- Synthesis of biotin-labelled core glycans of GPI anchors and their application in the study of GPI interaction with pore-forming bacterial toxins
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A convergent strategy was developed for the first-time synthesis of biotin-labeled GPI core glycans. These GPI conjugates are useful for various biological studies showcased by their application in the scrutiny of pore-forming bacterial toxin-GPI interaction, revealing that the phosphate group at the GPI inositol 1-O-position had a significant impact on GPI-toxin binding.
- Gao, Jian,Zhou, Zhifang,Guo, Jiatong,Guo, Zhongwu
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- Total synthesis of the fully lipidated glycosylphosphatidylinositol (GPI) anchor of malarial parasite Plasmodium falciparum
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We report a new and convergent strategy for the total synthesis of fully lipidated glycosylphosphatidylinositol (GPI) anchor, the major pro-inflammatory factor of malarial parasite (Plasmodium falciparum). The key features of our approach include, the acc
- Ali, Asif,Vishwakarma, Ram A.
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scheme or table
p. 4357 - 4369
(2010/07/06)
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- A new approach to construct full-length glycosylphosphatidylinositols of parasitic protozoa and [4-deoxy-Man-III]-GPI analogues
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A new [2 + 2 + 2] approach to construct GPI molecules through the efficient synthesis of glucosamine-inositol and tetramannose intermediates led to a total synthesis of a GPI-anchor of Trypanosoma cruzi, and also afforded a key intermediate for the synthe
- Ali, Asif,Gowda, D. Channe,Vishwakarma, Ram A.
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p. 519 - 521
(2008/09/18)
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- Synthesis of the fully phosphorylated GPI anchor pseudohexasaccharide of Toxoplasma gondii
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Retrosynthesis of the fully phosphorylated glycosylphosphatidyl inositol (GPI) anchor pseudohexasaccharide 1a led to building blocks 2-6, of which 5 and 6 are known. The formation of pseudodisaccharide building block 2 is based on readily available building block 7, which gave, via derivative 11 and its glycosylation with known donor 12, the desired compound 2. Building block 3, with the required access to all hydroxy groups being permitted, was prepared from mannose in five steps. From a readily available precursor, building block 4 was obtained, which on reaction with 3 gave disaccharide 23. The synthesis of the decisive pseudohexasaccharide intermediate 32 was based on the reaction of 23 with 5, then with 6, and finally with 2. To obtain high stereoselectivity and good yields in the glycosylation reactions, anchimeric assistance was employed. To enable regioselective attachment of the two different phosphorus esters, the 6f-O-silyl group of 32 was first removed and the aminoethyl phosphate residue was attached. Then the MPM group was oxidatively removed, and the second phosphate residue was introduced. Unprotected 1a was then liberated in two steps: treatment with sodium methanolate removed the acetyl protecting groups, and finally, catalytic hydrogenation afforded the desired target molecule, which could be fully structurally assigned.
- Pekari,Tailler,Weingart,Schmidt
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p. 7432 - 7442
(2007/10/03)
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