Chemical synthesis of parasitic glycoconjugates and phosphoglycans

Nawaf Al-Maharik, Jennifer A. Tee, Andrei V. Nikolaev

    Research output: Chapter in Book/Report/Conference proceedingChapter

    Abstract

    The glycosylphosphatidylinositols (GPIs) are a class of natural glycosylphospholipids that anchor proteins, glycoproteins, and lipophosphoglycans (LPGs) to the membrane of eukaryotic cells. This chapter reviews the progress and recent achievements in the chemical synthesis of the glycoconjugate structures like glycosylphosphatidylinositol anchors and phosphoglycans of the protozoan parasites Trypanosoma brucei, Trypanosoma cruzi, Toxoplasma gondii, Plasmodium falciparum, and Leishmania. Synthetic strategies toward GPI anchors and GPI-related glycoconjugates have matured since the first synthesis published in the early 1990s. Several attractive synthetic routes used for the preparation of the parasitic structures discussed in this chapter. In addition, synthesis of a GPI anchor found in the yeast Saccharomyces cerevisiae and a few structures from the higher eukaryotes have been discussed. A common feature in most of the strategies used (with the exception of CD52 GPIs) is the initial construction of the GPI glycan core having the appropriate orthogonal protecting groups, followed by subsequent introduction of the phosphate moieties. Almost all strategies use benzyl ethers as permanent O-protecting groups.
    Original languageEnglish
    Title of host publicationMicrobial glycobiology
    Subtitle of host publicationstructures, relevance and applications
    EditorsAnthony P. Moran, Otto Holst, Patrick J. Brennan, Mark von Itzstein
    Place of PublicationLondon
    PublisherAcademic Press
    Pages477-548
    Number of pages72
    ISBN (Print)9780123745460
    DOIs
    Publication statusPublished - 2010

    Fingerprint

    Glycosylphosphatidylinositols
    Glycoconjugates
    Yeast
    Ethers
    Anchors
    Polysaccharides
    Glycoproteins
    Phosphates
    Membranes

    Cite this

    Al-Maharik, N., Tee, J. A., & Nikolaev, A. V. (2010). Chemical synthesis of parasitic glycoconjugates and phosphoglycans. In A. P. Moran, O. Holst, P. J. Brennan, & M. von Itzstein (Eds.), Microbial glycobiology: structures, relevance and applications (pp. 477-548). London: Academic Press. https://doi.org/10.1016/B978-0-12-374546-0.00026-2
    Al-Maharik, Nawaf ; Tee, Jennifer A. ; Nikolaev, Andrei V. / Chemical synthesis of parasitic glycoconjugates and phosphoglycans. Microbial glycobiology: structures, relevance and applications. editor / Anthony P. Moran ; Otto Holst ; Patrick J. Brennan ; Mark von Itzstein. London : Academic Press, 2010. pp. 477-548
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    Al-Maharik, N, Tee, JA & Nikolaev, AV 2010, Chemical synthesis of parasitic glycoconjugates and phosphoglycans. in AP Moran, O Holst, PJ Brennan & M von Itzstein (eds), Microbial glycobiology: structures, relevance and applications. Academic Press, London, pp. 477-548. https://doi.org/10.1016/B978-0-12-374546-0.00026-2

    Chemical synthesis of parasitic glycoconjugates and phosphoglycans. / Al-Maharik, Nawaf; Tee, Jennifer A.; Nikolaev, Andrei V.

    Microbial glycobiology: structures, relevance and applications. ed. / Anthony P. Moran; Otto Holst; Patrick J. Brennan; Mark von Itzstein. London : Academic Press, 2010. p. 477-548.

    Research output: Chapter in Book/Report/Conference proceedingChapter

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    Al-Maharik N, Tee JA, Nikolaev AV. Chemical synthesis of parasitic glycoconjugates and phosphoglycans. In Moran AP, Holst O, Brennan PJ, von Itzstein M, editors, Microbial glycobiology: structures, relevance and applications. London: Academic Press. 2010. p. 477-548 https://doi.org/10.1016/B978-0-12-374546-0.00026-2