Abstract
Whole-cell yeasts and mold-catalyzed reduction of two fluorinated acetophenone derivatives with very bulky substituents on ortho position of aromatic ring, (±)-1′-(2-tert-butyl-2-methyl-1,3-benzodioxol-4-yl)- 2′,2′-difluoroethanone and (±)-1′-(2-tert-butyl-2- methyl-1,3-benzodioxol-4-yl)-2′,2′,2′-trifluoroethanone were examined. On the former substrate, Geotrichum candidum NBRC 5767 showed high re-facially selective attack of hydride, while with Pichia angusta JCM 3620, complementary si-facially selective attack proceeded. G. candidum NBRC 5767 was revealed to be potent biocatalyst which provides (1′S)-alcohols from both substrates in a highly facially selective manner. Some unknown reductases were suggested responsible for those reductions, other than so far having been reported acetophenone reductase and trifluoromethyl ketone reductase from G. candidum, comparing the results obtained by applying those enzymes.
| Original language | English |
|---|---|
| Pages (from-to) | 86-91 |
| Number of pages | 6 |
| Journal | Journal of Molecular Catalysis B: Enzymatic |
| Volume | 82 |
| DOIs | |
| Publication status | Published - 2012 Oct |
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Keywords
- Asymmetric reduction
- Fluoroketone
- Fungi
- Isolated enzymes
- Stereochemistry
- Yeast
ASJC Scopus subject areas
- Biochemistry
- Bioengineering
- Catalysis
- Process Chemistry and Technology
Cite this
Reduction of acetophenones with methyl fluorines and a bulky group on the aromatic ring using microorganisms and related enzymes. / Abe, Chika; Sugawara, Takahiro; MacHida, Takuya; Higashi, Toshinori; Hanaya, Kengo; Shoji, Mitsuru; Cao, Chen; Yamamoto, Takuro; Matsuda, Tomoko; Sugai, Takeshi.
In: Journal of Molecular Catalysis B: Enzymatic, Vol. 82, 10.2012, p. 86-91.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Reduction of acetophenones with methyl fluorines and a bulky group on the aromatic ring using microorganisms and related enzymes
AU - Abe, Chika
AU - Sugawara, Takahiro
AU - MacHida, Takuya
AU - Higashi, Toshinori
AU - Hanaya, Kengo
AU - Shoji, Mitsuru
AU - Cao, Chen
AU - Yamamoto, Takuro
AU - Matsuda, Tomoko
AU - Sugai, Takeshi
PY - 2012/10
Y1 - 2012/10
N2 - Whole-cell yeasts and mold-catalyzed reduction of two fluorinated acetophenone derivatives with very bulky substituents on ortho position of aromatic ring, (±)-1′-(2-tert-butyl-2-methyl-1,3-benzodioxol-4-yl)- 2′,2′-difluoroethanone and (±)-1′-(2-tert-butyl-2- methyl-1,3-benzodioxol-4-yl)-2′,2′,2′-trifluoroethanone were examined. On the former substrate, Geotrichum candidum NBRC 5767 showed high re-facially selective attack of hydride, while with Pichia angusta JCM 3620, complementary si-facially selective attack proceeded. G. candidum NBRC 5767 was revealed to be potent biocatalyst which provides (1′S)-alcohols from both substrates in a highly facially selective manner. Some unknown reductases were suggested responsible for those reductions, other than so far having been reported acetophenone reductase and trifluoromethyl ketone reductase from G. candidum, comparing the results obtained by applying those enzymes.
AB - Whole-cell yeasts and mold-catalyzed reduction of two fluorinated acetophenone derivatives with very bulky substituents on ortho position of aromatic ring, (±)-1′-(2-tert-butyl-2-methyl-1,3-benzodioxol-4-yl)- 2′,2′-difluoroethanone and (±)-1′-(2-tert-butyl-2- methyl-1,3-benzodioxol-4-yl)-2′,2′,2′-trifluoroethanone were examined. On the former substrate, Geotrichum candidum NBRC 5767 showed high re-facially selective attack of hydride, while with Pichia angusta JCM 3620, complementary si-facially selective attack proceeded. G. candidum NBRC 5767 was revealed to be potent biocatalyst which provides (1′S)-alcohols from both substrates in a highly facially selective manner. Some unknown reductases were suggested responsible for those reductions, other than so far having been reported acetophenone reductase and trifluoromethyl ketone reductase from G. candidum, comparing the results obtained by applying those enzymes.
KW - Asymmetric reduction
KW - Fluoroketone
KW - Fungi
KW - Isolated enzymes
KW - Stereochemistry
KW - Yeast
UR - http://www.scopus.com/inward/record.url?scp=84863199404&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84863199404&partnerID=8YFLogxK
U2 - 10.1016/j.molcatb.2012.06.010
DO - 10.1016/j.molcatb.2012.06.010
M3 - Article
AN - SCOPUS:84863199404
VL - 82
SP - 86
EP - 91
JO - Journal of Molecular Catalysis - B Enzymatic
JF - Journal of Molecular Catalysis - B Enzymatic
SN - 1381-1177
ER -