title: Chemo-enzymatic Synthesis of both Enantiomers of myo-Inositol 1,3,4,5-tetrakisphosphate.
abstract: D-Ins(1,3,4,5)P4 and unnatural L-Ins(1,3,4,5)P4 were prepared in gram-quantities from D- and L-2,6-di-O-benzyl-myo-inositol by a chemical phosphorylation and deprotection step in high yield and purity without extensive purification. The optically pure benzyl derivatives were obtained by enzyme-catalyzed resolution of racemic 2,6-di-O-benzyl-myo-inositol under acyl-transfer conditions in vinyl acetate as the acyl donor. The lipase of Candida antarctica only acetylated regio- and enantio-selectively the L-enantiomer, providing exclusively L-5-acetyl-2,6-di-O-benzyl-myo-inositol, whereas the D-enantiomer remained unchanged.
authors.affiliation: a Novartis Pharma AG, Core Technology Area.
authors.forename: K
authors.initials: K
authors.lastname: Laumen
authors.affiliation: a Novartis Pharma AG, Core Technology Area.
authors.forename: O
authors.initials: O
authors.lastname: Ghisalba
keywords: Candida antarctica; D-myo-inositol 1,3,4,5-tetrakisphosphate; L-myo-inositol 1,3,4,5-tetrakisphosphate; enzymatic esterification; lipase