Enzymes in organic chemistry; Part 3: Enantioselective hydrolysis of 1-acyloxyalkylphosphonates by lipase from Aspergillus niger (lipase AP 6)

Article abstract of DOI:10.1055/s-1995-4083

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 P-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.