Advertisement

Chemistry of Natural Compounds

, Volume 4, Issue 2, pp 93–98 | Cite as

Influence of a remote oh group on the stability of the phosphoramide bond in an ester of uridylyl(5′→N)alanine

  • V. D. Smirnov
  • N. G. Shinskii
  • Z. A. Shabarova
  • M. A. Prokof'ev
Article

Summary

1. The ethyl and hydroxyethyl esters of uridylyl(5′→N) alanine have been synthesized and their comparative hydrolytic stabilities in the pH region from 0 to 8 have been studied.

2. It has been shown that the presence of a remote hydroxy group in the molecule of a uridylyl(5′→N)amino acid makes the phosphoramide link more labile in the region of weakly acid and neutral pH values.

3. At pH 3–5, the hydroxy ethyl ester of uridylyl(5′→N)alanine undergoes an intramolecular rearrangement with the cleavage of the phosphoramide linkage and the formation of a phosphoric diester linkage.

Keywords

Hydroxyl Oxygen Phosphoramide Azeotropic Distillation Caustic Potash Dihydropyran 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    O.E. Vorob'ev, Z.A. Shabarova, and M.A. Prokof'ev, DAN SSSR, 158, 143, 1964.Google Scholar
  2. 2.
    O.E. Vorob'ev, Z.A. Shabarova, and M.A. Prokof'ev, Vestnik MGU, Ser. khim., no. 6, 66.1964.Google Scholar
  3. 3.
    V.A. Bakanova, Z.A. Shabarova, and M.A. Prokof'ev, KhPS [Chemistry of Natural Compounds], 2, 35, 1966.CrossRefGoogle Scholar
  4. 4.
    O.E. Vorob'ev, Z.A. Shabarova, and M.A. Prokof'ev, ZhOKh, 34, 359, 1964.Google Scholar
  5. 5.
    O.E. Vorob'ev, Synthesis and Properties of Amino Acid Derivatives of Mono-and Dinucleotide Phosphates [in Russian], Moscow, 1965.Google Scholar
  6. 6.
    Z.A. Shabarova, H.A. Huges, and J. Baddily, Biochem J., 83, 216, 1962.CrossRefGoogle Scholar
  7. 7.
    M. Halmann, A. Lapidot, and D. Samuel, J. Chem. Soc., 1299, 1963.Google Scholar

Copyright information

© The Faraday Press, Inc. 1969

Authors and Affiliations

  • V. D. Smirnov
    • 1
  • N. G. Shinskii
    • 1
  • Z. A. Shabarova
    • 1
  • M. A. Prokof'ev
    • 1
  1. 1.Moscow State UniversityUSSR

Personalised recommendations