Parasite glycoconjugates. Part 1: the synthesis of some early and related intermediates in the biosynthetic pathway of glycosyl-phosphatidylinositol membrane anchors

Sylvain Cottaz, John S. Brimacombe, Michael A. J. Ferguson

    Research output: Contribution to journalArticle

    10 Citations (Scopus)

    Abstract

    The enantio-pure 1D- and 1L-myo-inositol derivatives 3D and 3L have been used to prepare sodium 1D-6-O-(2-amino-2-deoxy-a-D-glucopyranosyl)-myo- inositol sn-2,3-dipalmitoyloxypropyl phosphate 21 and a related 1,6-disubstituted 1L-myo-inositol 28, respectively. The hydrogenphosphonate approach was effective in coupling together the phosphonolipid moiety 16 and the protected 6-O-(2-azido-2-deoxy-a-D-glucopyranosyl)-myo-inositols 15 and 24, respectively.
    Original languageEnglish
    Pages (from-to)2945-2951
    Number of pages7
    JournalJournal of the Chemical Society - Perkin Transactions 1
    Issue number23
    DOIs
    Publication statusPublished - 1 Jan 1993

    Fingerprint

    Glycosylphosphatidylinositols
    Glycoconjugates
    Inositol
    Anchors
    Membranes
    Sodium
    Phosphates
    Derivatives
    Biosynthetic Pathways
    Parasites

    Cite this

    @article{f4177605b13d4a03b6940b7408c7aa20,
    title = "Parasite glycoconjugates. Part 1: the synthesis of some early and related intermediates in the biosynthetic pathway of glycosyl-phosphatidylinositol membrane anchors",
    abstract = "The enantio-pure 1D- and 1L-myo-inositol derivatives 3D and 3L have been used to prepare sodium 1D-6-O-(2-amino-2-deoxy-a-D-glucopyranosyl)-myo- inositol sn-2,3-dipalmitoyloxypropyl phosphate 21 and a related 1,6-disubstituted 1L-myo-inositol 28, respectively. The hydrogenphosphonate approach was effective in coupling together the phosphonolipid moiety 16 and the protected 6-O-(2-azido-2-deoxy-a-D-glucopyranosyl)-myo-inositols 15 and 24, respectively.",
    author = "Sylvain Cottaz and Brimacombe, {John S.} and Ferguson, {Michael A. J.}",
    note = "Copyright 2007 Elsevier B.V., All rights reserved.",
    year = "1993",
    month = "1",
    day = "1",
    doi = "10.1039/P19930002945",
    language = "English",
    pages = "2945--2951",
    journal = "Journal of the Chemical Society - Perkin Transactions 1",
    issn = "0300-922X",
    publisher = "Royal Society of Chemistry",
    number = "23",

    }

    TY - JOUR

    T1 - Parasite glycoconjugates. Part 1

    T2 - the synthesis of some early and related intermediates in the biosynthetic pathway of glycosyl-phosphatidylinositol membrane anchors

    AU - Cottaz, Sylvain

    AU - Brimacombe, John S.

    AU - Ferguson, Michael A. J.

    N1 - Copyright 2007 Elsevier B.V., All rights reserved.

    PY - 1993/1/1

    Y1 - 1993/1/1

    N2 - The enantio-pure 1D- and 1L-myo-inositol derivatives 3D and 3L have been used to prepare sodium 1D-6-O-(2-amino-2-deoxy-a-D-glucopyranosyl)-myo- inositol sn-2,3-dipalmitoyloxypropyl phosphate 21 and a related 1,6-disubstituted 1L-myo-inositol 28, respectively. The hydrogenphosphonate approach was effective in coupling together the phosphonolipid moiety 16 and the protected 6-O-(2-azido-2-deoxy-a-D-glucopyranosyl)-myo-inositols 15 and 24, respectively.

    AB - The enantio-pure 1D- and 1L-myo-inositol derivatives 3D and 3L have been used to prepare sodium 1D-6-O-(2-amino-2-deoxy-a-D-glucopyranosyl)-myo- inositol sn-2,3-dipalmitoyloxypropyl phosphate 21 and a related 1,6-disubstituted 1L-myo-inositol 28, respectively. The hydrogenphosphonate approach was effective in coupling together the phosphonolipid moiety 16 and the protected 6-O-(2-azido-2-deoxy-a-D-glucopyranosyl)-myo-inositols 15 and 24, respectively.

    UR - http://www.scopus.com/inward/record.url?scp=37049088320&partnerID=8YFLogxK

    U2 - 10.1039/P19930002945

    DO - 10.1039/P19930002945

    M3 - Article

    AN - SCOPUS:37049088320

    SP - 2945

    EP - 2951

    JO - Journal of the Chemical Society - Perkin Transactions 1

    JF - Journal of the Chemical Society - Perkin Transactions 1

    SN - 0300-922X

    IS - 23

    ER -