TY - JOUR
T1 - Whole-cell yeast-mediated preparation of (R)-2-chloro-1-(3-nitrophenyl) ethanol as a synthetic precursor for (R)-phenylephrine
AU - Tokoshima, Daisuke
AU - Hanaya, Kengo
AU - Shoji, Mitsuru
AU - Sugai, Takeshi
N1 - Funding Information:
We thank Mr. Shohei Taketomi for his discussion on the early stage of this work. This work was supported both by a Grant-in-Aid for Scientific Research (No. 23580152 ) and Platform for Drug Discovery, Informatics, and Structural Life Science from the Ministry of Education, Culture, Sports, Science and Technology, Japan , and acknowledged with thanks.
PY - 2013
Y1 - 2013
N2 - The incubated whole-cell biocatalyst of Pichia minuta JCM 3622 reduced 2-chloro-1-(3-nitrophenyl)ethanone to provide (R)-2-chloro-1-(3-nitrophenyl) ethanol with 99.2% ee in 87% isolated yield in the presence of Amberlite XAD-7 as a reservoir for the hydrophobic, crystalline and toxic substrate. The product was transformed to (R)-1-(3-hydroxyphenyl)-2-methylaminoethanol (phenylephrine, 1a), a selective α1-adrenergic receptor agonist, in 98.0% ee over five steps.
AB - The incubated whole-cell biocatalyst of Pichia minuta JCM 3622 reduced 2-chloro-1-(3-nitrophenyl)ethanone to provide (R)-2-chloro-1-(3-nitrophenyl) ethanol with 99.2% ee in 87% isolated yield in the presence of Amberlite XAD-7 as a reservoir for the hydrophobic, crystalline and toxic substrate. The product was transformed to (R)-1-(3-hydroxyphenyl)-2-methylaminoethanol (phenylephrine, 1a), a selective α1-adrenergic receptor agonist, in 98.0% ee over five steps.
KW - Reduction
KW - Whole-cell biocatalyst
KW - Yeast
KW - α-Chloroarylethanone
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U2 - 10.1016/j.molcatb.2013.07.021
DO - 10.1016/j.molcatb.2013.07.021
M3 - Article
AN - SCOPUS:84883151820
SN - 1381-1177
VL - 97
SP - 95
EP - 99
JO - Journal of Molecular Catalysis - B Enzymatic
JF - Journal of Molecular Catalysis - B Enzymatic
ER -