Biocatalysis for the preparation of optically active β-lactam precursors of amino acids

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

Research output: Contribution to journalArticle

63 Citations (Scopus)

Abstract

Enantioselective acylation of N-hydroxymethylated β-lactams in the presence of Pseudomonas sp. lipase afforded optically active precursors for the preparation of (1R,2S)- and (1S,2R)-2-aminocyclopentane- and (1R,2S,3R,4S)- and (1S,2R,3S,4R)-3-aminobicyclo[2.2.1]heptanecarboxylic acids. Due to the high enantioselectivity (E = 90 and 62) and in order to minimize the enzymatic hydrolysis of the acylated products back to the starting alcohol, the reactions were performed in acetone.

Original languageEnglish
Pages (from-to)1789-1796
Number of pages8
JournalTetrahedron Asymmetry
Volume7
Issue number6
DOIs
Publication statusPublished - Jun 1996

Fingerprint

Biocatalysis
acylation
Lactams
Acylation
pseudomonas
Enzymatic hydrolysis
Enantioselectivity
Lipases
Acetone
Pseudomonas
Lipase
acetone
amino acids
hydrolysis
Amino acids
Hydrolysis
alcohols
Alcohols
Amino Acids
preparation

ASJC Scopus subject areas

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

Cite this

Biocatalysis for the preparation of optically active β-lactam precursors of amino acids. / Csomós, P.; Kanerva, Liisa T.; Bernáth, G.; Fülöp, F.

In: Tetrahedron Asymmetry, Vol. 7, No. 6, 06.1996, p. 1789-1796.

Research output: Contribution to journalArticle

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