Lipase-catalyzed acetylation of N-acetylneuraminic acid derivative.
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.
Lo
L C
LC
Department of Chemistry, National Taiwan University, Taipei.
Hsiao
K F
KF
Ueng
S H
SH
Wu
S H
SH
D000107:Acetylation; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D008049:Lipase / Q000378:metabolism*; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000378:metabolism*; D011549:Pseudomonas / Q000201:enzymology; D013997:Time Factors; D014753:Vinyl Compounds / Q000378:metabolism
D014753:Vinyl Compounds; D008049:Lipase; D019158:N-Acetylneuraminic Acid; C011566:vinyl acetate