Lipase-catalysed kinetic resolution in organic solvents: An approach to enantiopure α-methyl-β-alanine esters

Magdolna Solymár, Arto Liljeblad, L. Lázár, F. Fülöp, Liisa T. Kanerva

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

The Candida antarctica lipase A (CAL-A) and B (CAL-B)-catalysed resolutions of α-methyl-β-alanine ethyl ester 1 with neat ethyl and butyl butanoates and with 2,2,2-trifluoroethyl butanoate in organic solvents were studied, as were the alcoholyses in neat butanol and with methanol (0.8 M) in diisopropyl ether. The two enzymes, which display opposite (S for CAL-A and R for CAL-B) and low enantioselectivities (E=7-10), allowed the preparation of the two enantiomers in a two-step resolution protocol. The R enantiomer (ee=97%) was first separated as its Boc-protected derivative from the CAL-A-catalysed resolution mixture of (R)-1 and the enantiomerically enriched N-butanoylated counterpart. The enantiopurification of the latter gave the S enantiomer (ee=96%) in the following CAL-B-catalysed 'interesterification' in butyl butanoate.

Original languageEnglish
Pages (from-to)1923-1928
Number of pages6
JournalTetrahedron Asymmetry
Volume13
Issue number17
DOIs
Publication statusPublished - Sep 9 2002

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Enzyme kinetics
Enantiomers
Candida
enantiomers
Lipases
Antarctic regions
alanine
Lipase
Organic solvents
esters
Esters
Butanols
Kinetics
kinetics
Methanol
Enantioselectivity
Butenes
Alanine
enzymes
Ethers

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Lipase-catalysed kinetic resolution in organic solvents : An approach to enantiopure α-methyl-β-alanine esters. / Solymár, Magdolna; Liljeblad, Arto; Lázár, L.; Fülöp, F.; Kanerva, Liisa T.

In: Tetrahedron Asymmetry, Vol. 13, No. 17, 09.09.2002, p. 1923-1928.

Research output: Contribution to journalArticle

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