171002-20-3Relevant academic research and scientific papers
Biocatalytic approach to enatiomerically pure β-amino acids
Soloshonok,Fokina,Rybakova,Shishkina,Galushko,Sorochinsky,Kukhar,Savchenko,Svedas
, p. 1601 - 1610 (1995)
β-Aryl-β-amino acids were prepared in good chemical yield and high enantiomeric purity (> 95% ee) via penicillin acylase-catalyzed hydrolysis of the corresponding N-phenylacetyl derivatives. The (R)-enantiomers were the fast-reacting isomers in all cases studied. The biocatalytic procedure described employs a very simple set of reactions using inexpensive commercially available chemicals and enzyme, and could be easily scaled up.
Enantioselective acylation of β-phenylalanine acid and its derivatives catalyzed by penicillin G acylase from alcaligenes faecalis
Li, Dengchao,Ji, Lilian,Wang, Xinfeng,Wei, Dongzhi
, p. 207 - 216 (2013/04/23)
This study developed a simple, efficient method for producing racemic β-phenylalanine acid (BPA) and its derivatives via the enantioselective acylation catalyzed by the penicillin G acylase from Alcaligenes faecalis (Af-PGA). When the reaction was run at 25°C and pH 10 in an aqueous medium containing phenylacetamide and BPA in a molar ratio of 2:1, 8 U/mL enzyme and 0.1 M BPA, the maximum BPA conversion efficiency at 40 min only reached 36.1%, which, however, increased to 42.9% as the pH value and the molar ratio of phenylacetamide to BPA were elevated to 11 and 3:1, respectively. Under the relatively optimum reaction conditions, the maximum conversion efficiencies of BPA derivatives all reached about 50% in a relatively short reaction time (45-90 min). The enantiomeric excess value of product (eep) and enantiomeric excess value of substrate (ees) were all above 98% and 95%, respectively. These results suggest that the method established in this study is practical, effective, and environmentally benign and may be applied to industrial production of enantiomerically pure BPA and its derivatives.
