Enantioselective hydrolysis of some 3-(2-nitrophenoxy) butanoates catalyzed by Pseudomonas fluorescens and Pseudomonas sp. lipase

Snježana Knezović, Vitomir Šunjić, A. Lévai

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Racemic methyl, ethyl and cyanomethyl 3-(2′-nitrophenoxy) butanoates 4-10, chiral precursors of 2,3-dihydro-1,5-benzoxazepin-4(5H)-ones with ACE inhibitory activity, were prepared and submitted to kinetic resolution, by a series of commercially available lipases. Best results (e.e.'s ≫99%) were obtained with Pseudomonas fluorescens and Pseudomonas sp. lipase. The structure of the alkyl ester group influences the rate of hydrolysis. Cyanomethyl esters 5 and 8 were more reactive than alkyl esters 4, 6, 7, 9 and 10. Chiral 1H-NMR shift reagents revealed 70-90 % e.e. for the remaining R-(-)-esters in hydrolyses of rac. 4, 6, and 9, and ≫/99 % e.e. in hydrolyses of rac. 7 and 10. A large effect on the rate and enantioselectivity of the hydrolysis of esters 4, 6, and 9, is observed when a methyl group, which is remote from the chiral center and from the reactive ester group, is on the aromatic ring.

Original languageEnglish
Pages (from-to)313-320
Number of pages8
JournalTetrahedron Asymmetry
Volume4
Issue number3
DOIs
Publication statusPublished - 1993

Fingerprint

Pseudomonas fluorescens
pseudomonas
Lipases
Pseudomonas
Lipase
hydrolysis
esters
Hydrolysis
Esters
Enantioselectivity
reagents
Nuclear magnetic resonance
nuclear magnetic resonance
Kinetics
rings
shift
kinetics

Keywords

  • enzymatic kinetic resolution
  • Esters of 3-(2′-nitrophenoxy) butanoic acid
  • structure vs. rate and enantioselectivity of hydrolysis

ASJC Scopus subject areas

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

Cite this

Enantioselective hydrolysis of some 3-(2-nitrophenoxy) butanoates catalyzed by Pseudomonas fluorescens and Pseudomonas sp. lipase. / Knezović, Snježana; Šunjić, Vitomir; Lévai, A.

In: Tetrahedron Asymmetry, Vol. 4, No. 3, 1993, p. 313-320.

Research output: Contribution to journalArticle

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AU - Lévai, A.

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AB - Racemic methyl, ethyl and cyanomethyl 3-(2′-nitrophenoxy) butanoates 4-10, chiral precursors of 2,3-dihydro-1,5-benzoxazepin-4(5H)-ones with ACE inhibitory activity, were prepared and submitted to kinetic resolution, by a series of commercially available lipases. Best results (e.e.'s ≫99%) were obtained with Pseudomonas fluorescens and Pseudomonas sp. lipase. The structure of the alkyl ester group influences the rate of hydrolysis. Cyanomethyl esters 5 and 8 were more reactive than alkyl esters 4, 6, 7, 9 and 10. Chiral 1H-NMR shift reagents revealed 70-90 % e.e. for the remaining R-(-)-esters in hydrolyses of rac. 4, 6, and 9, and ≫/99 % e.e. in hydrolyses of rac. 7 and 10. A large effect on the rate and enantioselectivity of the hydrolysis of esters 4, 6, and 9, is observed when a methyl group, which is remote from the chiral center and from the reactive ester group, is on the aromatic ring.

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