The chemical synthesis of glycosylphosphatidylinositol anchors from Trypanosoma cruzi Trypomastigote mucins: exploration of ester and acetal type permanent protecting groups

Dmitry V. Yashunsky, Vladimir S. Borodkin, Philip G. McGivern, Michael A. J. Ferguson, Andrei V. Nikolaev

    Research output: Chapter in Book/Report/Conference proceedingConference contribution

    Abstract

    The protozoan parasite Trypanosoma cruzi is a causative agent of Chagas' disease, which affects millions of people in South and Central America. Throughout the life cycle, T cruzi produce both common and stage-specific glycosylphosphatidylinositol(GPI)-anchored cell-surface macromolecules. The purified GPI fraction of T cruzi trypomastigote mucins (tGPI) revealed extraordinary pro-inflammatory activity (comparable to those of bacterial lipopolysaccharide), which was allegedly associated with the presence of unsaturated fatty acids in the lipid moiety (structures 1 and 2). Two distinct novel synthetic strategies, both implicating the use of non-benzyl type protecting groups, were designed and applied for the chemical preparation of the tGPIs 1 and 2.

    Original languageEnglish
    Title of host publicationFrontiers in modern carbohydrate chemistry
    EditorsA. V. Demchenko
    Place of PublicationWashington
    PublisherAmerican Chemical Society
    Pages285-306
    Number of pages22
    ISBN (Electronic)9780841220782
    ISBN (Print)9780841239708
    DOIs
    Publication statusPublished - 2007
    EventThe 229th ACS National Meeting 2005: Symposium on Frontiers in Modern Carbohydrate Chemistry - San Diego, United States
    Duration: 13 Mar 200517 Mar 2005
    http://oasys2.confex.com/acs/229nm/techprogram/

    Publication series

    NameACS Symposium series
    Volume960

    Conference

    ConferenceThe 229th ACS National Meeting 2005: Symposium on Frontiers in Modern Carbohydrate Chemistry
    CountryUnited States
    CitySan Diego
    Period13/03/0517/03/05
    Internet address

    Keywords

    • RAT-BRAIN THY-1
    • GPI-ANCHOR
    • MEMBRANE ANCHOR
    • BIOSYNTHESIS
    • GLYCOPROTEIN
    • DERIVATIVES
    • FRAGMENT
    • PARASITE
    • ANALOGS
    • BRUCEI

    Cite this

    Yashunsky, D. V., Borodkin, V. S., McGivern, P. G., Ferguson, M. A. J., & Nikolaev, A. V. (2007). The chemical synthesis of glycosylphosphatidylinositol anchors from Trypanosoma cruzi Trypomastigote mucins: exploration of ester and acetal type permanent protecting groups. In A. V. Demchenko (Ed.), Frontiers in modern carbohydrate chemistry (pp. 285-306). (ACS Symposium series; Vol. 960). American Chemical Society. https://doi.org/10.1021/bk-2007-0960.ch016