Skip NavigationSkip to Content
Return Return to Search Results

Using conformationally locked nucleosides to calibrate the anomeric effect: implications for glycosyl bond stability

  1. Author:
    Moon, H. R.
    Siddiqui, M. A.
    Sun, G.
    Filippov, I. V.
    Landsman, N. A.
    Lee, Y. C.
    Adams, K. M.
    Barchi, J. J.
    Deschamps, J. R.
    Nicklaus, M. C.
    Kelley, J. A.
    Marquez, V. E.

  2. Author Address

    [Moon, Hyung Ryong; Siddiqui, Maqbool A.; Sun, Guangyu; Landsman, Nicholas A.; Lee, Yi-Chien; Adams, Kristie M.; Barchi, Joseph J., Jr.; Nicklaus, Marc C.; Kelley, James A.; Marquez, Victor E.] NCI, Biol Chem Lab, Ctr Canc Res, NIH, Frederick, MD 21701 USA. [Filippov, Igor V.] SAIC Frederick Inc, Frederick, MD 21702 USA. [Deschamps, Jeffrey R.] USN, Res Lab, Washington, DC 20375 USA.;Marquez, VE, NCI, Biol Chem Lab, Ctr Canc Res, NIH, Frederick, MD 21701 USA.;marquezv@mail.nih.gov
    1. Year: 2010
    2. Date: Aug
  2. Journal: Tetrahedron
    1. 66
    2. 34
    3. Pages: 6707-6717
  4. Type of Article: Article
  5. ISSN: 0040-4020
  1. Abstract:

    Steric and electronic parameters, such as the anomeric effect (AE) and gauche effect play significant roles in steering the North <-> South equilibrium of nucleosides in solution. Two isomeric oxa-bicyclo[3.1.0]hexane nucleosides that are conformationally locked in either the North or the South conformation of the pseudorotational cycle were designed to study the consequences of having the AE operational or not, independent of other parameters. The rigidity of the system allowed the orientation of the orbitals involved to be set in 'fixed' relationships, either antiperiplanar where the AE is permanently 'on', or gauche where the AE is impaired. The consequences of these two alternatives were subjected to high-level calculations and measured experimentally by X-ray crystallography, hydrolytic stability of the glycosyl bond, and pK(a) values. Published by Elsevier Ltd.

    See More

  1. Keywords:

External Sources

  1. View Full Text
  2. DOI: 10.1016/j.tet.2010.06.044
  3. View record in Web of Science®
  4. WOS: 000280953500002

Library Notes

  1. Fiscal Year: FY2009-2010
NCI at Frederick

You are leaving a government website.

This external link provides additional information that is consistent with the intended purpose of this site. The government cannot attest to the accuracy of a non-federal site.

Linking to a non-federal site does not constitute an endorsement by this institution or any of its employees of the sponsors or the information and products presented on the site. You will be subject to the destination site's privacy policy when you follow the link.

ContinueCancel