• Login
    View Item 
    •   Oxy Scholar Home
    • Chemistry
    • Chemistry URC Student Scholarship
    • View Item
    •   Oxy Scholar Home
    • Chemistry
    • Chemistry URC Student Scholarship
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    An Enantioselective Synthesis of DAB-1

    Thumbnail
    Author
    Jordan, Robert
    Issue
    urc_student; urc_student
    Date
    2009-01-01 0:00
    Metadata
    Show full item record
    URI
    https://scholar.oxy.edu/handle/20.500.12711/557
    Abstract
    A synthetic route for enantio-pure α-glucosidase inhibitor DAB-1 is investigated. In the mammalian digestive tract, the enzyme α-glucosidase catalyzes a key step in the degradation of glycogen. By inhibiting this enzyme, the rate at which glucose is produced in the cell can be specifically controlled. The control of blood glucose levels has far reaching use in the treatment of diabetes and also hypoglycemia. The enatiomeric pair of 1,4-dideoxy-1,4-imino-arabinitol (DAB-1 and LAB-1) has shown to be prominent inhibitors of α-glucosidases. Derivatives of DAB-1 have also been used to disrupt the construction of HIV virus glycoproteins within host cells. It is for these reasons that efficient, economical syntheses of DAB-1 and LAB-1 have wide importance to the scientific community. Using a robust enzyme named oxynitrilase, derived from almonds, we establish chirality in an achiral molecular backbone and maintain enantiomeric integrity throughout subsequent synthetic steps in enatiomeric excesses of >95%. By utilizing Palladium(0) catalysis, we can transpose the stereocenter while maintaining enantiomeric integrity throughout the synthetic route. Further manipulation of the chiral backbone affords the title compound in an efficient and economical manner.
    Collections
    • Chemistry URC Student Scholarship

    Browse

    All of Oxy ScholarCommunities & CollectionsBy Issue DateAuthorsTitlesSubjectsJournal TitleJournal IssueThis CollectionBy Issue DateAuthorsTitlesSubjectsJournal TitleJournal Issue

    My Account

    LoginRegister

    DSpace software copyright © 2002-2021  DuraSpace
    Contact Us | Send Feedback
    DSpace Express is a service operated by 
    Atmire NV