Chemistry of Natural Compounds

, Volume 18, Issue 6, pp 703–708 | Cite as

Oligonucleotides and nucleotidopeptides. XLII. Efficacy of the intramolecular influence of the carboxy groups of amino acids in nucleotidyl-(P → N)-amino acids (peptides) as a function of their positions

  • B. A. Yuodka
  • L. E. Lioranchaite
  • V. R. Baltenas


It has been established that remote carboxy groups in nucleotidyl-(5′ → N)-β-alanine and -alanylalanine do not affect the mechanism of the cleavage of the phosphoramide center. The situation is different in the case of nucleotidyl-(5′ → Nɛ)-lysine. It has been shown that in the 3′-phenylalanine derivative of dTMP, the influence of the α-carboxy group of the amino acid is only half as great as in the 5′-analog. The α-carboxy groups of the amino acids in oligonucleotidyl-(Pin → N)-amino acids also weaken the mechanism of the cleavage of the phosphoramide centers.


Carboxy Group Hydrolytic Stability Phosphoramide Amino Acid Ester Carbonyldiimidazole 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    B. A. Yuodka, Bioorg. Khim.,6, No. 10, 1445 (1981).Google Scholar
  2. 2.
    B. A. Yuodka, ″Covalent interactions of proteins and nucleic acids. Synthetic and natural nucleotidopeptides,″ Author's abstract of Doctoral dissertation, Vilnius (1981).Google Scholar
  3. 3.
    V. A. Yuodka, S. I. Sasnauskene, S. A. Kazlauskaite, V. A. Kirvyalene, and Z. A. Shabarova, Bioorg. Khim.,7, No. 2, 240 (1981).Google Scholar
  4. 4.
    J. G. Moffatt and H. G. Khorana, J. Am. Chem. Soc.,83, No. 3, 649 (1961).CrossRefGoogle Scholar
  5. 5.
    N. I. Sokolova, G. I. Gurova, L. G. Gatinskaya, Z. A. Shabarova, and M. A. Prokof'ev, Mol. Biol.,3, No. 6, 837 (1969).Google Scholar
  6. 6.
    V. V. Shumyantzeva, N. I. Sokolova, and Z. A. Shabarova, Nucleic Acids Res.,3, No. 4, 903 (1976).CrossRefGoogle Scholar
  7. 7.
    J. P. Greenstein and M. A. Winitz, Chemistry of the Amino Acids, Wiley, New York (1961).Google Scholar
  8. 8.
    G. M. Tener, J. Am. Chem. Soc.,83, No. 1, 159 (1961).CrossRefGoogle Scholar
  9. 9.
    M. Smith, D. H. Rammler, I. H. Goldberg, and H. G. Khorana, J. Am. Chem. Soc.,84, No. 3, 430 (1962).CrossRefGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1983

Authors and Affiliations

  • B. A. Yuodka
  • L. E. Lioranchaite
  • V. R. Baltenas

There are no affiliations available

Personalised recommendations