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Synthesis 1995; 1995(10): 1267-1272
DOI: 10.1055/s-1995-4083
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Enzymes in Organic Chemistry; Part 3: Enantioselective Hydrolysis of 1-Acyloxyalkylphosphonates by Lipase from Aspergillus niger (Lipase AP 6)

Martina Drescher, F. Hammerschmidt* , Hanspeter Kählig
  • *Institut für Organische Chemie der Universität Wien, Währingerstraße 38, A-1090 Wien, Austria
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Publikationsdatum:
31. Dezember 2000 (online)

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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