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What are the consequences of freezing the anomeric effect in nucleosides?

  1. Author:
    Marquez, V. E.
    Sun, G.
    Siddiqui, M. A.
    Lee, Y. C.
    Barchi, J. J., Jr.
    Filippov, I. V.
    Landsman, N. A.
    Kelley, J. A.

  2. Author Address

    Laboratory of Medicinal Chemistry, Center for Cancer Research, National Cancer Institute at Frederick, National Institutes of Health, Frederick, Maryland 21702, USA. marquezv@mail.nih.gov
    1. Year: 2008
    2. Epub Date: 9/9/2008
  2. Journal: Nucleic acids symposium series (2004)
    1. 52
    2. Pages: 543-4
  4. Type of Article: Article
  5. ISSN: 1746-8272 (Electronic);0261-3166 (Linking)
  1. Abstract:

    The consequences of freezing the orientation of the oxygen's lone pair orbitals--which determines whether the anomeric effect is operative or not--were studied theoretically and experimentally in two oxobicyclo-[3.1.0]hexane nucleosides (1 and 2). The results showed significant differences in the properties of these molecules, which correlated with the magnitude of the n2 --> sigma * delocalization.

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  2. DOI: 10.1093/nass/nrn275
  3. PMID: 18776494
  4. PMCID: PMC2700545
  5. NIHMSID: Nihms120286

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