154459-82-2Relevant articles and documents
Synthesis of non-hydrolysable mimics of glycosylphosphatidylinositol (GPI) anchors
Yadav, Mahipal,Raghupathy, Riya,Saikam, Varma,Dara, Saidulu,Singh, Parvinder Pal,Sawant, Sanghapal D.,Mayor, Satyajit,Vishwakarma, Ram A.
supporting information, p. 1163 - 1172 (2014/02/14)
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. The Royal Society of Chemistry.
Stereoselective α-glycosylation of C(6)-hydroxyl myo-inositols via nickel catalysis - Application to the synthesis of GPI anchor pseudo-oligosaccharides
McConnell, Matthew S.,Mensah, Enoch A.,Nguyen, Hien M.
supporting information, p. 146 - 152 (2013/11/06)
Glycosylphosphatidyl inositol (GPI) anchors play a key role in many eukaryotic biological pathways. Stereoselective synthesis of GPI anchor analogues have proven to be critical for probing the biosynthesis, structure, and biological properties of these co
Synthesis of new fluorescently labeled glycosylphosphatidylinositol (GPI) anchors
Saikam, Varma,Raghupathy, Riya,Yadav, Mahipal,Gannedi, Veeranjaneyulu,Singh, Parvinder Pal,Qazi, Naveed A.,Sawant, Sanghapal D.,Vishwakarma, Ram A.
supporting information; experimental part, p. 4277 - 4279 (2011/09/12)
The borondipyrromethene (BODIPY) labeled new glycosylphosphatidylinositol (GPI) molecules were synthesized as cellular probes to study the chemical basis of microdomain organization of GPI-anchored proteins and cholesterol in plasma membrane. The synthesi
Efficient syntheses of chiral myo-inositol derivatives-key intermediates in glycosylphosphatidylinositol (GPI) syntheses
Yu, Fei,Guo, Zhongwu
scheme or table, p. 3852 - 3855 (2010/03/02)
A facile and effective method was developed for large-scale syntheses of myo-inositol derivatives with the 1,2,6-O-positions differentiated from each other and from other positions as well. The syntheses started from methyl α-d-glucopyranoside, and the ke
Further probing of the substrate specificities and inhibition of enzymes involved at an early stage of glycosylphosphatidylinositol (GPI) biosynthesis
Crossman Jr., Arthur,Paterson, Michael J.,Ferguson, Michael A.J.,Smith, Terry K.,Brimacombe, John S.
, p. 2049 - 2059 (2007/10/03)
1-D-6-O-(2-Amino-2-deoxy-α-D-glucopyranosyl)-1-O-hexadecyl-myo-inositol (14), 1-D-6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-myo-inositol 1-(octadecyl phosphate) (18), 1-D-6-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-myo-inositol 1-(1,2-di-O-hexadecanoyl-sn-gly
Synthesis of the fully phosphorylated GPI anchor pseudohexasaccharide of Toxoplasma gondii
Pekari,Tailler,Weingart,Schmidt
, p. 7432 - 7442 (2007/10/03)
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.
Parasite Glucoconjugates. Part 1. The Synthesis of Some Early and Related Intermediates in the Biosynthetic Pathway of Glycosyl-phosphatidylinositol Membrane Anchors
Cottaz, Sylvain,Brimacombe, John S.,Ferguson, Michael A. J.
, p. 2945 - 2952 (2007/10/02)
The enantio-pure 1D- and 1L-myo-inositol derivative 3D and 3L have been used to prepare sodium 1D-6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-myo-inositol sn-2,3-dipalmitoyloxypropyl phosphate 21 and a related 1,6-disubstituted 1L-myo-inositol 28, respective
