Efficient Biosynthesis of (S)-1-chloro-2-heptanol Catalyzed by a Newly Isolated Fungi Curvularia hominis B-36

(S)-1-chloro-2-heptanol is an enantiopure chemical of great value that can synthesize Treprostinil for treating primary pulmonary hypertension. In this work, a new strain B-36, capable of asymmetric reduction of 1-chloro-2-heptanone to (S)-1-chloro-2-heptanol, was screened and identified as Curvular...

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Published in:Catalysts 2023-01, Vol.13 (1), p.52
Main Authors: Xu, Shenpeng, Lin, Qinzhe, Chen, Wentian, Lin, Ruoyu, Shen, Yikai, Tang, Pinchuan, Yu, Sisi, Du, Wenting, Li, Jun
Format: Article
Language:English
Subjects:
Alcohol
Asymmetry
Biocatalysts
Bioreactors
Biosynthesis
Carbohydrates
Catalysis
Catalysts
Chemical reactions
Chemical synthesis
Dry cells
Efficiency
Enzymes
High temperature
Hypertension
NMR
Nuclear magnetic resonance
Pharmaceuticals
Potassium phosphates
Selectivity
Substrates
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Summary:(S)-1-chloro-2-heptanol is an enantiopure chemical of great value that can synthesize Treprostinil for treating primary pulmonary hypertension. In this work, a new strain B-36, capable of asymmetric reduction of 1-chloro-2-heptanone to (S)-1-chloro-2-heptanol, was screened and identified as Curvularia hominis B-36 (CCTCC M 2017654) based on the morphological and internally transcribed spacer (ITS) sequence. The reductive capacity of Curvularia hominis B-36 was investigated as a whole-cell biocatalyst in the bioreduction, and the excellent yield (97.2%) and enantiomeric excess (ee) value (99.9%) were achieved under the optimal conditions as follows: 75 mM 1-chloro-2-heptanone, K2HPO4-KH2PO4 (100 mM, pH 6.0), 50 g L−1 resting cells (dry cell weight; DCW), 15% (v/v) isopropanol as co-substrate, 200 rpm, 30 °C, 20 h. The scaled-up biocatalytic process was accomplished at a bioreactor in a 1.5 L working volume, showing superb yield (~97%) and selectivity (99.9%). The product (S)-1-chloro-2-heptanol was purified and characterized by NMR. Curvularia hominis B-36 is a novel catalyst and the asymmetric synthesis route is benign and eco-friendly.
ISSN:2073-4344
2073-4344
DOI:10.3390/catal13010052