Lipase-catalyzed acetylation of N-acetylneuraminic acid derivative

Bioorg Med Chem Lett. 1999 Mar 8;9(5):709-12. doi: 10.1016/s0960-894x(99)00060-8.

Abstract

A facile preparation of triacetylated derivative of 2-phenylthioglycoside of N-acetylneuraminic acid (4) was achieved by treatment with lipase PS in vinyl acetate. The major product 4 has a free hydroxyl group at C-7. Results of time-course HPLC analysis indicate that the reactivity of the hydroxyl groups under this condition is in the following order; C-9 > C-4 > C-8 > C-7.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Catalysis
  • Chromatography, High Pressure Liquid
  • Lipase / metabolism*
  • N-Acetylneuraminic Acid / analogs & derivatives
  • N-Acetylneuraminic Acid / chemical synthesis
  • N-Acetylneuraminic Acid / metabolism*
  • Pseudomonas / enzymology
  • Time Factors
  • Vinyl Compounds / metabolism

Substances

  • Vinyl Compounds
  • Lipase
  • N-Acetylneuraminic Acid
  • vinyl acetate