154372-20-0Relevant academic research and scientific papers
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
First total synthesis of a GPI-anchored peptide
Xue, Jie,Shao, Ning,Guo, Zhongwu
, p. 4020 - 4029 (2007/10/03)
A GPI-anchored dipeptide of sperm CD52 antigen was prepared through a convergent synthesis. First, the dipeptide with its C-terminus free and the GPI with its nonreducing end phosphoeth-anolamine bearing a free amino group were synthesized separately. Then, the two building blocks were coupled with use of EDC/HOBt as the condensation reagent. Finally, the GPI-anchored peptide was deprotected to give the target molecule 1.
Convergent synthesis of an inner core GPI of sperm CD52
Xue, Jie,Guo, Zhongwu
, p. 2015 - 2018 (2007/10/03)
An inner core of the GPI anchor of sperm CD52 antigens was synthesized by a highly convergent process using specially modified inositol, glucosamine and phospholipid as key building blocks. This paper also presents a new and efficient procedure to prepare
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
