Enzymes in organic synthesis. 31. Preparations of enantiomerically pure bicyclic [3.2.1] and [3.3.1] chiral lactones via stereospecific horse liver alcohol dehydrogenase catalyzed oxidations of meso diols

1984 ◽  
Vol 106 (5) ◽  
pp. 1461-1467 ◽  
Author(s):  
Alexander J. Bridges ◽  
P. Sundara Raman ◽  
George S. Y. Ng ◽  
J. Bryan Jones
Keyword(s):  
Alcohol Dehydrogenase ◽  
Organic Synthesis ◽  
Horse Liver Alcohol Dehydrogenase ◽  
Enantiomerically Pure ◽  
Liver Alcohol Dehydrogenase ◽  
Horse Liver ◽  
Chiral Lactones ◽  
Enzymes In Organic Synthesis

Enzymes in organic synthesis. 32. Stereospecific horse liver alcohol dehydrogenase-catalyzed oxidations of exo- and endo-oxabicyclic meso diols

1984 ◽  
Vol 62 (11) ◽  
pp. 2578-2582 ◽  
Author(s):  
J. Bryan Jones ◽  
Christopher J. Francis
Keyword(s):  
Alcohol Dehydrogenase ◽  
Organic Synthesis ◽  
Horse Liver Alcohol Dehydrogenase ◽  
Preparative Scale ◽  
Enantiomerically Pure ◽  
Liver Alcohol Dehydrogenase ◽  
Horse Liver ◽  
One Step ◽  
Catalyzed Oxidation ◽  
Enzymes In Organic Synthesis

Preparative-scale horse liver alcohol dehydrogenase-catalyzed oxidation of mesoexo- and endo-7-oxabicyclo[2.2.1]heptane diols provides a direct one-step route to enantiomerically pure chiral γ-lactones of the oxabicyclic series.

Enzymes in organic synthesis. 30. Reaction conditions – control of enantiomeric purities. Horse liver alcohol dehydrogenase-catalyzed reductions of 2-alkylcyclohexanones and their thiopyran analogs

1984 ◽  
Vol 62 (1) ◽  
pp. 77-80 ◽  
Author(s):  
J. Bryan Jones ◽  
Tetsuo Takemura
Keyword(s):  
Alcohol Dehydrogenase ◽  
Organic Synthesis ◽  
Reaction Conditions ◽  
Horse Liver Alcohol Dehydrogenase ◽  
Enantiomerically Pure ◽  
Liver Alcohol Dehydrogenase ◽  
Enzyme Substrate ◽  
Horse Liver ◽  
Substrate Ratio ◽  
Enzymes In Organic Synthesis

The effects of buffer, pH, reaction time, and [enzyme]/[substrate] ratio on the enantiomeric purities of the alcohol products of horse liver alcohol dehydrogenase-catalyzed reductions of (±)-α-alkylcyclohexanones and -tetrahydrothiopyranones have been studied. For poor substrates of this type, formation of enantiomerically pure products is assured when pH 8 and < 0.5 × 10−4 [E]/[S] ratio conditions are used.

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