614-19-7Relevant articles and documents
Preparation methods of beta-azido acid and beta-amino acid compounds and application thereof
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, (2021/10/20)
The invention discloses a preparation method of beta-azido acid, which comprises the following step of: carrying out a reaction on an ethylene compound, CZ1Z2Z3Z4 and trimethylsilyl azide as initial raw materials to obtain the beta-azido acid. The ethylene compound has a structural general formula as shown in a formula I, and the beta-azido acid has a structural general formula as shown in a formula II, wherein R is selected from one of alkyl, substituted alkyl, heteroaryl and substituted heteroaryl; and Z1, Z2, Z3 and Z4 are respectively and independently at least one selected from fluorine, chlorine, bromine and iodine. The invention further provides beta-amino acid and application of the preparation method. The preparation methods of the beta-azido acid and the beta-amino acid, provided by the invention, have the advantages of cheap raw materials and catalysts, mild reaction conditions, simplicity in operation, high reaction efficiency and the like.
Characterization of a new nitrilase from Hoeflea phototrophica DFL-43 for a two-step one-pot synthesis of (S)-β-amino acids
Zhang, Zhi-Jun,Cai, Rui-Feng,Xu, Jian-He
, p. 6047 - 6056 (2018/05/15)
A nitrilase from Hoeflea phototrophica DFL-43 (HpN) demonstrating excellent catalytic activity towards benzoylacetonitrile was identified from a nitrilase tool-box, which was developed previously in our laboratory for (R)-o-chloromandelic acid synthesis from o-chloromandelonitrile. The HpN was overexpressed in Escherichia coli BL21 (DE3), purified to homogeneity by nickel column affinity chromatography, and its biochemical properties were studied. The HpN was very stable at 30–40?°C, and highly active over a wide range of pH values (pH 6.0–10.0). In addition, the HpN could tolerate against several hydrophilic organic solvents. Steady-state kinetics indicated that HpN was highly active towards benzoylacetonitrile, giving a KM of 4.2?mM and a kcat of 170?s?1, the latter of which is ca. fivefold higher than the highest record reported so far. A cascade reaction for the synthesis of optically pure (S)-β-phenylalanine from benzoylacetonitrile was developed by coupling HpN with an ω-transaminase from Polaromonas sp. JS666 in toluene-water biphasic reaction system using β-alanine as an amino donor. Various (S)-β-amino acids could be produced from benzoylacetonitrile derivatives with moderate to high conversions (73–99%) and excellent enantioselectivity (> 99% ee). These results are significantly advantageous over previous studies, indicating a great potential of this cascade reaction for the practical synthesis of (S)-β-phenylalanine in the future.
Synthetic method for novel chiral ligand, metal chelate, multiple unnatural amino acids, maraviroc and key intermediate thereof
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Paragraph 0490-0492, (2018/04/26)
The invention discloses a synthetic method for a novel chiral ligand, a metal chelate, multiple unnatural amino acids, maraviroc and a key intermediate thereof. According to the synthetic method, (R)-2-methylproline is selected as a starting material, and asymmetrical resolution is induced by utilizing a nickel chelate, so that (S)-beta3-amino acid is obtained, and (S)-3-amino-3-phenylpropionic acid is taken as the key intermediate for synthesizing maraviroc, so that yield is high, and ee value reaches more than or equal to 98.2%. The method disclosed by the invention has the advantages that source of raw materials is wide, conditions of a synthetic process are mild, control is easy, and optical purity of products is high.
