Improved enzymatic syntheses of valuable β-arylalkyl-β-amino acid enantiomers

Gábor Tasnádi, E. Forró, F. Fülöp

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The enantioselective (E∼ 200) Burkholderia cepacia-catalysed hydrolyses of β-amino esters with H2O (0.5 equiv.) in t-BuOMe or in i-Pr2O at 45 °C are described. The enantiomers of biologically relevant β-arylalkyl-substituted β-amino acids, and especially (R)-3-amino-3-(2,4,5-trifluorophenyl)butanoic acid, the intermediate of the new antidiabetic drug sitagliptine, were prepared with high enantiomeric excesses (ee≥96%) and in good yields (≥42%).

Original languageEnglish
Pages (from-to)793-799
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume8
Issue number4
DOIs
Publication statusPublished - 2010

Fingerprint

Burkholderia cepacia
Butyric Acid
Enantiomers
enantiomers
Hypoglycemic Agents
amino acids
hydrolysis
esters
Hydrolysis
Esters
drugs
Amino Acids
acids
synthesis

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

Improved enzymatic syntheses of valuable β-arylalkyl-β-amino acid enantiomers. / Tasnádi, Gábor; Forró, E.; Fülöp, F.

In: Organic and Biomolecular Chemistry, Vol. 8, No. 4, 2010, p. 793-799.

Research output: Contribution to journalArticle

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