Abstract
The hydroxyl group at C-5 in racemic 1,2-O-Cyclohexylidene-myo-inositol (rac-1) was regio- and enantioselectively acylated to give 5-O-acetyl- (2a)- or 5-O-butyryl-2,3-O-cyclohexylidene-myo-inositol (3a), respectively, by treatment of 1 with vinyl acetate or 2,2,2-trifluoroethyl butyrate in the presence of crude porcine pancreatic lipase in various organic solvents. Compound 2a was phosphorylated and deprotected to give myo-inositol 1,4,6-trisphosphate (8). Compound 2a was deacetylated and the resulting 2,3-O-cyclohexylidene-myo-inositol (1) was converted to myo-inositol 1,4,5,6-tetrakisphosphate (6).
| Original language | English (US) |
|---|---|
| Pages (from-to) | 533-537 |
| Number of pages | 5 |
| Journal | Liebigs Annales |
| Issue number | 4 |
| DOIs | |
| State | Published - Apr 1996 |
| Externally published | Yes |
Keywords
- Enzyme-catalyzed esterification
- Lipases
- Regio- and enantioselectivity
- myo-Inositol 1,4,5,6-tetrakisphosphate
- myo-Inositol 1,4,6-trisphosphate
ASJC Scopus subject areas
- General Chemistry