The acetates of p-nitrophenyl alpha-L-arabinofuranoside--regioselective preparation by action of lipases.
All possible di-O-acetates and mono-O-acetates of p-nitrophenyl alpha-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 alpha-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 alpha-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 alpha-L-arabinofuranoside catalysed by porcine pancreas lipase. Finally, the 2- and 3-O-acetates of p-nitrophenyl alpha-L-arabinofuranoside were obtained in two steps. The enzymatic di-O-acetylation of p-nitrophenyl alpha-L-arabinofuranoside by LPS-30 was followed by enzymatic hydrolysis of the primary acetyl group by CCL or LAY.
Mastihubová
Mária
M
Institute of Chemistry, Slovak Academy of Sciences, SK-845 38 Bratislava, Slovakia. chemjama@savba.sk
Szemesová
Jana
J
Biely
Peter
P
D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry*; D000107:Acetylation; D001089:Arabinose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002175:Candida / Q000201:enzymology; D008049:Lipase / Q000737:chemistry*; D013237:Stereoisomerism
D000085:Acetates; C017567:4-nitrophenyl-alpha-L-arabinofuranoside; D001089:Arabinose; D008049:Lipase