Approach to highly enantiopure β-amino acid esters by using lipase catalysis in organic media

Liisa T. Kanerva, P. Csomós, Oskari Sundholm, G. Bernáth, F. Fülöp

Research output: Contribution to journalArticle

103 Citations (Scopus)

Abstract

Ethyl esters of ten alicyclic β-aminocarboxylic acids were resolved by lipase catalysis in organic solvents. The resolution was based on acylation of the amino group at the R-stereogenic centre with various 2,2,2- trifluoroethyl esters. An increase in the hydrophobic nature of the acyl donor enhanced the enantioselectivity and reactivity in the case of lipase SP 526 from Candida antarctica, while the opposite effect was observed with lipase PS from Pseudomonas cepacia. An unexceptional enantioselectivity enhancement was observed when 2,2,2-trifluoroethyl chloroacetate was used in the case of lipase PS catalysis.

Original languageEnglish
Pages (from-to)1705-1716
Number of pages12
JournalTetrahedron Asymmetry
Volume7
Issue number6
DOIs
Publication statusPublished - Jun 1996

Fingerprint

Lipases
Lipase
Catalysis
catalysis
amino acids
Amino acids
esters
Esters
Amino Acids
acylation
pseudomonas
Enantioselectivity
Antarctic regions
reactivity
Aminoacylation
Burkholderia cepacia
Acylation
acids
augmentation
Candida

ASJC Scopus subject areas

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

Cite this

Approach to highly enantiopure β-amino acid esters by using lipase catalysis in organic media. / Kanerva, Liisa T.; Csomós, P.; Sundholm, Oskari; Bernáth, G.; Fülöp, F.

In: Tetrahedron Asymmetry, Vol. 7, No. 6, 06.1996, p. 1705-1716.

Research output: Contribution to journalArticle

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