Chiral synthesis of the key intermediate of (+)- and (-)-thienamycin

1985 ◽  
Vol 50 (13) ◽  
pp. 2327-2331 ◽  
Author(s):  
Tetsuji Kametani ◽  
Takayasu Nagahara ◽  
Toshio Honda
Keyword(s):  
Chiral Synthesis

A chiral synthesis of (−)-cannabisativine: an application of the highly diastereo-selective hetero Diels-Alder reaction

1991 ◽  
Vol 32 (13) ◽  
pp. 1649-1652 ◽  
Author(s):  
Tatsuo Hamada ◽  
Tatsuya Zenkoh ◽  
Hiroki Sato ◽  
Osamu Yonemitsu
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Chiral Synthesis ◽  
Diels Alder Reaction

ChemInform Abstract: Synthetic Studies on the Starfish Alkaloid Imbricatine. A Chiral Synthesis of Tri-O-methylimbricatine.

ChemInform ◽  
2010 ◽  
Vol 30 (35) ◽  
pp. no-no
Author(s):  
Masashi Ohba ◽  
Yoshikazu Nishimura ◽  
Miyako Kato ◽  
Tozo Fujii
Keyword(s):  
Chiral Synthesis ◽  
Synthetic Studies

Chiral Synthesis of Furanosesquiterpene, (+)-Ipomeamarone

Heterocycles ◽  
1996 ◽  
Vol 43 (6) ◽  
pp. 1287 ◽  
Author(s):  
Keizo Matsuo ◽  
Takahiko Arase ◽  
Shigetoshi Ishida ◽  
Yusuke Sakaguchi
Keyword(s):  
Chiral Synthesis

scholarly journals Use of thiamin diphosphate‐dependent decarboxylases in chiral synthesis of carboligase products

2006 ◽  
Vol 20 (4) ◽  
Author(s):  
Ahmet Tarik Baykal ◽  
Sumit Chakraborty ◽  
Natalia Nemeria ◽  
Frank Jordan
Keyword(s):  
Thiamin Diphosphate ◽  
Chiral Synthesis

scholarly journals Efficient production of (S)-1-phenyl-1, 2-ethanediol using xylan as co-substrate by a coupled multi-enzyme Escherichia coli system

2020 ◽  
Author(s):  
Junchao Rao ◽  
Rongzhen Zhang ◽  
Guanyu Xu ◽  
Lihong Li ◽  
Yan Xu
Keyword(s):  
Escherichia Coli ◽  
Glucose Dehydrogenase ◽  
Optical Purity ◽  
Carbonyl Reductase ◽  
Cofactor Regeneration ◽  
Efficient Production ◽  
Chiral Synthesis ◽  
E Coli ◽  
Concomitant Reduction ◽  
Different Strains

Abstract Background: ( S )-1-phenyl-1,2-ethanediol is an important chiral intermediate in the synthesis of liquid crystals and chiral biphosphines.(S)-carbonyl reductase II from Candida parapsilosis catalyzes the conversion of 2-hydroxyacetophenone to ( S )-1-phenyl-1,2-ethanediol with NADPH as a cofactor. Glucose dehydrogenase with a Ala258Phe mutation is able to catalyze the oxidation of xylose with concomitant reduction of NADP + to NADPH, while endo-β-1,4-xylanase 2 catalyzes the conversion of xylan to xylose. In the present work, the Ala258Phe glucose dehydrogenase mutant and endo-β-1,4-xylanase 2 were introduced into the ( S )-carbonyl reductase II-mediated chiral pathway to strengthen cofactor regeneration by using xylan as a naturally abundant co-substrate. Results: We constructed several coupled multi-enzyme systems by introducing ( S )-carbonyl reductase II, the A258F glucose dehydrogenase mutant and endo-β-1,4-xylanase 2 into Escherichia coli . Different strains were produced by altering the location of the encoding genes on the plasmid. Only recombinant E. coli /pET-G-S-2 expressed all three enzymes, and this strain produced ( S )-1-phenyl-1,2-ethanediol from 2-hydroxyacetophenone as a substrate and xylan as a co-substrate. The optical purity was 100% and the yield was 98.3% (6 g/L 2-HAP) under optimal conditions of 35°C, pH 6.5 and a 2:1 substrate-co-substrate ratio. The introduction of A258F glucose dehydrogenase and endo-β-1,4-xylanase 2 into the ( S )-carbonyl reductase II-mediated chiral pathway caused a 54.6% increase in yield, and simultaneously reduced the reaction time from 48 h to 28 h. Conclusions: This study demonstrates efficient chiral synthesis using a pentose as a co-substrate to enhance cofactor regeneration. This provides a new approach for enantiomeric catalysis through the inclusion of naturally abundant materials.

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