Carbasugars - Highly functionalized, Optically Active Carbocycles

  • Lundt, Inge (Project Manager)
  • Johansen, Steen Karsk (Project Participant)
  • Horneman, Anne Marie (Project Participant)
  • Wagner, Sussi Holstein (Project Participant)

    Project Details

    Description

    Glycosidases and glycosyltransferases are instrumental in the processing of various glycosylated proteins, which are ubiquitous in nearly all forms of life and play an important role in molecular recognition, adhesion and transport. The profound impact of these enzymes on life processes has made them desirable targets for inhibition. Glycoprocessing inhibitors have been used to treat diabetes, and have a potential as antiviral and antitumor agents.
    Important groups of inhibitors are azasugars and carbasugars, compounds which have structure similar to sugars, but in which the ring oxygen has been replaced by a nitrogen or a methylene group, respectively. These compounds mimic the sugar in question by occupying the catalytically active site in the enzyme, thus preventing the hydrolysis/glycosylation.
    Recently, we have developed a highly regio- and stereoselective procedure for synthesising carbasugars from the functionalized aldonolactones. Projects for stereoselective manipulation of the stereocenters as well as the stubstitution pattern are planned in order to approach carbasugars and other highly functionalize carbocyclic compounds. Among this type of compounds very active glycosidase inhibitors are known (Mannostatin, conduritols, as examples).
    StatusActive
    Effective start/end date01/02/1993 → …