Whole-cell yeast-mediated preparation of (R)-2-chloro-1-(3-nitrophenyl) ethanol as a synthetic precursor for (R)-phenylephrine

Daisuke Tokoshima, Kengo Hanaya, Mitsuru Shoji, Takeshi Sugai

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)95-99
Number of pages5
JournalJournal of Molecular Catalysis B: Enzymatic
Volume97
DOIs
Publication statusPublished - 2013

Fingerprint

Adrenergic Agonists
Biocatalysts
Pichia
Poisons
Phenylephrine
Yeast
Ethanol
Yeasts
Crystalline materials
Substrates
Enzymes
N-methylaminoethanol
amberlite XAD 7

Keywords

  • α-Chloroarylethanone
  • Reduction
  • Whole-cell biocatalyst
  • Yeast

ASJC Scopus subject areas

  • Biochemistry
  • Bioengineering
  • Catalysis
  • Process Chemistry and Technology

Cite this

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title = "Whole-cell yeast-mediated preparation of (R)-2-chloro-1-(3-nitrophenyl) ethanol as a synthetic precursor for (R)-phenylephrine",
abstract = "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.",
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author = "Daisuke Tokoshima and Kengo Hanaya and Mitsuru Shoji and Takeshi Sugai",
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language = "English",
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journal = "Journal of Molecular Catalysis - B Enzymatic",
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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

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 - α-Chloroarylethanone

KW - Reduction

KW - Whole-cell biocatalyst

KW - Yeast

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JF - Journal of Molecular Catalysis - B Enzymatic

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