Enzymes in organic synthesis. 23. Effects of organic solvents on horse liver alcohol dehydrogenase-catalyzed oxidation

The effects have been evaluated of up to 50% (v/v) of methanol, tert-butyl alcohol, dimethylsulfoxide, sulfolane, acetonitrile, dimethylformamide, N-methyl-2-pyrrolidone, hexamethylphosphoramide, acetone, 2-butanone, tetrahydrofuran, dimethoxyethane, diglyme, and dioxane on horse liver alcohol dehydrogenase (HLADH)-catalyzed oxidation of the representative alcohol substrate cyclohexanol. With the exception of dimethylsulfoxide and dimethylformamide, all solvents tested are suitable for use as cosolvents with HLADH in the oxidative and reductive directions.

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

Canadian Journal of Chemistry ◽

10.1139/v84-440 ◽

1984 ◽

Vol 62 (11) ◽

pp. 2578-2582 ◽

Cited By ~ 34

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.

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Enzymes in organic synthesis. 22. Effects of organic solvents on horse liver alcohol dehydrogenase-catalyzed reduction

Canadian Journal of Chemistry ◽

10.1139/v82-051 ◽

1982 ◽

Vol 60 (3) ◽

pp. 335-338 ◽

Cited By ~ 13

Author(s):

J. Bryan Jones ◽

Harold M. Schwartz

Keyword(s):

Alcohol Dehydrogenase ◽

Organic Synthesis ◽

Organic Solvents ◽

Horse Liver Alcohol Dehydrogenase ◽

Liver Alcohol Dehydrogenase ◽

Horse Liver ◽

Enzymes In Organic Synthesis

The effects have been evaluated of up to 30% (v/v) of methanol, ethanol, 2-propanol, tert-butylalcohol, dimethylsulfoxide, sulfolane, acetonitrile, dimethylformamide, N-methyl-2-pyrrolidone, hexamethylphosphoramide, tetrahydrofuran, dimethoxymethane, diglyme, and dioxane on horse liver alcohol dehydrogenase-catalyzed reduction of the representative ketone cyclohexanone. The most viable solvents are those shown in italics on the above list.

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Enzymes in organic synthesis. 14. Stereoselective horse liver alcohol dehydrogenase catalyzed oxidations of diols containing a prochiral centre and of related hemiacetals

Canadian Journal of Chemistry ◽

10.1139/v79-170 ◽

1979 ◽

Vol 57 (9) ◽

pp. 1025-1032 ◽

Cited By ~ 26

Author(s):

J. Bryan Jones ◽

Kar P. Lok

Keyword(s):

Alcohol Dehydrogenase ◽

Organic Synthesis ◽

Initial Oxidation ◽

Horse Liver Alcohol Dehydrogenase ◽

Liver Alcohol Dehydrogenase ◽

Horse Liver ◽

Catalyzed Oxidation ◽

Enzymes In Organic Synthesis ◽

Hydroxyethyl Group

The asymmetric synthetic potential of horse liver alcohol dehydrogenase catalyzed oxidations of variously 3-substituted pentane-1,5-diols has been further delineated. The oxidations proceed with enantiotopic selectivity to give the corresponding (3S)-3-substituted valerolactones of up to 78% ee. The reactions occur via initial oxidation of the pro-S hydroxyethyl group, with the initially-formed hydroxyaldehydes undergoing further in situ enzyme-catalyzed oxidation in their hemiacetal forms to give the (3S)-lactones directly. The hemiacetal oxidation step is also stereoselective, with oxidation of the (4S)-enantiomer being much preferred. The size of the substituent at C-3 in the diols (C-4 in the hemiacetals) affects both the enantiotopic and enantiomeric specificity of the enzyme. Both types of stereospecificity are highest when the substituents are smallest, such as methyl or ethyl, and diminish progressively for diol or hemiacetal substrates bearing large aliphatic or aromatic substituents. All reactions were carried out on a preparative (up to 2 g) scale.

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