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Issue 7, 2014
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Synthesis of non-hydrolysable mimics of glycosylphosphatidylinositol (GPI) anchors

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Abstract

Synthesis of first generation non-hydrolysable C-phosphonate GPI analogs, viz., 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol-1-O-(sn-3,4-bis(palmitoyloxy)butyl-1-phosphonate) 23a and 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol-1-O-(sn-2,3-bis(palmitoyloxy)propyl-1-phosphonate) 23b, is reported. The target compounds were synthesized by the coupling of α-pseudodisaccharide 21 with phosphonic acids 18a and 18b respectively in quantitative yield followed by de-protection. These synthetic C-phosphonate GPI-probes were resistant to phosphatidylinositol specific phospholipase C (PI-PLC) and also showed moderate inhibition of the enzyme activity.

Graphical abstract: Synthesis of non-hydrolysable mimics of glycosylphosphatidylinositol (GPI) anchors

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Publication details

The article was received on 24 Oct 2013, accepted on 03 Dec 2013 and first published on 03 Dec 2013


Article type: Paper
DOI: 10.1039/C3OB42116C
Org. Biomol. Chem., 2014,12, 1163-1172

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    Synthesis of non-hydrolysable mimics of glycosylphosphatidylinositol (GPI) anchors

    M. Yadav, R. Raghupathy, V. Saikam, S. Dara, P. P. Singh, S. D. Sawant, S. Mayor and R. A. Vishwakarma, Org. Biomol. Chem., 2014, 12, 1163
    DOI: 10.1039/C3OB42116C

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