5856-62-2Relevant articles and documents
A mild and highly efficient synthesis of chiral N-dichloroacetyl-4-ethyl-1, 3-oxazolidines
Zhao, Li-Xia,Fu, Ying,Ye, Fei,Gao, Shuang
, p. 943 - 946 (2012)
Chiral 2-amino-butanols (4 and 5) were obtained via the isolation of diastereomeric salt. Then, chiral compounds (6-9) were synthesized by a sequential procedure involving condensation of chiral 2-amino-butanol with ketone and dichloroacetyl chloride. All the compounds were characterized by IR, 1H NMR, 13C NMR, and element analysis. The absolute configurations of (S)-8 was determined by X-ray crystallography.
Enantioselective Cascade Biocatalysis for Deracemization of Racemic β-Amino Alcohols to Enantiopure (S)-β-Amino Alcohols by Employing Cyclohexylamine Oxidase and ω-Transaminase
Zhang, Jian-Dong,Chang, Ya-Wen,Dong, Rui,Yang, Xiao-Xiao,Gao, Li-Li,Li, Jing,Huang, Shuang-Ping,Guo, Xing-Mei,Zhang, Chao-Feng,Chang, Hong-Hong
, p. 124 - 128 (2020/09/21)
Optically active β-amino alcohols are very useful chiral intermediates frequently used in the preparation of pharmaceutically active substances. Here, a novel cyclohexylamine oxidase (ArCHAO) was identified from the genome sequence of Arthrobacter sp. TYUT010-15 with the R-stereoselective deamination activity of β-amino alcohol. ArCHAO was cloned and successfully expressed in E. coli BL21, purified and characterized. Substrate-specific analysis revealed that ArCHAO has high activity (4.15 to 6.34 U mg?1 protein) and excellent enantioselectivity toward the tested β-amino alcohols. By using purified ArCHAO, a wide range of racemic β-amino alcohols were resolved, (S)-β-amino alcohols were obtained in >99 % ee. Deracemization of racemic β-amino alcohols was conducted by ArCHAO-catalyzed enantioselective deamination and transaminase-catalyzed enantioselective amination to afford (S)-β-amino alcohols in excellent conversion (78–94 %) and enantiomeric excess (>99 %). Preparative-scale deracemization was carried out with 50 mM (6.859 g L?1) racemic 2-amino-2-phenylethanol, (S)-2-amino-2-phenylethanol was obtained in 75 % isolated yield and >99 % ee.
Selective hydrogenation of primary amides and cyclic di-peptides under Ru-catalysis
Subaramanian, Murugan,Sivakumar, Ganesan,Babu, Jessin K.,Balaraman, Ekambaram
supporting information, p. 12411 - 12414 (2020/10/30)
A ruthenium(II)-catalyzed selective hydrogenation of challenging primary amides and cyclic di-peptides to their corresponding primary alcohols and amino alcohols, respectively, is reported. The hydrogenation reaction operates under mild and eco-benign conditions and can be scaled-up.
Enantioselective Synthesis of Chiral Vicinal Amino Alcohols Using Amine Dehydrogenases
Chen, Fei-Fei,Cosgrove, Sebastian C.,Birmingham, William R.,Mangas-Sanchez, Juan,Citoler, Joan,Thompson, Matthew P.,Zheng, Gao-Wei,Xu, Jian-He,Turner, Nicholas J.
, p. 11813 - 11818 (2019/12/02)
Chiral vicinal amino alcohols are an important motif found in many biologically active molecules. In this study, biocatalytic reductive amination of α-hydroxy ketones with ammonia was investigated using engineered amine dehydrogenases (AmDHs) derived from the leucine amino acid dehydrogenase (AADH) from Lysinibacillus fusiformis. The AmDHs thus identified enabled the synthesis of (S)-configured vicinal amino alcohols from the corresponding α-hydroxy ketones in up to 99% conversions and >99% ee. One of the AmDH variants was used to prepare a key intermediate for the antituberculosis pharmaceutical ethambutol.