A chemoenzymatic synthesis of D-myo-inositol 1,4,5-trisphosphate.
Enzyme-catalyzed esterification of racemic 2,3-O-cyclohexylidene-myo-inositol (DL-1) proceeded exclusively in 1,4-dioxane to give optically pure L-1-O-acetyl-2,3-O-cyclohexylidene-myo-inositol (L-2) and D-2,3-O-cyclohexylidene-myo-inositol (D-1). A new practical route has been developed for the synthesis of D-myo-inositol 1,4,5-trisphosphate starting from D-1 via selective acylation of the 6-hydroxyl group.
Ling
L
L
Department of Applied Chemistry, Faculty of Engineering, Ehime University, Matsuyama, Japan.
Ozaki
S
S
D007202:Indicators and Reagents; D007294:Inositol / Q000031:analogs & derivatives; D015544:Inositol 1,4,5-Trisphosphate / Q000138:chemical synthesis*; D008049:Lipase; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009904:Optical Rotation; D011549:Pseudomonas / Q000201:enzymology; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
D007202:Indicators and Reagents; C087383:2,3-O-cyclohexylidene-myo-inositol; D007294:Inositol; D015544:Inositol 1,4,5-Trisphosphate; D008049:Lipase