140391-29-3Relevant academic research and scientific papers
Synthesis of D-erythro-ceramide-1-phosphoinositol and its aminoglucosylated derivative - Intermediates in GPI-anchor biosynthesis
Kratzer, Bernd,Mayer, Thomas G.,Schmidt, Richard R.
, p. 291 - 298 (2007/10/03)
The readily available 2,3:4,5-di-O-cyclohexylidene-D-myo-inositol derivative 3 was converted into the 1-O-unprotected D-myo-inositol derivative 6. Reaction with the phosphite derivative 7 of 3-O-tert-butyldimethylsilyl-protected ceramide furnished the target molecule D-erythro-ceramide-1-phosphoinositol (1). Reaction of O-(3,4,6-tri-O-acetyl-2-azido-β-D-glucopyranosyl)trichloroacetimidate (20) with 3 gave exclusively α(1→6)-connected glycoside 21 which was converted into the 1α-O-unprotected derivative 24. Reaction with the D-erythro-azidophytosphingosine-derived ceramide-1-phosphite derivative 17 led, after oxidation and removal of the cyanoethyl group, to protected 2-azido-D-glucopyranosyl-α(1→6)-D-myo-inositol-1-phospho-ceramide (25) which could bo fully deprotected in two steps to afford the target molecule, the ceramide derivative of 2-amino-2-deoxy-D-glucopyranosyl-α(1→6)-D-myo-inositol-1-phosphate (2).
GPI membrane anchors: Synthesis and functional evaluation of aminoglucosyl phosphatidylinositol core analogs
Ye, Jianhua,Doerrler, William T.,Lehrman, Mark A.,Falck
, p. 1715 - 1718 (2007/10/03)
Analogs of GPI membrane anchor precursors were prepared from chiral inositol 1 and evaluated as substrates in rodent and trypanosomal cell-free incubates. Di-octanoyl GlcNα-PI 5b was an efficient mannose acceptor whereas di-palmitoyl GlcNα-PI 5a was unexpectedly refractory. Di-octanoyl β-anomer 8 was mannosylated only under conditions that permitted acylation of the inositol residue.
