A new route to enantiopure β-aryl-substituted β-amino acids and 4-aryl-substituted β-lactams through lipase-catalyzed enantioselective ring cleavage of β-lactams

E. Forró, Tihamér Paál, Gábor Tasnádi, F. Fülöp

Research output: Contribution to journalArticle

44 Citations (Scopus)

Abstract

A simple and efficient direct enzymatic method was developed for the synthesis of 4-aryl-substituted β-lactams and the corresponding β-amino acid enantiomers through the CAL-B (lipase B from Candida antarctica)-catalyzed enantioselective (E > 200) ring cleavage of the corresponding racemic β-lactams with 1 equiv. of H2O in i-Pr2O at 60°C. The product (R)-β-amino acids (ee ≥ 98%, yields ≥ 42%) and unreacted (S)-β-lactams (ee ≥ 95%, yields ≥ 41%) could be easily separated. The ring opening of enantiomeric β-lactams with 18% HCl afforded the corresponding enantiopure β-amino acid hydrochlorides (ee ≥ 99%).

Original languageEnglish
Pages (from-to)917-923
Number of pages7
JournalAdvanced Synthesis and Catalysis
Volume348
Issue number7-8
DOIs
Publication statusPublished - May 2006

Fingerprint

Lactams
Lipases
Lipase
Amino acids
Amino Acids
Enantiomers
Candida

Keywords

  • β-aryl-substituted β-amino acids
  • 4-aryl-substituted β-lactams
  • Enantioselectivity
  • Enzyme catalysis
  • Lipase
  • Ring cleavage

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Organic Chemistry
  • Catalysis

Cite this

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title = "A new route to enantiopure β-aryl-substituted β-amino acids and 4-aryl-substituted β-lactams through lipase-catalyzed enantioselective ring cleavage of β-lactams",
abstract = "A simple and efficient direct enzymatic method was developed for the synthesis of 4-aryl-substituted β-lactams and the corresponding β-amino acid enantiomers through the CAL-B (lipase B from Candida antarctica)-catalyzed enantioselective (E > 200) ring cleavage of the corresponding racemic β-lactams with 1 equiv. of H2O in i-Pr2O at 60°C. The product (R)-β-amino acids (ee ≥ 98{\%}, yields ≥ 42{\%}) and unreacted (S)-β-lactams (ee ≥ 95{\%}, yields ≥ 41{\%}) could be easily separated. The ring opening of enantiomeric β-lactams with 18{\%} HCl afforded the corresponding enantiopure β-amino acid hydrochlorides (ee ≥ 99{\%}).",
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author = "E. Forr{\'o} and Tiham{\'e}r Pa{\'a}l and G{\'a}bor Tasn{\'a}di and F. F{\"u}l{\"o}p",
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T1 - A new route to enantiopure β-aryl-substituted β-amino acids and 4-aryl-substituted β-lactams through lipase-catalyzed enantioselective ring cleavage of β-lactams

AU - Forró, E.

AU - Paál, Tihamér

AU - Tasnádi, Gábor

AU - Fülöp, F.

PY - 2006/5

Y1 - 2006/5

N2 - A simple and efficient direct enzymatic method was developed for the synthesis of 4-aryl-substituted β-lactams and the corresponding β-amino acid enantiomers through the CAL-B (lipase B from Candida antarctica)-catalyzed enantioselective (E > 200) ring cleavage of the corresponding racemic β-lactams with 1 equiv. of H2O in i-Pr2O at 60°C. The product (R)-β-amino acids (ee ≥ 98%, yields ≥ 42%) and unreacted (S)-β-lactams (ee ≥ 95%, yields ≥ 41%) could be easily separated. The ring opening of enantiomeric β-lactams with 18% HCl afforded the corresponding enantiopure β-amino acid hydrochlorides (ee ≥ 99%).

AB - A simple and efficient direct enzymatic method was developed for the synthesis of 4-aryl-substituted β-lactams and the corresponding β-amino acid enantiomers through the CAL-B (lipase B from Candida antarctica)-catalyzed enantioselective (E > 200) ring cleavage of the corresponding racemic β-lactams with 1 equiv. of H2O in i-Pr2O at 60°C. The product (R)-β-amino acids (ee ≥ 98%, yields ≥ 42%) and unreacted (S)-β-lactams (ee ≥ 95%, yields ≥ 41%) could be easily separated. The ring opening of enantiomeric β-lactams with 18% HCl afforded the corresponding enantiopure β-amino acid hydrochlorides (ee ≥ 99%).

KW - β-aryl-substituted β-amino acids

KW - 4-aryl-substituted β-lactams

KW - Enantioselectivity

KW - Enzyme catalysis

KW - Lipase

KW - Ring cleavage

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