Synthesis of phosphatidylinositol mannosides (PIMs).
Two strategies towards the synthesis of phosphatidylinositol mannosides (PIMs) were elaborated which permit selective access to the O-1-, O-2-, and the O-6 position of the myo-inositol residue. Starting materials are 1,2:5,6- and 1,2:4,5-di-O-cyclohexylidene-DL-myo-inositol, respectively. In the latter case, the required assignment to the D- or L-series is based on the transformation of one enantiomer into known (-)-liriodentritol. The efficiency and potential versatility of the two approaches is exemplified in the synthesis of PIMs (D)-1a and its pseudoenantiomer (L)-1b, both having myristoyl residues as part of the phosphatidyl moiety.
Stadelmaier
Andreas
A
Fachbereich Chemie, Universität Konstanz, Fach M 725, D-78457 Konstanz, Germany.
Schmidt
Richard R
RR
D002240:Carbohydrate Sequence; D007294:Inositol / Q000737:chemistry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D010716:Phosphatidylinositols / Q000138:chemical synthesis* / Q000737:chemistry
D010716:Phosphatidylinositols; C034154:phosphatidylinositol mannoside; D007294:Inositol