Synthesis of the essential core of the human glycosylphosphatidylinositol (GPI) anchor.
The biological role of GPI anchors is of paramount importance; however, we are still far from fully understanding the structure-function relationship of these molecules. One major limiting factor has been the tiny quantities available from natural sources; obtaining homogeneous and well-defined GPI structures by synthesis, is both a challenge and an attractive goal. We report here the convergent synthesis of the essential core of the human GPI anchor 1, exploiting a common precursor to obtain the trisaccharidic donor 2 and a novel protecting groups sequence. The final product, prepared for the first time, is biologically active.
Dipartimento di Chimica, Universita' di Firenze, Italy.
Barbara
B
Richichi
Lucio
L
Luzzatto
Rosario
R
Notaro
Giancarlo
G
la Marca
Cristina
C
Nativi
D017261:Glycosylphosphatidylinositols / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D014312:Trisaccharides / Q000737:chemistry
C559297:(6-O-aminoethylphosphonato-mannopyranosyl)-(1-2)-mannopyranosyl-(1-6)-mannopyranosyl-(1-4)-(2-amino-2-deoxyglucopyranosyl)-(1-6)-1-O-(1,2-di-O-octadecanoyl-sn-glyceryl-phosphonato)-myo-inositol; D017261:Glycosylphosphatidylinositols; D009844:Oligosaccharides; D012997:Solvents; D014312:Trisaccharides; D010165:Palladium