65414-83-7Relevant academic research and scientific papers
Asymmetric biocatalysis of S-3-amino-3-phenylpropionic acid with new isolated Methylobacterium Y1-6
Li, Yi,Wang, Wenfu,Huang, Yumian,Zou, Qianwen,Zheng, Guojun
, p. 1674 - 1678 (2013/11/19)
β-amino acids are widely used in drug research, and S-3-amino-3-phenylpropionic acid (S-APA) is an important pharmaceutical intermediate of S-dapoxetine, which has been approved for the treatment of premature ejaculation. Chiral catalysis is an excellent method for the preparation of enantiopure compounds. In this study, we used (±)-ethyl-3-amino-3-phenylpropanoate (EAP) as the sole carbon source. Three hundred thirty one microorganisms were isolated from 30 soil samples, and 17 strains could produce S-APA. After three rounds of cultivation and identification, the strain Y1-6 exhibiting the highest enantioselective activity of S-APA was identified as Methylobacterium oryzae. The optimal medium composition contained methanol (2.5 g/L), 1,2-propanediol (7.5 g/L), soluble starch (2.5 g/L), and peptone (10 g/L); it was shaken at 220 rpm for 4-5 days at 30 C. The optimum condition for biotransformation of EAP involved cultivation at 37 C for 48 h with 120 mg of wet cells and 0.64 mg of EAP in 1 ml of transfer solution. Under this condition, substrate ee was 92.1% and yield was 48.6%. We then attempted to use Methylobacterium Y1-6 to catalyze the hydrolytic reaction with substrates containing 3-amino-3-phenyl-propanoate ester, N-substituted-β-ethyl-3-amino-3-phenyl-propanoate, and γ-lactam. It was found that 5 compounds with ester bonds could be stereoselectively hydrolyzed to S-acid, and 2 compounds with γ-lactam bonds could be stereoselectively hydrolyzed to (-)-γ-lactam.
Development of a commercial process for (S)-β-phenylalanine (1)
Grayson, J. Ian,Roos, Juergen,Osswald, Steffen
, p. 1201 - 1206 (2011/12/16)
The development of a commercial manufacturing route for (S)-β-phenylalanine 8, a key pharmaceutical building block, is described. The different approaches which were investigated, based on catalytic asymmetric hydrogenation of enamide intermediates and on biocatalysis using acylase and lipase hydrolyses, are compared. The lipase resolution route was chosen for scale-up, and the final two-step process, based on readily available raw materials, is shown to be robust at full manufacturing scale
An expedient synthesis of 6-arylpiperidine-2,4-diones by chain-extension of β-aryl-β-aminoacids
Leflemme, Nicolas,Dallemagne, Patrick,Rault, Sylvain
, p. 8997 - 8999 (2007/10/03)
The synthesis of novel 6-arylpiperidine-2,4-diones is described in five steps starting from β-aryl-β-aminoacids via the chain extension of the latter into δ-aryl-δ-amino-β-ketoacids. The chemical pathway involves an acylation of Meldrum's acid and yields useful building blocks for heterocyclic chemistry.
Biocatalytic approach to enatiomerically pure β-amino acids
Soloshonok,Fokina,Rybakova,Shishkina,Galushko,Sorochinsky,Kukhar,Savchenko,Svedas
, p. 1601 - 1610 (2007/10/02)
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.
