A convenient synthesis of D-myo-inositol 1,4,5-trisphosphate (Ins(1,4,5)P3) and L-myo-inositol 1,4,5-trisphosphate (Ins(3,5,6)P3).
An efficient synthesis of an optically active inositol derivative that is a precursor to D-myo-inositol 1,4,5-trisphosphate (Ins(1,4,5)P3, (-)) is described. Crystallization of the diastereomers of (+/-)-1-O-[(+)-menthoxycarbonyl]-6-O-benzyl-2,3:4,5-di-O-isopropyl idene-myo- inositol diastereomers from methanol gives only one diastereomer. Alkaline hydrolysis gives the useful inositol derivative (-)-6-O-benzyl-2,3:4,5-di-O-isopropylidene-myo-inositol. Likewise, crystallization of the diastereomers of (+/-)-3-O-[(-)-menthoxycarbonyl]-4-O-benzyl-1,2:5,6-di-O-isopropyl idene-myo- inositol from methanol gave a pure compound which could be hydrolyzed to give (+)-4-O-benzyl-1,2:5,6-di-O-isopropylidene-myo-inositol, a precursor to D-myo-inositol 3,5,6-trisphosphate (Ins(3,5,6)P3,(+)). The ease with which these enantiomerically pure inositol derivatives were isolated may facilitate the synthesis of more complex inositol phosphate derivatives such as D-myo-inositol 1,3,4,5-tetrakisphosphate.
Leung
L W
LW
Department of Chemistry and Biochemistry, Queens College of the City University of New York, Flushing 11367-1597, USA.
Bittman
R
R
D015544:Inositol 1,4,5-Trisphosphate / Q000138:chemical synthesis*; D019906:Nuclear Magnetic Resonance, Biomolecular; D011522:Protons; D013237:Stereoisomerism
D011522:Protons; D015544:Inositol 1,4,5-Trisphosphate