Lipase-catalyzed regio- and enantioselective esterification of rac-1,2-O-cyclohexylidene-myo-inositol

Marco T. Rudolf, Carsten Schultz

Research output: Contribution to journalArticle

9 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)533-537
Number of pages5
JournalLiebigs Annales
Issue number4
StatePublished - Apr 1996
Externally publishedYes

Fingerprint

Esterification
Inositol
Lipase
Hydroxyl Radical
Organic solvents
2,3-O-cyclohexylidene-myo-inositol
vinyl acetate
inositol-1,4,5,6-tetrakisphosphate
inositol 1,4,6-trisphosphate
2,2,2-trifluoroethyl butyrate

Keywords

  • Enzyme-catalyzed esterification
  • Lipases
  • myo-Inositol 1,4,5,6-tetrakisphosphate
  • myo-Inositol 1,4,6-trisphosphate
  • Regio- and enantioselectivity

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Lipase-catalyzed regio- and enantioselective esterification of rac-1,2-O-cyclohexylidene-myo-inositol. / Rudolf, Marco T.; Schultz, Carsten.

In: Liebigs Annales, No. 4, 04.1996, p. 533-537.

Research output: Contribution to journalArticle

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N2 - 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).

AB - 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).

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