The first direct enzymatic hydrolysis of alicyclic β-amino esters: A route to enantiopure cis and trans β-amino acids

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Abstract

The first direct enzymatic method is reported for the synthesis of cis and trans βamino acid enantiomers through the lipase-catalyzed enantioselective hydrolysis of alicyclic β esters in organic media. High enantioselectivities (E usually > 001) were observed when the Candida antarctica lipase B catalyzed reactions were performed with H2O (0.5 equivalents) in iP iPr2O at 5°C. The resolved products, obtained in good yields (≥42%), could be easily separated.

Original languageEnglish
Pages (from-to)6397-6401
Number of pages5
JournalChemistry - A European Journal
Volume13
Issue number22
DOIs
Publication statusPublished - 2007

Fingerprint

Enzymatic hydrolysis
Enantiomers
Enantioselectivity
Lipases
Lipase
Amino acids
Hydrolysis
Esters
Amino Acids
Candida
Candida antarctica lipase B

Keywords

  • Amino acids
  • Cispentacin
  • Enantioselectivity
  • Enzymes
  • Hydrolysis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "The first direct enzymatic method is reported for the synthesis of cis and trans βamino acid enantiomers through the lipase-catalyzed enantioselective hydrolysis of alicyclic β esters in organic media. High enantioselectivities (E usually > 001) were observed when the Candida antarctica lipase B catalyzed reactions were performed with H2O (0.5 equivalents) in iP iPr2O at 5°C. The resolved products, obtained in good yields (≥42{\%}), could be easily separated.",
keywords = "Amino acids, Cispentacin, Enantioselectivity, Enzymes, Hydrolysis",
author = "E. Forr{\'o} and F. F{\"u}l{\"o}p",
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T1 - The first direct enzymatic hydrolysis of alicyclic β-amino esters

T2 - A route to enantiopure cis and trans β-amino acids

AU - Forró, E.

AU - Fülöp, F.

PY - 2007

Y1 - 2007

N2 - The first direct enzymatic method is reported for the synthesis of cis and trans βamino acid enantiomers through the lipase-catalyzed enantioselective hydrolysis of alicyclic β esters in organic media. High enantioselectivities (E usually > 001) were observed when the Candida antarctica lipase B catalyzed reactions were performed with H2O (0.5 equivalents) in iP iPr2O at 5°C. The resolved products, obtained in good yields (≥42%), could be easily separated.

AB - The first direct enzymatic method is reported for the synthesis of cis and trans βamino acid enantiomers through the lipase-catalyzed enantioselective hydrolysis of alicyclic β esters in organic media. High enantioselectivities (E usually > 001) were observed when the Candida antarctica lipase B catalyzed reactions were performed with H2O (0.5 equivalents) in iP iPr2O at 5°C. The resolved products, obtained in good yields (≥42%), could be easily separated.

KW - Amino acids

KW - Cispentacin

KW - Enantioselectivity

KW - Enzymes

KW - Hydrolysis

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DO - 10.1002/chem.200700257

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