常煦, 杨忠华, 曾嵘, 等. Production of Chiral Aromatic Alcohol by Asymmetric Reduction with Vegetable Catalyst[J]. 中国化学工程学报(英文版), 2010,18(6):1029-1033.
CHANG Xu, YANG Zhonghua, ZENG Rong, YANG Gai, YAN Jiabao. Production of Chiral Aromatic Alcohol by Asymmetric Reduction with Vegetable Catalyst[J]. , 2010, 18(6): 1029-1033.
常煦, 杨忠华, 曾嵘, 等. Production of Chiral Aromatic Alcohol by Asymmetric Reduction with Vegetable Catalyst[J]. 中国化学工程学报(英文版), 2010,18(6):1029-1033.DOI: 10.1016/S1004-9541(09)60164-6.
CHANG Xu, YANG Zhonghua, ZENG Rong, YANG Gai, YAN Jiabao. Production of Chiral Aromatic Alcohol by Asymmetric Reduction with Vegetable Catalyst[J]. , 2010, 18(6): 1029-1033.DOI: 10.1016/S1004-9541(09)60164-6.
Production of Chiral Aromatic Alcohol by Asymmetric Reduction with Vegetable Catalyst
Chiral aromatic alcohols are the key chiral building block for many important enantiopure pharmaceuticals. In this work
we studied asymmetric reduction of prochiral aromatic ketone to produce the corresponding chiral alcohol using vegetables as the biocatalyst. Acetophenone was chosen as the model substrate. The results indicate that acetophenone can be reduced to the corresponding chiral alcohols with high enantioselectivity by the chosen vegetables
i.e
. apple(
Malus pumila
)
carrot(
Daucus carota
)
cucumber(
Cucumis sativus
)
onion(
Allium cepa
)
potato(
Soanum tuberosum
)
radish(
Raphanus sativus
)
and sweet potato(
Ipomoea batatas
). In the reaction
R-1-phenylethanol is produced with apple
sweet potato and potato as the catalyst
while S-1-phenylethanol is the product with the other vegetables as the catalyst. In term of the enantioselectivity and reaction yield
carrot(
D. carota
) is the best catalyst for this reaction. Furthermore
the reaction characteristics were studied in detail using carrot(
D. carota
) as the biocatalyst. The effects of various factors on the reaction were investigated and the optimal reaction conditions were determined. Under the optimal reaction conditions(reaction time 50 h
substrate concentration 20 mmol·L
-1
reaction temperature 35℃ and pH 7)
95% of
e.e
.(to
S
-1-phenylethanol) and 85% chemical yield can be obtained. This work extends the biocatalyst for the asymmetric reduction reaction of pr
ochiral aromatic ketones
and provides a novel potential route to produce enantiopure aromatic alcohols.
关键词
Keywords
references
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Aggregation-regulated bioreduction process of graphene oxide by Shewanella bacteria
Asymmetric bioreduction of γ- and δ-keto acids by native carbonyl reductases from Saccharomyces cerevisiae
Highly efficient synthesis of (R)-1,3-butanediol via anti-Prelog reduction of 4-hydroxy-2-butanone with absolute stereoselectivity by a newly isolated Pichia kudriavzevii
Asymmetric Bioreduction of 3,5-Bis(trifluoromethyl) Acetophenone to Its Corresponding Alcohol by Candida tropicalis
Reaction Characteristics of Asymmetric Synthesis of (2S,5S)-2,5-Hexanediol Catalyzed with Baker’s Yeast Number 6
相关作者
Liang Shen
Ping Zeng
Yinghua Lu
Yibo Zeng
Kaixin Han
Yunpeng Bai
Jianhe Xu
Jiang Pan
相关机构
Department of Chemical and Biochemical Engineering, College of Chemistry and Chemical Engineering, Xiamen University
Tung Sah Institute of Micro-Nano Science and Technology, Xiamen University, Xiamen
Chinese Research Academy of Environmental Sciences
State Key Laboratory of Bioreactor Engineering
Shanghai Collaborative Innovation Centre for Biomanufacturing, East China University of Science and Technology