Enzymes in Organic Chemistry; Part 3: Enantioselective Hydrolysis of 1-Acyloxyalkylphosphonates by Lipase from Aspergillus niger (Lipase AP 6)

All articles of this category Racemic α -acyloxyalkylphosphonates (±)- 4 are prepared and tested for kinetic resolution by lipases AP 6 and to a minor extent by F-AP 15. The former proves to be a useful enzyme in terms of broadness of application, reaction rate and enantiomeric excess. Lipase F-AP 15 transformed neither of the two substrates checked for hydrolysis. Enzymatic hydrolysis of α -acyloxyphosphonates containing straight chain alkyl groups with lipase AP 6 yields ( S)-α -hydroxyalkylphosphonates 3 preferentially. Substrates with branched chain alkyl groups are hydrolysed with lower enantioselectivity, the ( R )-ester being saponified more easily than the ( S )-ester. Optically active α -hydroxyalkylphosphonates are prepared using a lipase