The acetates of p-nitrophenyl α-l-arabinofuranoside—Regioselective preparation by action of lipases

All possible di-O-acetates and mono-O-acetates of p-nitrophenyl α-l-arabinofuranoside were prepared by chemoenzymatic way using lipases. The 2,3-di-O-acetate was obtained in 90% yield by deacetylation of the primary acetyl group of per-O-acetylated p-nitrophenyl α-l-arabinofuranoside by Candida cylindracea lipase (CCL) or Candida rugosa lipase (LAY). The 2,5- and 3,5-di-O-acetates were obtained by acetylation of p-nitrophenyl α-l-arabinofuranoside by Pseudomonas cepacia lipase (LPS-30) in organic solvents. The 5-O-acetate was regioselectively synthesised in 95% yield by acetylation of p-nitrophenyl α-l-arabinofuranoside catalysed by porcine pancreas lipase. Finally, the 2- and 3-O-acetates of p-nitrophenyl α-l-arabinofuranoside were obtained in two steps. The enzymatic di-O-acetylation of p-nitrophenyl α-l-arabinofuranoside by LPS-30 was followed by enzymatic hydrolysis of the primary acetyl group by CCL or LAY.

All possible di-O-acetates and mono-O-acetates of p-nitrophenyl α-l-arabinofuranoside were regioselectively prepared through acetylation or hydrolysis catalysed by lipases of various origin.Figure optionsDownload as PowerPoint slide