers of 8,2'-anhydro-8-mercapto-9-( -D-arabinofuranosyl)adennine 5'-monophosphate. J Am Chem Soc. 1972 Dec 27;94(26):9189–9193. doi: 10.1021/ja00781a033. [DOI] [PubMed] [Google Scholar]
  6. Ikehara M., Uesugi S., Yano J. Polynucleotides. XXIV. Synthesis and properties of a dinucleoside monophosphate derived from 8,2'-O-cycloadenosine. J Am Chem Soc. 1974 Jul 24;96(15):4966–4972. doi: 10.1021/ja00822a040. [DOI] [PubMed] [Google Scholar]
  7. Irie M. Inhibition of ribonuclease from Aspergillus saitoi by nucleosides. J Biochem. 1969 Jun;65(6):907–913. doi: 10.1093/oxfordjournals.jbchem.a129095. [DOI] [PubMed] [Google Scholar]
  8. Kondo N. S., Holmes H. M., Stempel L. M., Ts'o O. P. Influence of the phosphodiester linkage (3'-5', 2'-5', and 5'-5') on the conformation of dinucleoside monophosphate. Biochemistry. 1970 Sep 1;9(18):3479–3498. doi: 10.1021/bi00820a002. [DOI] [PubMed] [Google Scholar]
  9. Mizuno Y., Endo T., Ikeda K. Nucleotides. V. Syntheses of 2'-O-and 3'-O-(3-methyl-2-picolyl 1-oxide) ribonucleosides and diribonucleoside monophosphates by application of 3-methyl-2-picolyl 1-oxide protection. J Org Chem. 1975 May 16;40(10):1385–1390. doi: 10.1021/jo00898a003. [DOI] [PubMed] [Google Scholar]
  10. Mizuno Y., Kitano S., Nomura A. Nucleotides. III. Syntheses of deazaadenosine 3',5'-cyclic phosphates and related nucleotides of biological interest. Chem Pharm Bull (Tokyo) 1975 Aug;23(8):1664–1670. doi: 10.1248/cpb.23.1664. [DOI] [PubMed] [Google Scholar]
  11. Otsuka E., Nakamura S., Yoneda M., Ikehara M. Polynucleotides. 23. A synthesis of ribodinucleoside monophosphates using nucleoside 5'-phosphates. Nucleic Acids Res. 1974 Feb;1(2):323–329. doi: 10.1093/nar/1.2.323. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Philips K. D., Horwitz J. P. Nucleosides. XVII. Benzylation-debenzylation studies on nucleosides. J Org Chem. 1975 Jun 13;40(12):1856–1858. doi: 10.1021/jo00900a047. [DOI] [PubMed] [Google Scholar]
  13. Rousseau R. J., Townsend L. B., Robins R. K. The synthesis of 4-amino-beta-d-ribofuranosylimidazo[4,5-c]pyridine (3-deazaadenosine) and related nucleotides. Biochemistry. 1966 Feb;5(2):756–760. doi: 10.1021/bi00866a050. [DOI] [PubMed] [Google Scholar]
  14. Tazawa I., Tazawa S., Stempel L. M., Ts'o P. O. L'adenylyl-(3'-5')-L-adenosine and L-adenylyl-(2'-5')-L-adenosine. Biochemistry. 1970 Sep 1;9(18):3499–3514. doi: 10.1021/bi00820a003. [DOI] [PubMed] [Google Scholar]
  15. Uesugi S., Yasumoto M., Ikehara M., Fang K. N., Ts'o P. O. Synthesis and properties of the dinucleoside monophosphate of adenine 8-thiocyclonucleoside. J Am Chem Soc. 1972 Jul 26;94(15):5480–5486. doi: 10.1021/ja00770a053. [DOI] [PubMed] [Google Scholar]
  16. Van Holde K. E., Brahms J., Michelson A. M. Base interactions of nucleotide polymers in aqueous solution. J Mol Biol. 1965 Jul;12(3):726–739. doi: 10.1016/s0022-2836(65)80323-0. [DOI] [PubMed] [Google Scholar]

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