Enzymes in Organic Chemistry; Part 3: Enantioselective Hydrolysis of 1-Acyloxyalkylphosphonates by Lipase from Aspergillus niger (Lipase AP 6)
- 1 October 1995
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1995 (10) , 1267-1272
- https://doi.org/10.1055/s-1995-4083
Abstract
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.Keywords
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