141315-50-6Relevant articles and documents
Efficient access to l-phenylglycine using a newly identified amino acid dehydrogenase from: Bacillus clausii
Cheng, Jun,Xu, Guochao,Han, Ruizhi,Dong, Jinjun,Ni, Ye
, p. 80557 - 80563 (2016)
An amino acid dehydrogenase from Bacillus clausii (BcAADH) was identified and overexpressed in Escherichia coli BL21(DE3) for the preparation of l-phenylglycine from benzoylformic acid. Recombinant BcAADH was purified to homogeneity and characterized. BcAADH could catalyse reductive amination and oxidative deamination at optimum pHs of 9.5 and 10.5. Furthermore, BcAADH has a broad substrate spectrum, displaying activities toward various aromatic and aliphatic keto acids. When coexpressed with glucose dehydrogenase from Bacillus megaterium, the potential application of BcAADH in the preparation of l-phenylglycine was investigated at a high substrate loading and low biocatalyst addition. As much as 400 mM benzoylformic acid could be fully reduced into l-phenylglycine within 6 h at >99.9% ee. With merely 0.5 g DCW L-1, 200 mM benzoylformic acid was completely reduced, resulting in a substrate to biocatalyst ratio of 60 g g-1, environmental factor of 4.7 and 91.7% isolation yield at gram scale. This study provides guidance for the application of BcAADH in the synthesis of chiral non-natural amino acids.
Resolution of racemic 2-chlorophenyl glycine with immobilized penicillin G acylase
Fadnavis, Nitin W.,Vedamayee Devi, Avala,Swarnalatha Jasti, Lakshmi
, p. 2363 - 2366 (2008)
Racemic 2-chlorophenyl glycine has been resolved to obtain (S)-α-amino-(2-chlorophenyl)acetic acid with >99% enantiomeric purity via enantioselective hydrolysis of its N-phenylacetyl derivative with penicillin G acylase immobilized on Eupergit C. The reso
Method for continuously and quickly preparing DL-phenylglycine and analogue thereof
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Paragraph 0031-0033, (2019/07/04)
The invention provides a method for continuously and quickly preparing DL-phenylglycine and an analogue thereof. The method comprises the steps of adding 2-hydroxyl-phenylacetonitrile and an analoguethereof (cyanohydrin for short) and an aqueous ammonium bicarbonate solution into a microchannel reactor for a reaction, controlling the reaction temperature to be 80-130 DEG C, and controlling the reaction pressure to be 0.5-2.0 MPa, wherein the standing time of the reactants in a microchannel is 1-8 min, and an aqueous solution of 5-phenyl-hydantoin and an analogue thereof (hydantoin for short)is obtained; adding the hydantoin and alkali into the microchannel reactor for a reaction, controlling the reaction temperature to be 120-200 DEG C, and controlling the reaction pressure to be 1.0-3.5MPa, wherein the standing time of the reactants in the microchannel is 1-8 min, and then a saline solution of phenylglycine and an analogue thereof is obtained; conducting acidification neutralization and crystallization to obtain the phenylglycine and the analogue thereof. According to the method, the microchannel reactor is adopted, the reaction time is greatly shorted, the reaction speed is increased, pyrolysis and polymerization of the cyanohydrin are reduced, no by-products are generated, the products are high in yield, clean and environmentally friendly, and the production cost is lowered.
Chemo-enzymatic approach to the synthesis of the antithrombotic clopidogrel
Ferraboschi, Patrizia,Mieri, Maria De,Galimberti, Fiorella
experimental part, p. 2136 - 2141 (2010/10/03)
The (S)-2-chlorophenylglycine moiety is well recognized in the structure of (S)-clopidogrel, a known antithrombotic drug. We prepared an enantiomerically pure chiral building block via an enzyme-catalyzed resolution of (RS)-N-Boc-2-chlorophenylglycine methylester. The best results were obtained by means of an immobilized subtilisin, the cross-linked enzyme aggregate (Alcalase-CLEA). The high enantiomeric excess of the synthon obtained remained the same over the course of clopidogrel synthesis; the simplicity of the process makes this pathway suitable for large-scale preparation.
