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Synthesis of a polyphosphorylated GPI-anchor core structure
Linköping University, The Institute of Technology. Linköping University, Department of Physics, Chemistry and Biology, Organic Chemistry .
2002 (English)In: Canadian journal of chemistry (Print), ISSN 0008-4042, Vol. 80, no 8, 1105-1111 p.Article in journal (Refereed) Published
Abstract [en]

Using a linear assembly approach a highly differentially protected derivative of the common GPI-anchor core structure (alpha-D-Man-(1-->6)-alpha-D-Man-(1-->2)-alpha-D-Man-(1-->4)-alpha-D-GlcNH(2)-(1-->6)-D-myo-inositol) has been synthesized. All mannose donors were prepared from a common thioglycoside precursor (1), and coupled to GlcN(3)-myo-inositol acceptor 5 in a linear five-step glycosylation-deprotection sequence in 49% overall yield, to give the key intermediate 10, with orthogonal temporary protecting groups at the 6", 2", 6', and 2 positions of the trimannoside motif and at the 1 and 2 positions of the inositol part. Consecutive removal of the temporary protecting groups in the trimannoside moiety followed by phosphorylation, gave a tetraphosphosphate derivative in 60% overall yield. Removal of a camphor acetal afforded a 1,2-inositol diol, which was converted to a 1,2-cyclic phosphate using commercial methyl dichlorophosphate (-->17, 95%). One-step deprotection using sodium in liquid ammonia afforded the target polyphosphorylated core structure 18 (60%), which will be tested for metabolic insulin action.

Place, publisher, year, edition, pages
2002. Vol. 80, no 8, 1105-1111 p.
Keyword [en]
glycophosphatidylinositols, linear synthesis, glycosylations, mositolphosphoglycans, IPG
National Category
Engineering and Technology
URN: urn:nbn:se:liu:diva-47849DOI: 10.1139/V02-160OAI: diva2:268745
Available from: 2009-10-11 Created: 2009-10-11 Last updated: 2011-01-13

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Konradsson, Peter
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